feat(maestro): show image previews in user message bubbles

Uploaded images now render as thumbnails in the user bubble instead of
showing only the server file path as text.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>

.claude/settings.local.json

@@ -0,0 +1,17 @@
+{
+  "permissions": {
+    "allow": [
+      "Bash(git add:*)",
+      "Bash(git commit:*)",
+      "Bash(git fetch:*)",
+      "Bash(git merge:*)",
+      "Bash(npx tsc:*)",
+      "Bash(npm run build:*)",
+      "Bash(npm install:*)",
+      "Bash(./node_modules/.bin/tsc:*)",
+      "Bash(npm test:*)",
+      "Bash(cargo check:*)",
+      "Bash(cargo clippy:*)"
+    ]
+  }
+}

crates/maestro-cli/src/cli.rs

@@ -41,8 +41,8 @@ pub enum Command {
     Attach(AttachArgs),
     /// Kill a session by ID.
     Kill(KillArgs),
-    /// Type text into a running session, as if it had been typed on an
+    /// Send text to a running session. Terminal sessions receive raw
-    /// attached terminal.
+    /// keystrokes; structured sessions receive an ACP prompt.
     Send(SendArgs),
     /// Install or update the agent activity hook (#106).
     Hooks(HooksArgs),

crates/maestro-cli/src/sessions.rs

@@ -130,9 +130,12 @@ pub fn resolve_session(sessions: &[Session], needle: &str) -> Result<uuid::Uuid,
 /// `maestro send`. Answers with the session that was typed into, so the
 /// caller can name it once the daemon has accepted the text.
 ///
-/// A bare ID skips the catalog fetch; anything else needs the list to match
+/// Terminal sessions get raw keystrokes via `send_input`; structured sessions
-/// against. Text comes from the arguments, or from stdin when there is none —
+/// get an ACP prompt via `send_structured_prompt` (`--no-enter` is ignored
-/// the shape a heredoc or a pipe wants.
+/// there — ACP prompts are always complete messages).
+///
+/// Text comes from the arguments, or from stdin when there is none — the
+/// shape a heredoc or a pipe wants.
 #[allow(clippy::result_large_err)]
 pub async fn run_send(
     client: &DaemonClient,
@@ -155,19 +158,28 @@ pub async fn run_send(
         return Err(CliError::NothingToSend);
     }
 
-    let id = match uuid::Uuid::parse_str(args.session.trim()) {
+    // We always need the session list: even a bare UUID needs the view field
-        Ok(id) => id,
+    // to decide which endpoint to hit.
-        Err(_) => {
+    let sessions = client.list_sessions().await?;
-            let sessions = client.list_sessions().await?;
+    let id = resolve_session(&sessions, &args.session)?;
-            resolve_session(&sessions, &args.session)?
+    let view = sessions
-        }
+        .iter()
-    };
+        .find(|s| s.id == id)
+        .map(|s| s.view)
+        .unwrap_or(SessionView::Terminal);
 
-    let req = SendInputRequest {
+    match view {
-        text,
+        SessionView::Structured => {
-        submit: !args.no_enter,
+            client.send_structured_prompt(id, &text).await?;
-    };
+        }
-    client.send_input(id, &req).await?;
+        SessionView::Terminal => {
+            let req = SendInputRequest {
+                text,
+                submit: !args.no_enter,
+            };
+            client.send_input(id, &req).await?;
+        }
+    }
     Ok(id)
 }
 
@@ -216,6 +228,7 @@ fn print_session_table(out: &mut impl Write, sessions: &[Session], info: &Daemon
             ActivityState::Idle => "idle",
             ActivityState::AwaitingInput => "awaiting",
             ActivityState::Error => "error",
+            ActivityState::Starting => "starting",
         };
         // Show the live foreground command alongside the spawn command when
         // the daemon has observed one that differs (NAP-340).

crates/maestro-cli/tests/against_mock_daemon.rs

@@ -2,7 +2,7 @@
 //! was unit-tested, but nothing exercised the client, the error decoding, or
 //! the unreachable-daemon path without compiling and forking a real daemon.
 
-use maestro_protocol::{DaemonClient, DaemonInfo};
+use maestro_protocol::{DaemonClient, DaemonInfo, SessionView};
 use maestro_testing::{session, MockDaemon};
 use uuid::Uuid;
 
@@ -202,6 +202,35 @@ async fn send_resolves_a_session_by_name() {
     assert_eq!(sent, id);
 }
 
+/// A structured session routes through the ACP prompt endpoint, not the
+/// terminal input one — `--no-enter` is irrelevant (ACP prompts are
+/// complete messages).
+#[tokio::test]
+async fn send_to_structured_session_uses_acp_prompt() {
+    let mock = MockDaemon::start().await;
+    let id = Uuid::from_u128(13);
+    let mut s = session(id, "/tmp", "claude");
+    s.view = SessionView::Structured;
+    mock.add_session(s);
+
+    let args = maestro_cli::cli::SendArgs {
+        session: id.to_string(),
+        text: vec!["fix".into(), "the".into(), "tests".into()],
+        no_enter: false,
+    };
+    let sent = maestro_cli::sessions::run_send(&mock.client(), &args, &mut std::io::empty())
+        .await
+        .expect("send");
+
+    assert_eq!(sent, id);
+    // Terminal input must stay empty — the message went through ACP.
+    assert!(mock.inputs().is_empty());
+    let prompts = mock.structured_prompts();
+    assert_eq!(prompts.len(), 1);
+    assert_eq!(prompts[0].0, id);
+    assert_eq!(prompts[0].1.prompt, "fix the tests");
+}
+
 #[tokio::test]
 async fn send_to_an_unknown_session_fails_without_typing_anything() {
     let mock = MockDaemon::start().await;

crates/maestro-daemon/src/local_api.rs

@@ -180,7 +180,7 @@ fn dir_error_status(code: &str) -> StatusCode {
 fn session_error_status(code: &str) -> StatusCode {
     match code {
         "not_found" => StatusCode::NOT_FOUND,
-        "invalid_env" => StatusCode::BAD_REQUEST,
+        "invalid_env" | "bad_request" => StatusCode::BAD_REQUEST,
         // A guard refusal is the daemon doing its job, not a failure (#79).
         "kill_guarded" => StatusCode::CONFLICT,
         // The session outlived its pane: nothing to type into, and nothing
@@ -483,7 +483,9 @@ async fn structured_prompt(
     Json(body): Json<StructuredPromptRequest>,
 ) -> Response {
     match s.manager.queue_acp_prompt(id, body.prompt).await {
-        Ok(QueueAcpPrompt::Queued) => StatusCode::NO_CONTENT.into_response(),
+        Ok(QueueAcpPrompt::Queued) | Ok(QueueAcpPrompt::Pending) => {
+            StatusCode::NO_CONTENT.into_response()
+        }
         Ok(QueueAcpPrompt::InFlight) => error_response(
             StatusCode::CONFLICT,
             "turn_in_flight",

crates/maestro-daemon/src/session.rs

@@ -6,12 +6,9 @@
 //! handler interact with tmux.
 
 use std::collections::{HashMap, HashSet};
-use std::future::Future;
 use std::path::PathBuf;
-use std::pin::Pin;
 use std::sync::atomic::{AtomicBool, AtomicU64, AtomicUsize, Ordering};
 use std::sync::{Arc, Weak};
-use std::task::{Context, Poll};
 use std::time::Duration;
 
 use chrono::Utc;
@@ -125,6 +122,9 @@ pub struct SessionRecord {
     /// When `true`, the permission pump auto-responds `AllowAlways` to every
     /// ACP permission request without surfacing it to clients.
     pub auto_approve: bool,
+    /// A prompt submitted while the adapter was still booting (`Starting`).
+    /// The background handshake task drains this on success.
+    pub pending_prompt: Option<String>,
 }
 
 impl SessionRecord {
@@ -134,6 +134,13 @@ impl SessionRecord {
             && self.acp.is_some()
             && self.acp_events.is_some()
     }
+
+    /// The session is structured and still booting its adapter.
+    fn is_starting_structured(&self) -> bool {
+        self.session.view == SessionView::Structured
+            && self.session.activity == ActivityState::Starting
+            && self.acp.is_none()
+    }
 }
 
 #[derive(Debug)]
@@ -208,6 +215,8 @@ pub enum SessionError {
     NotTerminal(Uuid),
     #[error("daemon is shutting down")]
     ShuttingDown,
+    #[error("bad request: {0}")]
+    BadRequest(String),
     /// The kill was refused (#79): the session's worktree holds unsaved work.
     /// Nothing happened — the session keeps running and the tree is untouched,
     /// so it stays the operator's handle on their own unfinished work.
@@ -227,6 +236,8 @@ pub enum BeginAcpTurn {
 #[derive(Debug)]
 pub enum QueueAcpPrompt {
     Queued,
+    /// The adapter is still booting; the prompt is held until it is ready.
+    Pending,
     InFlight,
     Unavailable,
     Failed(String),
@@ -253,6 +264,7 @@ impl SessionError {
             SessionError::NotRunning(_) => "not_running",
             SessionError::NotTerminal(_) => "not_terminal",
             SessionError::ShuttingDown => "shutting_down",
+            SessionError::BadRequest(_) => "bad_request",
             SessionError::KillGuarded(_) => "kill_guarded",
         };
         let unsaved_work = match self {
@@ -320,18 +332,6 @@ struct StructuredLifecycle {
 }
 
 impl StructuredLifecycle {
-    fn admit<'a>(
-        &'a self,
-        shutting_down: &AtomicBool,
-    ) -> Result<StructuredCreate<'a>, SessionError> {
-        let _gate = self.gate.lock().expect("structured lifecycle gate");
-        if shutting_down.load(Ordering::Acquire) {
-            return Err(SessionError::ShuttingDown);
-        }
-        self.in_flight.fetch_add(1, Ordering::AcqRel);
-        Ok(StructuredCreate { lifecycle: self })
-    }
-
     async fn wait_until_settled(&self) {
         loop {
             let settled = self.settled.notified();
@@ -343,30 +343,18 @@ impl StructuredLifecycle {
     }
 }
 
-struct StructuredCreate<'a> {
+/// Release the structured-lifecycle in-flight counter that `create` acquires
-    lifecycle: &'a StructuredLifecycle,
+/// before spawning the background ACP handshake task. Called when the task
-}
+/// finishes (success or failure) or when `create_inner` fails before the task
-
+/// is spawned.
-impl Drop for StructuredCreate<'_> {
+fn drop_structured_lifecycle_permit(inner: &Inner) {
-    fn drop(&mut self) {
+    if inner
-        if self.lifecycle.in_flight.fetch_sub(1, Ordering::AcqRel) == 1 {
+        .structured_lifecycle
-            self.lifecycle.settled.notify_one();
+        .in_flight
-        }
+        .fetch_sub(1, Ordering::AcqRel)
-    }
+        == 1
-}
+    {
-
+        inner.structured_lifecycle.settled.notify_one();
-struct AdmittedStructuredCreate<'a> {
-    create: Pin<Box<dyn Future<Output = Result<Session, SessionError>> + Send + 'a>>,
-    /// Field order matters: dropping a cancelled create rolls back its inner
-    /// future before this permit releases shutdown's in-flight barrier.
-    _permit: StructuredCreate<'a>,
-}
-
-impl Future for AdmittedStructuredCreate<'_> {
-    type Output = Result<Session, SessionError>;
-
-    fn poll(mut self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<Self::Output> {
-        self.create.as_mut().poll(cx)
     }
 }
 
@@ -660,7 +648,9 @@ impl SessionManager {
         let stream = {
             let sessions = self.inner.sessions.lock().await;
             let record = sessions.get(&id).ok_or(SessionError::NotFound(id))?;
-            if !record.is_live_structured() {
+            // Allow connecting while the adapter is still booting
+            // (`Starting`) — the event stream exists, it is just empty.
+            if !record.is_live_structured() && !record.is_starting_structured() {
                 return Ok(None);
             }
             let Some(stream) = &record.acp_events else {
@@ -745,8 +735,14 @@ impl SessionManager {
         text: String,
     ) -> Result<QueueAcpPrompt, SessionError> {
         let (acp, stream) = {
-            let sessions = self.inner.sessions.lock().await;
+            let mut sessions = self.inner.sessions.lock().await;
-            let record = sessions.get(&id).ok_or(SessionError::NotFound(id))?;
+            let record = sessions.get_mut(&id).ok_or(SessionError::NotFound(id))?;
+            // While the adapter is booting, stash the prompt for the
+            // background handshake task to drain on success.
+            if record.is_starting_structured() {
+                record.pending_prompt = Some(text);
+                return Ok(QueueAcpPrompt::Pending);
+            }
             if !record.is_live_structured() {
                 return Ok(QueueAcpPrompt::Unavailable);
             }
@@ -1217,17 +1213,42 @@ impl SessionManager {
     }
 
     /// Spawn a new session. On success returns the freshly-created `Session`.
+    ///
+    /// For structured sessions, the ACP handshake runs in a background task
+    /// after the session is registered — the HTTP caller gets an instant
+    /// response with `activity: Starting`. The `StructuredLifecycle` gate is
+    /// held across the background task so `shutdown()` waits for it.
     pub async fn create(&self, req: CreateSessionRequest) -> Result<Session, SessionError> {
         if req.view == SessionView::Structured {
-            let permit = self
+            // Acquire the lifecycle gate synchronously (rejects if shutting
+            // down). The background handshake task calls
+            // `drop_structured_lifecycle_permit` when it finishes; we must
+            // not use the RAII `StructuredCreate` because it would drop at
+            // the end of `create_inner`, before the handshake completes.
+            let _gate = self
                 .inner
                 .structured_lifecycle
-                .admit(&self.inner.shutting_down)?;
+                .gate
-            return AdmittedStructuredCreate {
+                .lock()
-                create: Box::pin(self.create_inner(req)),
+                .expect("structured lifecycle gate");
-                _permit: permit,
+            if self.inner.shutting_down.load(Ordering::Acquire) {
+                return Err(SessionError::ShuttingDown);
             }
-            .await;
+            self.inner
+                .structured_lifecycle
+                .in_flight
+                .fetch_add(1, Ordering::AcqRel);
+            drop(_gate);
+
+            return match self.create_inner(req).await {
+                Ok(session) => Ok(session),
+                Err(e) => {
+                    // create_inner failed before spawning the background
+                    // task, so release the permit here.
+                    drop_structured_lifecycle_permit(&self.inner);
+                    Err(e)
+                }
+            };
         }
         self.create_inner(req).await
     }
@@ -1289,32 +1310,39 @@ impl SessionManager {
         {
             session_env.insert("MAESTRO_URL".into(), url);
         }
-        // A structured session (#134) gets no tmux pane: the agent is a
+        // ── Structured path: validate adapter, open event log, register
-        // child of the daemon, driven over ACP. An adapter that cannot come
+        // the session immediately with `Starting`, then handshake in the
-        // up still yields a session — Dead, with the reason on it — so the
+        // background so the HTTP caller gets an instant response.
-        // operator sees what to fix instead of a silently missing session.
+        //
-        let (acp, acp_failure) = match req.view {
+        // ── Terminal path: unchanged — tmux spawn is fast enough to stay
-            SessionView::Structured => match structured_adapter(&req.command) {
+        // synchronous.
-                Err(error) => (None, Some(error)),
+        // Structured: validate adapter, open event log eagerly. Terminal:
-                Ok(adapter) => match maestro_acp::spawn(
+        // spawn the tmux pane synchronously (it is fast).
-                    SpawnConfig::new(
+        let structured_spawn = match req.view {
-                        &effective_cwd,
+            SessionView::Structured => {
-                        session_env
+                // Fail fast on an unsupported command before touching disk.
-                            .iter()
+                let adapter = structured_adapter(&req.command).map_err(SessionError::BadRequest)?;
-                            .map(|(k, v)| (k.clone(), v.clone()))
+                // Open the event log eagerly so the structured WS can
-                            .collect(),
+                // connect before the adapter is up.
-                    )
+                let acp_events = match self.inner.sidecar.open_events(id) {
-                    .adapter(adapter),
+                    Ok(log) => {
-                )
+                        let (tx, _) = broadcast::channel(EVENTS_CAPACITY);
-                .await
+                        let (projected_tx, _) = broadcast::channel(EVENTS_CAPACITY);
-                {
+                        Arc::new(Mutex::new(AcpEventStream {
-                    Ok(acp) => (Some(Arc::new(acp)), None),
+                            log,
-                    Err(e) => {
+                            live: tx,
-                        tracing::warn!(%id, error = %e, "structured session: adapter failed to start");
+                            projection: Projection::default(),
-                        (None, Some(e.to_string()))
+                            projected_live: projected_tx,
+                            pending_approvals: HashMap::new(),
+                            operation: Arc::new(Mutex::new(())),
+                            dispatch: AcpDispatchState::default(),
+                            activity_sequence: 0,
+                        }))
                     }
-                },
+                    Err(e) => return Err(SessionError::Sidecar(e)),
-            },
+                };
+                Some((adapter, acp_events))
+            }
             SessionView::Terminal => {
                 let spawned = {
                     let tmux = self.inner.tmux.clone();
@@ -1328,53 +1356,10 @@ impl SessionManager {
                 if let Err(e) = spawned {
                     return Err(SessionError::Tmux(e));
                 }
-                (None, None)
+                None
             }
         };
 
-        let acp_events = if let Some(acp) = &acp {
-            let persisted =
-                match self
-                    .inner
-                    .sidecar
-                    .read_events(id, EventCursor::Since(0), usize::MAX)
-                {
-                    Ok(events) => events,
-                    Err(error) => {
-                        acp.terminate(maestro_acp::CANCEL_GRACE, maestro_acp::TERM_GRACE)
-                            .await;
-                        return Err(SessionError::Sidecar(error));
-                    }
-                };
-            match self.inner.sidecar.open_events(id) {
-                Ok(log) => {
-                    let (tx, _) = broadcast::channel(EVENTS_CAPACITY);
-                    let (projected_tx, _) = broadcast::channel(EVENTS_CAPACITY);
-                    let mut projection = Projection::default();
-                    for event in &persisted {
-                        apply_persisted_event(&mut projection, event);
-                    }
-                    Some(Arc::new(Mutex::new(AcpEventStream {
-                        log,
-                        live: tx,
-                        projection,
-                        projected_live: projected_tx,
-                        pending_approvals: HashMap::new(),
-                        operation: Arc::new(Mutex::new(())),
-                        dispatch: AcpDispatchState::default(),
-                        activity_sequence: 0,
-                    })))
-                }
-                Err(e) => {
-                    acp.terminate(maestro_acp::CANCEL_GRACE, maestro_acp::TERM_GRACE)
-                        .await;
-                    return Err(SessionError::Sidecar(e));
-                }
-            }
-        } else {
-            None
-        };
-
         // Capture spawn-history inputs before `req` is partially moved into
         // `session`. `history_cwd` is the *chosen* working dir (the request
         // `cwd`), not a generated worktree checkout path — that's what the
@@ -1384,10 +1369,13 @@ impl SessionManager {
         resolve_name(&mut metadata);
         let worktree_branch = req.worktree.as_ref().map(|w| w.branch.clone());
 
+        let is_structured = structured_spawn.is_some();
+        let events_arc = structured_spawn.as_ref().map(|(_, e)| e.clone());
+
         let session = Session {
             id,
-            cwd: effective_cwd,
+            cwd: effective_cwd.clone(),
-            command: req.command,
+            command: req.command.clone(),
             env: req.env,
             metadata,
             worktree: worktree_path.as_ref().zip(worktree_base_repo.as_ref()).map(
@@ -1396,67 +1384,41 @@ impl SessionManager {
                     base_repo: base_repo.clone(),
                 },
             ),
-            status: if acp_failure.is_some() {
+            status: SessionStatus::Running,
-                SessionStatus::Dead
-            } else {
-                SessionStatus::Running
-            },
             created_at: Utc::now(),
-            // A terminal spawn begins active until its watcher sees otherwise;
-            // a structured spawn has no turn yet and begins idle.
             foreground: None,
-            activity: match (req.view, acp_failure.is_some()) {
+            activity: if is_structured {
-                (_, true) => ActivityState::Error,
+                ActivityState::Starting
-                (SessionView::Structured, false) => ActivityState::Idle,
+            } else {
-                (SessionView::Terminal, false) => ActivityState::Active,
+                ActivityState::Active
             },
-            activity_detail: acp_failure,
+            activity_detail: None,
             last_activity_at: Utc::now(),
             activity_since: chrono::Utc::now(),
-
             current_cwd: None,
-            // The watcher fills this in on its first blocked-work pass; a
-            // fresh tree has nothing in the way anyway.
             blocked_work: None,
             last_focused_at: None,
-            acp_session_id: acp.as_ref().map(|a| a.session_id().to_string()),
+            acp_session_id: None,
             view: req.view,
         };
 
         if let Err(e) = self.inner.sidecar.write(&session) {
-            // The process already started; end it so no ghost survives a
+            if !is_structured {
-            // failed sidecar write, then unwind the FIFO + worktree.
+                let tmux = self.inner.tmux.clone();
-            match &acp {
+                let _ = tmux_blocking(move || tmux.kill_session(id)).await;
-                Some(acp) => {
-                    acp.terminate(maestro_acp::CANCEL_GRACE, maestro_acp::TERM_GRACE)
-                        .await
-                }
-                None => {
-                    let tmux = self.inner.tmux.clone();
-                    let _ = tmux_blocking(move || tmux.kill_session(id)).await;
-                }
             }
             return Err(SessionError::Sidecar(e));
         }
 
-        let event_pump = acp
-            .as_ref()
-            .zip(acp_events.as_ref())
-            .map(|(acp, events)| (acp.clone(), events.clone()));
         {
             let mut sessions = self.inner.sessions.lock().await;
-            let event_pump = event_pump.map(|(acp, events)| {
-                let done = start_acp_event_pump(&self.inner, id, &acp, events.clone());
-                start_acp_permission_pump(&self.inner, id, &acp, events, req.auto_approve);
-                done
-            });
             sessions.insert(
                 id,
                 SessionRecord {
                     session: session.clone(),
                     fifo_path,
-                    worktree_path,
+                    worktree_path: worktree_path.clone(),
-                    worktree_base_repo,
+                    worktree_base_repo: worktree_base_repo.clone(),
                     bridge,
                     reported_activity: None,
                     settled: false,
@@ -1464,11 +1426,12 @@ impl SessionManager {
                     naming: false,
                     focused_since: None,
                     awaiting_suppressed: false,
-                    acp,
+                    acp: None,
-                    acp_events,
+                    acp_events: events_arc,
                     structured_activity_watermark: None,
-                    acp_event_pump: event_pump,
+                    acp_event_pump: None,
                     auto_approve: req.auto_approve,
+                    pending_prompt: None,
                 },
             );
         }
@@ -1497,6 +1460,78 @@ impl SessionManager {
         }
 
         pending.commit();
+
+        // ── Background ACP handshake for structured sessions ──
+        //
+        // The session is registered and visible to clients. The adapter
+        // spawn + handshake runs in a background task; on completion it
+        // fills in `acp`, starts the event/permission pumps, and
+        // transitions activity from `Starting` to `Idle` (or to `Error`
+        // on failure). The `StructuredLifecycle` permit is held until the
+        // task finishes so `shutdown()` waits for it.
+        if let Some((adapter, events)) = structured_spawn {
+            let inner = self.inner.clone();
+            let env: HashMap<String, String> = session_env
+                .iter()
+                .map(|(k, v)| (k.clone(), v.clone()))
+                .collect();
+            let cwd = effective_cwd;
+            let auto_approve = req.auto_approve;
+            tokio::spawn(async move {
+                let result = maestro_acp::spawn(SpawnConfig::new(&cwd, env).adapter(adapter)).await;
+
+                match result {
+                    Ok(acp_session) => {
+                        let acp = Arc::new(acp_session);
+                        let done = start_acp_event_pump(&inner, id, &acp, events.clone());
+                        start_acp_permission_pump(&inner, id, &acp, events.clone(), auto_approve);
+                        // Drain any prompt submitted while Starting.
+                        let pending_prompt = {
+                            let mut sessions = inner.sessions.lock().await;
+                            let Some(record) = sessions.get_mut(&id) else {
+                                // Session was killed while we were booting.
+                                acp.terminate(maestro_acp::CANCEL_GRACE, maestro_acp::TERM_GRACE)
+                                    .await;
+                                drop_structured_lifecycle_permit(&inner);
+                                return;
+                            };
+                            record.acp = Some(acp.clone());
+                            record.acp_event_pump = Some(done);
+                            record.session.acp_session_id = Some(acp.session_id().to_string());
+                            record.session.activity = ActivityState::Idle;
+                            record.session.activity_since = Utc::now();
+                            let _ = inner.sidecar.write(&record.session);
+                            let _ = inner.events.send(CatalogEvent::SessionUpdated {
+                                session: record.session.clone(),
+                            });
+                            record.pending_prompt.take()
+                        };
+                        if let Some(prompt) = pending_prompt {
+                            let manager = SessionManager {
+                                inner: inner.clone(),
+                            };
+                            let _ = manager.queue_acp_prompt(id, prompt).await;
+                        }
+                    }
+                    Err(e) => {
+                        tracing::warn!(%id, error = %e, "structured session: adapter failed to start");
+                        let mut sessions = inner.sessions.lock().await;
+                        if let Some(record) = sessions.get_mut(&id) {
+                            record.session.status = SessionStatus::Dead;
+                            record.session.activity = ActivityState::Error;
+                            record.session.activity_detail = Some(e.to_string());
+                            record.session.activity_since = Utc::now();
+                            let _ = inner.sidecar.write(&record.session);
+                            let _ = inner.events.send(CatalogEvent::SessionUpdated {
+                                session: record.session.clone(),
+                            });
+                        }
+                    }
+                }
+                drop_structured_lifecycle_permit(&inner);
+            });
+        }
+
         Ok(session)
     }
 
@@ -1682,6 +1717,7 @@ impl SessionManager {
                     structured_activity_watermark: None,
                     acp_event_pump: None,
                     auto_approve: false,
+                    pending_prompt: None,
                 },
             );
             let _ = self
@@ -1862,6 +1898,7 @@ impl SessionManager {
                     // Recovery cannot know the original preset's flag; the
                     // operator re-enables it by restarting with the preset.
                     auto_approve: false,
+                    pending_prompt: None,
                 },
             );
             if let Some((acp, events)) = event_pump {
@@ -2321,6 +2358,11 @@ async fn apply_structured_activity(
     if record.session.view != SessionView::Structured {
         return;
     }
+    // While the adapter is still booting, the background handshake task
+    // owns the activity state — the activity pass must not overwrite it.
+    if record.session.activity == ActivityState::Starting {
+        return;
+    }
     let current_events = record.acp_events.as_ref();
     match (expected_events, current_events) {
         (Some((expected, sequence)), Some(current)) if Arc::ptr_eq(expected, current) => {
@@ -2586,6 +2628,12 @@ async fn run_liveness_pass(inner: &Arc<Inner>) {
         let mut tmux_backed = Vec::new();
         let mut acp_backed = Vec::new();
         for (id, record) in running {
+            if record.is_starting_structured() {
+                // The adapter hasn't finished its handshake yet — no ACP
+                // handle and no tmux pane. Skip; the background task owns
+                // this session's lifecycle until the handshake settles.
+                continue;
+            }
             match &record.acp {
                 Some(acp) => acp_backed.push((*id, acp.clone())),
                 None => tmux_backed.push(*id),

crates/maestro-daemon/tests/acp.rs

@@ -130,6 +130,25 @@ async fn wait_for_exit(pid: u32) {
     assert!(!pid_alive(pid), "pid {pid} still alive");
 }
 
+/// Wait for a session's background ACP handshake to complete (activity
+/// transitions out of `Starting`). Returns the refreshed session.
+async fn wait_for_ready(manager: &SessionManager, id: uuid::Uuid) -> maestro_protocol::Session {
+    let deadline = Instant::now() + Duration::from_secs(10);
+    loop {
+        let session = manager
+            .snapshot()
+            .await
+            .into_iter()
+            .find(|s| s.id == id)
+            .expect("session exists");
+        if session.activity != ActivityState::Starting {
+            return session;
+        }
+        assert!(Instant::now() < deadline, "handshake timed out");
+        tokio::time::sleep(Duration::from_millis(20)).await;
+    }
+}
+
 #[tokio::test]
 async fn structured_spawn_starts_the_adapter_in_cwd_with_session_env() {
     let fx = DaemonFixture::new();
@@ -138,7 +157,7 @@ async fn structured_spawn_starts_the_adapter_in_cwd_with_session_env() {
     let mut env = fake.env();
     env.insert("FAKE_ACP_ECHO_ENV".into(), "MAESTRO_SESSION_ID".into());
 
-    let session = fx
+    let created = fx
         .manager
         .create(structured_command(
             cwd.path(),
@@ -148,8 +167,12 @@ async fn structured_spawn_starts_the_adapter_in_cwd_with_session_env() {
         .await
         .expect("create");
 
-    assert_eq!(session.view, SessionView::Structured);
+    assert_eq!(created.view, SessionView::Structured);
-    assert_eq!(session.status, SessionStatus::Running);
+    assert_eq!(created.status, SessionStatus::Running);
+    assert_eq!(created.activity, ActivityState::Starting);
+    assert!(created.acp_session_id.is_none());
+
+    let session = wait_for_ready(&fx.manager, created.id).await;
     assert_eq!(session.activity, ActivityState::Idle);
     let acp_id = session.acp_session_id.clone().expect("acp session id");
     assert!(acp_id.starts_with("fake-"), "{acp_id}");
@@ -164,7 +187,7 @@ async fn structured_spawn_starts_the_adapter_in_cwd_with_session_env() {
         "{log}"
     );
     assert!(
-        log.contains(&format!("env MAESTRO_SESSION_ID={}", session.id)),
+        log.contains(&format!("env MAESTRO_SESSION_ID={}", created.id)),
         "{log}"
     );
 
@@ -232,6 +255,7 @@ async fn structured_activity_tracks_turn_completion_and_failure() {
         .create(structured_command(cwd.path(), env, "codex"))
         .await
         .unwrap();
+    let session = wait_for_ready(&fx.manager, session.id).await;
 
     assert!(matches!(
         fx.manager
@@ -295,11 +319,12 @@ async fn projection_snapshot_and_live_stream_share_one_fold() {
     let fx = DaemonFixture::new();
     let fake = Fake::new();
     let cwd = TempDir::new().unwrap();
-    let session = fx
+    let created = fx
         .manager
         .create(structured(cwd.path(), fake.env()))
         .await
         .expect("create");
+    let session = wait_for_ready(&fx.manager, created.id).await;
 
     wait_for_async(Duration::from_secs(5), || async {
         fx.manager
@@ -397,6 +422,7 @@ async fn queued_prompt_is_a_durable_user_transcript_row() {
         .create(structured(cwd.path(), fake.env()))
         .await
         .expect("create");
+    let session = wait_for_ready(&fx.manager, session.id).await;
 
     assert!(matches!(
         fx.manager
@@ -442,6 +468,7 @@ async fn stale_turn_completion_cannot_end_the_next_turn() {
         .create(structured(cwd.path(), fake.env()))
         .await
         .unwrap();
+    wait_for_ready(&fx.manager, session.id).await;
 
     let maestro_daemon::session::BeginAcpTurn::Started(_, first) =
         fx.manager.begin_acp_turn(session.id).await.unwrap()
@@ -485,6 +512,7 @@ async fn cancelled_prompt_that_never_settles_fails_the_session() {
         .create(structured(cwd.path(), env))
         .await
         .unwrap();
+    wait_for_ready(&fx.manager, session.id).await;
 
     assert!(matches!(
         fx.manager
@@ -523,6 +551,7 @@ async fn cancellation_settlement_allows_the_next_prompt_permission() {
         .create(structured(cwd.path(), env))
         .await
         .unwrap();
+    wait_for_ready(&fx.manager, session.id).await;
 
     assert!(matches!(
         fx.manager
@@ -582,11 +611,12 @@ async fn recovery_loads_the_acp_session_without_duplicating_history() {
     let mut env = fake.env();
     env.insert("FAKE_ACP_LOAD_REPLAY".into(), "2".into());
 
-    let session = fx
+    let created = fx
         .manager
         .create(structured_command(cwd.path(), env, "codex"))
         .await
         .expect("create");
+    let session = wait_for_ready(&fx.manager, created.id).await;
     let acp_id = session.acp_session_id.clone().expect("acp id");
     wait_for_async(Duration::from_secs(5), || async {
         fx.manager
@@ -711,6 +741,7 @@ async fn shutdown_preserves_a_pristine_structured_worktree_for_recovery() {
         .await
         .expect("create");
     assert_eq!(session.cwd, worktree);
+    wait_for_ready(&fx.manager, session.id).await;
     push_all_to_origin(repo.path(), origin.path());
 
     fx.manager.shutdown().await;
@@ -759,6 +790,7 @@ async fn failed_recovery_cleans_its_fifo() {
         .create(structured(cwd.path(), fake.env()))
         .await
         .expect("create");
+    wait_for_ready(&fx.manager, session.id).await;
     let old_pid = fake.pid();
     fx.manager.shutdown().await;
     wait_for_exit(old_pid).await;
@@ -792,12 +824,15 @@ async fn missing_adapter_yields_a_failed_session_naming_the_install_command() {
         empty.path().to_string_lossy().into_owned(),
     )]);
 
-    let session = fx
+    let created = fx
         .manager
         .create(structured_command(cwd.path(), env, "codex"))
         .await
-        .expect("a failed session, not an error");
+        .expect("create registers a Starting session");
+    assert_eq!(created.activity, ActivityState::Starting);
 
+    // The background handshake fails because the adapter binary is missing.
+    let session = wait_for_ready(&fx.manager, created.id).await;
     assert_eq!(session.status, SessionStatus::Dead);
     assert_eq!(session.activity, ActivityState::Error);
     let detail = session.activity_detail.clone().expect("actionable detail");
@@ -810,13 +845,13 @@ async fn missing_adapter_yields_a_failed_session_naming_the_install_command() {
 
     // It is a real session: listed, on disk, and dismissable like any other
     // dead one.
-    assert!(fx.manager.has(session.id).await);
+    assert!(fx.manager.has(created.id).await);
     assert!(fx
         .sidecar_dir()
-        .join(format!("{}.json", session.id))
+        .join(format!("{}.json", created.id))
         .exists());
-    fx.manager.kill(session.id, false).await.expect("dismiss");
+    fx.manager.kill(created.id, false).await.expect("dismiss");
-    assert!(!fx.manager.has(session.id).await);
+    assert!(!fx.manager.has(created.id).await);
 }
 
 #[tokio::test]
@@ -825,20 +860,20 @@ async fn unsupported_structured_command_fails_without_launching_claude() {
     let fake = Fake::new();
     let cwd = TempDir::new().unwrap();
 
-    let session = fx
+    let err = fx
         .manager
         .create(structured_command(cwd.path(), fake.env(), "opencode"))
         .await
-        .expect("failed structured session is persisted");
+        .expect_err("unsupported command is rejected at request validation");
 
-    assert_eq!(session.status, SessionStatus::Dead);
+    assert!(
-    let detail = session.activity_detail.expect("selection error");
+        matches!(err, maestro_daemon::SessionError::BadRequest(ref msg) if msg.contains("Claude Code or Codex")),
-    assert!(detail.contains("Claude Code or Codex"), "{detail}");
+        "{err:?}"
+    );
     assert!(
         fake.log().is_empty(),
         "unsupported command launched an adapter"
     );
-    fx.manager.kill(session.id, false).await.expect("dismiss");
 }
 
 #[tokio::test]
@@ -853,6 +888,7 @@ async fn kill_sends_cancel_then_sigterm_and_removes_the_sidecar() {
         .create(structured(cwd.path(), fake.env()))
         .await
         .expect("create");
+    wait_for_ready(&fx.manager, session.id).await;
     let pid = fake.pid();
     assert!(pid_alive(pid));
 
@@ -895,6 +931,8 @@ async fn shutdown_reaps_every_adapter_child() {
         .create(structured(cwd.path(), b.env()))
         .await
         .expect("create b");
+    wait_for_ready(&fx.manager, sa.id).await;
+    wait_for_ready(&fx.manager, sb.id).await;
     let (pa, pb) = (a.pid(), b.pid());
     assert!(pid_alive(pa) && pid_alive(pb));
 
@@ -929,10 +967,13 @@ async fn dismissal_during_shutdown_does_not_restore_recovery_artifacts() {
         .create(structured(cwd.path(), env))
         .await
         .expect("create");
-    fx.manager
+    let blocker_session = fx
+        .manager
         .create(structured(cwd.path(), blocker.env()))
         .await
         .expect("create blocker");
+    wait_for_ready(&fx.manager, session.id).await;
+    wait_for_ready(&fx.manager, blocker_session.id).await;
 
     let manager = fx.manager.clone();
     let shutdown = tokio::spawn(async move { manager.shutdown().await });
@@ -984,6 +1025,7 @@ async fn shutdown_does_not_recover_an_adapter_that_already_exited() {
         .create(structured(cwd.path(), env))
         .await
         .expect("create");
+    wait_for_ready(&fx.manager, session.id).await;
     wait_for_exit(fake.pid()).await;
 
     fx.manager.shutdown().await;
@@ -1017,23 +1059,31 @@ async fn shutdown_waits_for_structured_creation_and_rejects_new_creates() {
     let mut env = fake.env();
     env.insert("FAKE_ACP_DELAY_SESSION_NEW_MS".into(), "500".into());
 
-    let create_cwd = cwd.path().to_path_buf();
+    // create() returns immediately; the handshake runs in the background
-    let manager = fx.manager.clone();
+    // and holds a lifecycle permit.
-    let create = tokio::spawn(async move { manager.create(structured(&create_cwd, env)).await });
+    let session = fx
+        .manager
+        .create(structured(cwd.path(), env))
+        .await
+        .expect("create");
+
+    // Wait until the adapter has received session/new (handshake in progress).
     wait_for_async(Duration::from_secs(5), || async {
         fake.log().contains("recv session/new")
     })
     .await;
 
+    // Shutdown must wait for the in-flight background handshake.
     let manager = fx.manager.clone();
     let shutdown = tokio::spawn(async move { manager.shutdown().await });
     tokio::time::sleep(Duration::from_millis(50)).await;
     assert!(
         !shutdown.is_finished(),
-        "shutdown returned before create finished"
+        "shutdown returned before handshake finished"
     );
 
-    let session = create.await.expect("create task").expect("create");
+    // The handshake completes in the background (500ms delay).
+    wait_for_ready(&fx.manager, session.id).await;
     let pid = fake.pid();
     shutdown.await.expect("shutdown task");
 
@@ -1066,27 +1116,37 @@ async fn structured_handshakes_run_independently() {
         gate.to_string_lossy().into_owned(),
     );
 
-    let first_cwd = cwd.path().to_path_buf();
+    // Both create() calls return immediately with Starting; the first
-    let manager = fx.manager.clone();
+    // adapter's handshake is gated while the second runs freely.
-    let first =
+    let first = fx
-        tokio::spawn(async move { manager.create(structured(&first_cwd, blocked_env)).await });
+        .manager
-    wait_for_async(Duration::from_secs(5), || async {
+        .create(structured(cwd.path(), blocked_env))
-        blocked.log().contains("recv session/new")
+        .await
-    })
+        .expect("first create");
-    .await;
+    let second = fx
+        .manager
+        .create(structured(cwd.path(), ready.env()))
+        .await
+        .expect("second create");
 
-    let second = tokio::time::timeout(
+    // The second handshake completes independently of the first.
-        Duration::from_secs(5),
+    let second_ready = wait_for_ready(&fx.manager, second.id).await;
-        fx.manager.create(structured(cwd.path(), ready.env())),
+    assert_eq!(second_ready.activity, ActivityState::Idle);
-    )
+
-    .await
+    // The first handshake is still blocked.
-    .expect("second handshake was blocked by the first")
+    let first_snap = fx
-    .expect("second create");
+        .manager
-    assert_eq!(second.status, SessionStatus::Running);
+        .snapshot()
-    assert!(!first.is_finished(), "the gate must still block the first");
+        .await
+        .into_iter()
+        .find(|s| s.id == first.id)
+        .unwrap();
+    assert_eq!(first_snap.activity, ActivityState::Starting);
 
     std::fs::write(&gate, b"release").unwrap();
-    let first = first.await.expect("first task").expect("first create");
+    let first_ready = wait_for_ready(&fx.manager, first.id).await;
+    assert_eq!(first_ready.activity, ActivityState::Idle);
+
     fx.manager.kill(first.id, false).await.expect("kill first");
     fx.manager
         .kill(second.id, false)
@@ -1114,16 +1174,18 @@ async fn shutdown_waits_for_every_admitted_structured_create() {
         gate_b.to_string_lossy().into_owned(),
     );
 
-    let create_a = {
+    // Both create() calls return immediately; the background handshake
-        let manager = fx.manager.clone();
+    // tasks hold lifecycle permits and are blocked on their gates.
-        let cwd = cwd.path().to_path_buf();
+    let session_a = fx
-        tokio::spawn(async move { manager.create(structured(&cwd, env_a)).await })
+        .manager
-    };
+        .create(structured(cwd.path(), env_a))
-    let create_b = {
+        .await
-        let manager = fx.manager.clone();
+        .expect("create a");
-        let cwd = cwd.path().to_path_buf();
+    let session_b = fx
-        tokio::spawn(async move { manager.create(structured(&cwd, env_b)).await })
+        .manager
-    };
+        .create(structured(cwd.path(), env_b))
+        .await
+        .expect("create b");
     wait_for_async(Duration::from_secs(5), || async {
         a.log().contains("recv session/new") && b.log().contains("recv session/new")
     })
@@ -1143,14 +1205,14 @@ async fn shutdown_waits_for_every_admitted_structured_create() {
     assert!(!shutdown.is_finished());
 
     std::fs::write(&gate_a, b"release").unwrap();
-    let session_a = create_a.await.expect("create a task").expect("create a");
+    wait_for_ready(&fx.manager, session_a.id).await;
     assert!(
         !shutdown.is_finished(),
         "shutdown ignored the second create"
     );
 
     std::fs::write(&gate_b, b"release").unwrap();
-    let session_b = create_b.await.expect("create b task").expect("create b");
+    wait_for_ready(&fx.manager, session_b.id).await;
     shutdown.await.expect("shutdown task");
 
     wait_for_exit(a.pid()).await;
@@ -1166,7 +1228,7 @@ async fn shutdown_waits_for_every_admitted_structured_create() {
 }
 
 #[tokio::test]
-async fn cancelling_a_structured_handshake_rolls_back_and_settles_admission() {
+async fn killing_a_starting_session_rolls_back_and_settles_admission() {
     let fx = DaemonFixture::new();
     let fake = Fake::new();
     let repo = TempDir::new().unwrap();
@@ -1192,40 +1254,30 @@ async fn cancelling_a_structured_handshake_rolls_back_and_settles_admission() {
         auto_approve: false,
     };
 
-    let create = {
+    // create() returns immediately with Starting; the handshake is gated.
-        let manager = fx.manager.clone();
+    let session = fx.manager.create(request).await.expect("create");
-        tokio::spawn(async move { manager.create(request).await })
+    assert_eq!(session.activity, ActivityState::Starting);
-    };
     wait_for_async(Duration::from_secs(5), || async {
         fake.log().contains("recv session/new")
     })
     .await;
-    let id = fake
-        .log()
-        .lines()
-        .find_map(|line| line.strip_prefix("env MAESTRO_SESSION_ID="))
-        .and_then(|id| uuid::Uuid::parse_str(id).ok())
-        .expect("session id in adapter log");
     let pid = fake.pid();
 
-    create.abort();
+    // Kill the session while its handshake is still in progress.
-    let shutdown = {
+    // force=true because the worktree has an unpushed branch commit.
-        let manager = fx.manager.clone();
+    fx.manager.kill(session.id, true).await.expect("kill");
-        tokio::spawn(async move { manager.shutdown().await })
+
-    };
+    // Release the gate so the background task can finish and settle.
-    assert!(create.await.unwrap_err().is_cancelled());
+    std::fs::write(&gate, b"release").unwrap();
-    tokio::time::timeout(Duration::from_secs(5), shutdown)
+
+    // Shutdown must not hang — the lifecycle permit is settled.
+    tokio::time::timeout(Duration::from_secs(5), fx.manager.shutdown())
         .await
-        .expect("cancelled admission kept shutdown waiting")
+        .expect("shutdown hung on a settled permit");
-        .expect("shutdown task");
+
     wait_for_exit(pid).await;
-    wait_for_async(Duration::from_secs(5), || async {
-        !fx.fifo_dir().join(format!("{id}.fifo")).exists()
-            && !repo.path().join("cancelled-create").exists()
-    })
-    .await;
     assert!(fx.manager.snapshot().await.is_empty());
-    let id = id.to_string();
+    let id = session.id.to_string();
     assert!(
         std::fs::read_dir(fx.sidecar_dir())
             .into_iter()
@@ -1235,7 +1287,7 @@ async fn cancelling_a_structured_handshake_rolls_back_and_settles_admission() {
                 .file_name()
                 .to_string_lossy()
                 .starts_with(&id)),
-        "cancelled create left a sidecar artifact"
+        "killed Starting session left a sidecar artifact"
     );
 }
 
@@ -1252,6 +1304,7 @@ async fn shutdown_drains_final_notifications_to_the_log() {
         .create(structured(cwd.path(), env))
         .await
         .expect("create");
+    wait_for_ready(&fx.manager, session.id).await;
     wait_for_async(Duration::from_secs(5), || async {
         fx.manager
             .read_acp_events(session.id, EventCursor::Since(0), 10)
@@ -1282,6 +1335,7 @@ async fn adapter_exit_marks_the_session_dead_and_keeps_it_listed() {
         .create(structured(cwd.path(), fake.env()))
         .await
         .expect("create");
+    wait_for_ready(&fx.manager, session.id).await;
     fx.manager.start_liveness_watcher(Duration::from_millis(50));
 
     // The agent dies out from under the daemon: the liveness pass, not tmux,

crates/maestro-daemon/tests/local_api.rs

@@ -154,7 +154,8 @@ async fn structured_session(h: &Harness, fake: &FakeAcp) -> Uuid {
 }
 
 async fn structured_session_with_env(h: &Harness, env: HashMap<String, String>) -> Uuid {
-    h.manager
+    let id = h
+        .manager
         .create(CreateSessionRequest {
             view: SessionView::Structured,
             cwd: "/tmp".into(),
@@ -166,7 +167,9 @@ async fn structured_session_with_env(h: &Harness, env: HashMap<String, String>)
         })
         .await
         .unwrap()
-        .id
+        .id;
+    wait_for_session_activity(h, id, ActivityState::Idle).await;
+    id
 }
 
 async fn wait_for_session_activity(h: &Harness, id: Uuid, expected: ActivityState) {
@@ -1494,6 +1497,12 @@ async fn events_ws_streams_structured_activity_without_hook_overrides() {
     let maestro_protocol::CatalogEvent::SessionAdded { session } = next_event(&mut ws).await else {
         panic!("expected structured SessionAdded")
     };
+    assert_eq!(session.activity, ActivityState::Starting);
+    // The background handshake completes and sends SessionUpdated → Idle.
+    let maestro_protocol::CatalogEvent::SessionUpdated { session } = next_event(&mut ws).await
+    else {
+        panic!("expected SessionUpdated after handshake")
+    };
     assert_eq!(session.activity, ActivityState::Idle);
 
     let client = reqwest::Client::new();

crates/maestro-protocol/src/lib.rs

@@ -175,6 +175,10 @@ pub enum ActivityState {
     AwaitingInput,
     /// An agent reported a failure, or a structured session/turn failed.
     Error,
+    /// The ACP adapter is booting; the session is registered but cannot accept
+    /// prompts yet. Older clients that do not know this variant degrade it to
+    /// `Idle` via the lenient deserializer — acceptable.
+    Starting,
 }
 
 impl<'de> Deserialize<'de> for ActivityState {
@@ -187,6 +191,7 @@ impl<'de> Deserialize<'de> for ActivityState {
             "Active" => Self::Active,
             "AwaitingInput" => Self::AwaitingInput,
             "Error" => Self::Error,
+            "Starting" => Self::Starting,
             // Known or not, any other spelling degrades to the neutral default
             _ => Self::Idle,
         })
@@ -225,9 +230,10 @@ where
         "Idle" => Ok(ActivityState::Idle),
         "AwaitingInput" => Ok(ActivityState::AwaitingInput),
         "Error" => Ok(ActivityState::Error),
+        "Starting" => Ok(ActivityState::Starting),
         other => Err(D::Error::unknown_variant(
             other,
-            &["Active", "Idle", "AwaitingInput", "Error"],
+            &["Active", "Idle", "AwaitingInput", "Error", "Starting"],
         )),
     }
 }

crates/maestro-testing/src/lib.rs

@@ -22,7 +22,8 @@ use chrono::Utc;
 use futures_util::{SinkExt, StreamExt};
 use maestro_protocol::{
     routes, ApiError, CatalogEvent, CreateSessionRequest, DaemonClient, DaemonInfo, DirListing,
-    GitRoot, RecentDirs, SendInputRequest, Session, SessionStatus, PROTOCOL_VERSION,
+    GitRoot, RecentDirs, SendInputRequest, Session, SessionStatus, StructuredPromptRequest,
+    PROTOCOL_VERSION,
 };
 use tokio::net::TcpListener;
 use tokio::sync::{broadcast, oneshot};
@@ -60,6 +61,8 @@ struct Inner {
     forced_error: Option<(u16, ApiError)>,
     /// Everything `POST /api/sessions/:id/input` was asked to type, in order.
     inputs: Vec<(Uuid, SendInputRequest)>,
+    /// Every ACP prompt sent to a structured session, in order.
+    structured_prompts: Vec<(Uuid, StructuredPromptRequest)>,
 }
 
 #[derive(Clone)]
@@ -92,6 +95,10 @@ impl MockDaemon {
             .route(routes::SESSIONS, get(list_sessions).post(create_session))
             .route(routes::patterns::SESSION, delete(kill_session))
             .route(routes::patterns::SESSION_INPUT, post(send_input))
+            .route(
+                routes::patterns::STRUCTURED_PROMPT,
+                post(structured_prompt),
+            )
             .route(routes::INFO, get(daemon_info))
             .route(routes::DIRS, get(list_dir))
             .route(routes::RECENT_DIRS, get(recent_dirs))
@@ -178,6 +185,16 @@ impl MockDaemon {
         self.state.inner.lock().expect("poisoned").inputs.clone()
     }
 
+    /// Every ACP prompt this daemon received, oldest first.
+    pub fn structured_prompts(&self) -> Vec<(Uuid, StructuredPromptRequest)> {
+        self.state
+            .inner
+            .lock()
+            .expect("poisoned")
+            .structured_prompts
+            .clone()
+    }
+
     pub fn session_count(&self) -> usize {
         self.state.inner.lock().expect("poisoned").sessions.len()
     }
@@ -266,6 +283,26 @@ async fn send_input(
     StatusCode::NO_CONTENT.into_response()
 }
 
+async fn structured_prompt(
+    State(s): State<AppState>,
+    Path(id): Path<Uuid>,
+    Json(req): Json<StructuredPromptRequest>,
+) -> Response {
+    if let Some(r) = forced(&s) {
+        return r;
+    }
+    let mut guard = s.inner.lock().expect("poisoned");
+    if !guard.sessions.iter().any(|x| x.id == id) {
+        return (
+            StatusCode::NOT_FOUND,
+            Json(ApiError::new("not_found", "no such session on this daemon")),
+        )
+            .into_response();
+    }
+    guard.structured_prompts.push((id, req));
+    StatusCode::NO_CONTENT.into_response()
+}
+
 async fn daemon_info(State(s): State<AppState>) -> Response {
     if let Some(r) = forced(&s) {
         return r;

crates/maestro-tui/src/palette.rs

@@ -82,7 +82,7 @@ impl Surface {
     pub fn activity(&self, state: ActivityState) -> Color {
         match state {
             ActivityState::Active => self.active,
-            ActivityState::Idle => self.idle,
+            ActivityState::Idle | ActivityState::Starting => self.idle,
             ActivityState::AwaitingInput => self.awaiting,
             ActivityState::Error => self.error,
         }
@@ -928,9 +928,10 @@ pub fn contrast_ratio(a: Color, b: Color) -> Option<f64> {
 mod tests {
     use super::*;
 
-    const STATES: [ActivityState; 4] = [
+    const STATES: [ActivityState; 5] = [
         ActivityState::Active,
         ActivityState::Idle,
+        ActivityState::Starting,
         ActivityState::AwaitingInput,
         ActivityState::Error,
     ];

crates/maestro-tui/src/sidebar.rs

@@ -979,6 +979,7 @@ mod tests {
         for state in [
             ActivityState::Active,
             ActivityState::Idle,
+            ActivityState::Starting,
             ActivityState::AwaitingInput,
             ActivityState::Error,
         ] {
@@ -1009,6 +1010,7 @@ mod tests {
         for state in [
             ActivityState::Active,
             ActivityState::Idle,
+            ActivityState::Starting,
             ActivityState::AwaitingInput,
             ActivityState::Error,
         ] {

docs/SIDEBAR.md

@@ -160,6 +160,7 @@ The state word is never spelled out — the colour carries it.
 | ---------------- | --------- | ---------------- |
 | `Active`         | `--live`  | `active`         |
 | `Idle`           | `--muted` | `idle`           |
+| `Starting`       | `--muted` | `idle`           |
 | `AwaitingInput`  | `--warn`  | `awaiting`       |
 | `Error`          | `--danger`| `error`          |
 

docs/STRUCTURED-VIEW.md

@@ -190,9 +190,16 @@ choices, not daemon ones.
   from the transcript; the TUI may show the current plan in its status line,
   while the web client deliberately has no stats or plan rail.
 - The web client groups two or more tool rows after the same `User` row into
-  one collapsed turn activity block. Opening it reveals independently
+  one collapsed turn activity block. `AgentText` and `AgentThought` rows that
-  expandable tool calls, including any raw command, input, output, and diff
+  appear *between* tool rows in the same turn are absorbed into the group
-  content the adapter supplied.
+  (intermediate narration); the last `AgentText` with no subsequent tool stays
+  outside as the prominent final answer. While a turn is still active
+  (responding or thinking), the most recent intermediate `AgentText` or
+  `AgentThought` in the group is kept outside as visible narration — replaced
+  by the next text row when one arrives, and absorbed into the group when the
+  turn ends. The header still reads "N tool calls" (counting only tool rows).
+  Opening the group reveals tools and intermediate text in chronological
+  order, with the text rendered in a subdued style.
 - The web client's user, agent, thought, tool-detail, and notice text blocks
   copy their complete source text when clicked or keyboard-activated.
 - The web client consumes `available_commands_update` notices as the live
@@ -346,11 +353,15 @@ thing a callback can be attributed to, so at most one turn may ever be
 in flight, and a cancelled turn must fully settle before the next prompt is
 allowed to claim the daemon's idea of "the active turn."
 
-- A prompt is appended as a durable `User` row before it claims the turn and
+- Web clients may collect a visible FIFO of operator messages while a turn is
+  active. They submit each queued message only after the projected turn becomes
+  idle; the queue is client-local and unsent messages do not survive a reload.
+- A submitted prompt is appended as a durable `User` row before it claims the turn and
   dispatches to ACP, so the transcript never depends on an adapter echoing the
   operator's input. If that append fails, the prompt is not dispatched. While a
   turn is active, a second prompt gets `409 turn_in_flight` rather than
-  queuing — one active turn per session, never a hidden queue of prompts.
+  queuing in the daemon — one active turn per session, never a hidden
+  server-side queue of prompts.
 - Cancel sends `session/cancel`, clears any pending approval as `Cancelled`,
   and ends the turn's client-visible lifecycle immediately. If the cancelled
   turn was still *dispatched* to ACP (waiting on its response), the daemon

web/src/catalog.ts

@@ -663,8 +663,9 @@ export function renderSidebar(store: CatalogStore, opts: SidebarOptions = {}): S
     applyNav();
   };
 
-  // Hover previews the row under the pointer (docs/PREVIEW.md). Touch is left
+  // Pointer hover previews only while Ctrl is held — plain hover was too
-  // out: there is no hover there, and a tap already opens the session.
+  // disruptive when sweeping the sidebar. Keyboard walk (j/k) still previews
+  // unconditionally via applyNav.
   let hovered: string | null = null;
   const setHovered = (id: string | null) => {
     if (hovered === id) return;
@@ -672,7 +673,7 @@ export function renderSidebar(store: CatalogStore, opts: SidebarOptions = {}): S
     opts.onPreview?.(id);
   };
   treeHost.addEventListener("pointerover", (e) => {
-    if (e.pointerType === "touch") return;
+    if (e.pointerType === "touch" || !e.ctrlKey) return;
     const row = (e.target as HTMLElement | null)?.closest<HTMLElement>(".tree-leaf");
     setHovered(row?.dataset.sessionId ?? null);
   });

web/src/sidebarNav.test.ts

@@ -182,26 +182,32 @@ describe("sidebar preview requests (docs/PREVIEW.md)", () => {
     expect(seen.at(-1)).toBe(null);
   });
 
-  it("asks for a preview of the hovered card, and clears it on the way out", () => {
+  it("ctrl+hover previews a card, plain hover does not", () => {
     const seen: (string | null)[] = [];
     const { el } = twoFolders({ onPreview: (id) => seen.push(id) });
     const card = el.querySelectorAll<HTMLElement>(".tree-leaf")[0];
 
+    // Plain hover — no preview.
     card.dispatchEvent(new PointerEvent("pointerover", { bubbles: true, pointerType: "mouse" }));
+    expect(seen).toEqual([]);
+
+    // Ctrl+hover — preview fires.
+    card.dispatchEvent(new PointerEvent("pointerover", { bubbles: true, pointerType: "mouse", ctrlKey: true }));
     expect(seen).toEqual([A]);
-    // Moving within the same card is not a new preview.
+
-    card.dispatchEvent(new PointerEvent("pointerover", { bubbles: true, pointerType: "mouse" }));
+    // Deduplicated while still on the same card.
+    card.dispatchEvent(new PointerEvent("pointerover", { bubbles: true, pointerType: "mouse", ctrlKey: true }));
     expect(seen).toHaveLength(1);
 
     tree(el).dispatchEvent(new PointerEvent("pointerleave", { pointerType: "mouse" }));
     expect(seen.at(-1)).toBe(null);
   });
 
-  it("ignores touch, where a tap already opens the session", () => {
+  it("ignores touch even with ctrl", () => {
     const seen: (string | null)[] = [];
     const { el } = twoFolders({ onPreview: (id) => seen.push(id) });
     const card = el.querySelectorAll<HTMLElement>(".tree-leaf")[0];
-    card.dispatchEvent(new PointerEvent("pointerover", { bubbles: true, pointerType: "touch" }));
+    card.dispatchEvent(new PointerEvent("pointerover", { bubbles: true, pointerType: "touch", ctrlKey: true }));
     expect(seen).toEqual([]);
   });
 });

web/src/spawnForm.ts

@@ -11,7 +11,7 @@ import { attachDirAutocomplete } from "./dirAutocomplete.js";
 import { parentDir } from "./paths.js";
 import { filterProjects, groupProjects, isStale, sortProjects } from "./projectList.js";
 import type { ProjectGroup } from "./projectList.js";
-import { splitCommand } from "./toolIcon.js";
+import { splitCommand, toolIconSvg, TOOL_LABELS } from "./toolIcon.js";
 import { abbreviateCwd } from "./types.js";
 import type { BranchInfo, CreateSessionRequest, Project, Session, SpawnPreset } from "./types.js";
 
@@ -140,6 +140,12 @@ export function createSpawnForm(opts: SpawnFormOptions): SpawnFormHandle {
   const form = document.createElement("form");
   form.className = "spawn-form";
   form.innerHTML = `
+    <div class="field">
+      <span class="field-label">Harness</span>
+      <div class="harness-grid cmd-tiles"></div>
+      <input class="raw-input cmd-raw" name="command_raw" type="text" hidden
+             placeholder="bash -l" autocomplete="off" />
+    </div>
     <div class="field">
       <span class="field-label">Project</span>
       <input class="raw-input project-filter" type="text" placeholder="Filter projects…"
@@ -151,12 +157,6 @@ export function createSpawnForm(opts: SpawnFormOptions): SpawnFormHandle {
                placeholder="/home/user/project" inputmode="text" autocomplete="off" />
       </div>
     </div>
-    <div class="field">
-      <span class="field-label">Command</span>
-      <div class="tile-row cmd-tiles"></div>
-      <input class="raw-input cmd-raw" name="command_raw" type="text" hidden
-             placeholder="bash -l" autocomplete="off" />
-    </div>
     <div class="advanced">
       <button type="button" class="tree-folder-header wt-toggle" aria-expanded="false">
         <span class="chevron">▾</span>
@@ -348,37 +348,69 @@ export function createSpawnForm(opts: SpawnFormOptions): SpawnFormHandle {
       command = preset!.command;
     }
     updateStructuredAvailability();
-    for (const tile of cmdTiles.querySelectorAll(".tile")) {
+    for (const card of cmdTiles.querySelectorAll(".harness-card")) {
-      tile.classList.toggle("is-active", (tile as HTMLElement).dataset.id === id);
+      card.classList.toggle("is-active", (card as HTMLElement).dataset.id === id);
     }
     emit();
   }
 
-  /** Re-highlight the operator's already-picked tile after `renderCommandTiles`
+  /** Re-highlight the operator's already-picked card after `renderCommandTiles`
-   * rebuilds the row from scratch (new tiles carry no `is-active` class) —
+   * rebuilds the grid from scratch (new cards carry no `is-active` class) —
    * without touching `command`, since that was already settled. */
   function reapplyActiveTile(): void {
-    for (const tile of cmdTiles.querySelectorAll(".tile")) {
+    for (const card of cmdTiles.querySelectorAll(".harness-card")) {
-      tile.classList.toggle("is-active", (tile as HTMLElement).dataset.id === selectedPresetId);
+      card.classList.toggle("is-active", (card as HTMLElement).dataset.id === selectedPresetId);
     }
   }
 
+  /** Resolve a preset id to a tool icon id. The preset's command is the
+   * source of truth — `splitCommand` extracts the tool the same way the
+   * sidebar does. For the "Custom…" preset (empty command) there is no
+   * tool to show, and a terminal prompt stands in. */
+  function presetToolId(p: SpawnPreset): string | null {
+    if (!p.command) return null;
+    return splitCommand(p.command).tool;
+  }
+
   function renderCommandTiles(): void {
     cmdTiles.replaceChildren();
     for (const p of presets) {
-      const tile = document.createElement("button");
+      const isCustom = p.command === "";
-      tile.type = "button";
+      const card = document.createElement("button");
-      tile.className = "tile";
+      card.type = "button";
-      tile.dataset.id = p.id;
+      card.className = isCustom ? "harness-card harness-custom" : "harness-card";
-      tile.innerHTML = `<span class="tile-label">${escapeHtml(p.label)}</span>`;
+      card.dataset.id = p.id;
-      tile.addEventListener("click", () => {
+      const toolId = presetToolId(p);
+      const iconHtml = isCustom ? customIcon() : toolId ? harnessIcon(toolId) : harnessIcon("shell");
+      const label = TOOL_LABELS[toolId ?? ""] ?? p.label;
+      card.innerHTML =
+        `<span class="harness-icon">${iconHtml}</span>` +
+        `<span class="harness-label">${escapeHtml(isCustom ? "Custom\u2026" : label)}</span>`;
+      card.addEventListener("click", () => {
         commandTouched = true;
         selectPreset(p.id);
       });
-      cmdTiles.appendChild(tile);
+      cmdTiles.appendChild(card);
     }
   }
 
+  /** Render a harness card icon at card size (24x24). Re-uses the SVG bodies
+   * from toolIcon.ts but at a larger viewport so the marks breathe. */
+  function harnessIcon(toolId: string): string {
+    // toolIconSvg renders at 13x13 with viewBox 0 0 16 16 — we want the
+    // same shape at 24x24 for the card context.
+    const small = toolIconSvg(toolId);
+    if (!small) return "";
+    return small
+      .replace(/width="13"/g, 'width="24"')
+      .replace(/height="13"/g, 'height="24"');
+  }
+
+  /** An ellipsis mark for the "Custom…" escape hatch. */
+  function customIcon(): string {
+    return `<svg class="tool-icon" viewBox="0 0 16 16" width="24" height="24" role="img" aria-label="Custom command"><title>Custom command</title><g fill="currentColor"><circle cx="4" cy="8" r="1.3"/><circle cx="8" cy="8" r="1.3"/><circle cx="12" cy="8" r="1.3"/></g></svg>`;
+  }
+
   // Set once the operator picks a tile or types a custom command — guards
   // `applyInitialCommand()` the same way `nameTouched` guards a late name
   // batch: a late `/api/info` resolution must never overwrite a field the
@@ -648,16 +680,13 @@ export function createSpawnForm(opts: SpawnFormOptions): SpawnFormHandle {
     box.type = "button";
     box.className = `project-box${isStale(project, new Date()) ? " is-stale" : ""}`;
     box.dataset.cwd = project.path;
-    const trees = worktreesOf(group).length;
     // The parent directory only — the last segment is the name line above it.
     // Unabbreviated beyond `~`, since the stem is what tells two projects
     // sharing a basename apart (#95).
     const parent = abbreviateCwd(parentDir(project.path), homeDir);
-    const meta = trees > 0 ? `${trees} worktree${trees === 1 ? "" : "s"}` : "";
     box.innerHTML = `
       <span class="project-name">${escapeHtml(project.name)}</span>
-      <span class="project-path">${escapeHtml(parent)}</span>
+      <span class="project-path">${escapeHtml(parent)}</span>`;
-      <span class="project-meta">${escapeHtml(meta)}</span>`;
     box.addEventListener("click", () => selectProject(group));
     return box;
   }

web/src/spawnFormEnter.test.ts

@@ -139,7 +139,7 @@ describe("spawnForm Enter-to-submit (#97)", () => {
       const form = await mount([MAESTRO]);
       box(form, MAESTRO.path).click();
       await drain();
-      form.querySelector<HTMLButtonElement>('.cmd-tiles .tile[data-id="custom"]')!.click();
+      form.querySelector<HTMLButtonElement>('.cmd-tiles .harness-card[data-id="custom"]')!.click();
       const raw = form.querySelector<HTMLInputElement>(".cmd-raw")!;
       raw.value = "bash -l";
       raw.dispatchEvent(new Event("input"));

web/src/spawnFormPreset.test.ts

@@ -63,7 +63,7 @@ describe("spawnForm preset selection vs. late /api/info (#76)", () => {
     await drain();
 
     // Fallback presets are up; the operator picks "zsh" before /api/info lands.
-    const zshTile = [...form.querySelectorAll<HTMLButtonElement>(".tile")].find(
+    const zshTile = [...form.querySelectorAll<HTMLButtonElement>(".harness-card")].find(
       (t) => t.dataset.id === "zsh",
     )!;
     zshTile.click();
@@ -88,7 +88,7 @@ describe("spawnForm preset selection vs. late /api/info (#76)", () => {
     document.body.appendChild(form);
     await drain();
 
-    const customTile = [...form.querySelectorAll<HTMLButtonElement>(".tile")].find(
+    const customTile = [...form.querySelectorAll<HTMLButtonElement>(".harness-card")].find(
       (t) => t.dataset.id === "custom",
     )!;
     customTile.click();
@@ -116,7 +116,7 @@ describe("spawnForm preset selection vs. late /api/info (#76)", () => {
 
     // Untouched: the refined preset list is still free to settle the command.
     expect(values?.command).toBe("claude");
-    const fishTile = [...form.querySelectorAll<HTMLButtonElement>(".tile")].find(
+    const fishTile = [...form.querySelectorAll<HTMLButtonElement>(".harness-card")].find(
       (t) => t.dataset.id === "fish",
     );
     expect(fishTile).toBeDefined();

web/src/spawnModal.test.ts

@@ -52,14 +52,14 @@ describe("spawn modal", () => {
     expect(host.querySelector(".form-actions .cancel")).toBeTruthy();
   });
 
-  it("opens with the project filter focused, ahead of the command tiles", async () => {
+  it("opens with the project filter focused, harness before project", async () => {
     openSpawnModal({ onSuccess: () => {} });
     await flush();
 
     const form = modal()!.querySelector("form.spawn-form")!;
     expect(document.activeElement).toBe(form.querySelector(".project-filter"));
     const fields = [...form.querySelectorAll(".field .field-label")].map((el) => el.textContent);
-    expect(fields.slice(0, 2)).toEqual(["Project", "Command"]);
+    expect(fields.slice(0, 2)).toEqual(["Harness", "Project"]);
   });
 
   it("titles a seeded open as a clone", async () => {

web/src/structured.test.ts

@@ -134,7 +134,7 @@ describe("structured connection: data flow", () => {
     } });
     input.dispatchEvent(paste);
     conn.el.querySelector("form")!.dispatchEvent(new Event("submit", { cancelable: true }));
-    await vi.waitFor(() => expect(input.disabled).toBe(false));
+    await vi.waitFor(() => expect(conn.el.textContent).toContain("Upload failed"));
     expect(input.value).toBe("Read this");
     expect(sendStructuredPrompt).not.toHaveBeenCalled();
     const remove = conn.el.querySelector<HTMLButtonElement>('[aria-label="Remove notes.txt"]')!;
@@ -413,6 +413,73 @@ describe("structured connection: data flow", () => {
     conn.dispose();
   });
 
+  it("absorbs intermediate agent text into tool group, keeps final text outside", () => {
+    const ws = new FakeSocket();
+    const conn = mount({ sockets: [ws] });
+    ws.open();
+    ws.emit({
+      type: "transcript_snapshot",
+      snapshot: {
+        cursor: 8,
+        rows: [
+          row("user:1", "user", { content: { type: "text", text: "do it" } }),
+          row("agent:1", "agent_text", { content: { type: "text", text: "Let me check" } }),
+          toolRow("tool:1", "one"),
+          toolRow("tool:2", "two"),
+          row("agent:2", "agent_text", { content: { type: "text", text: "Found issues, fixing" } }),
+          toolRow("tool:3", "three"),
+          toolRow("tool:4", "four"),
+          row("agent:3", "agent_text", { content: { type: "text", text: "All done" } }),
+        ],
+      },
+    });
+    const groups = conn.el.querySelectorAll<HTMLElement>(".st-tool-group");
+    expect(groups).toHaveLength(1);
+    // Header counts only tool rows, not intermediate text.
+    expect(groups[0].querySelector(".st-tool-group-head")!.textContent).toContain("4 tool calls");
+    // Intermediate text (agent:2) is inside the group.
+    expect(conn.el.querySelector('[data-row-id="agent:2"]')?.closest(".st-tool-group")).not.toBeNull();
+    // First text (agent:1) is outside — it precedes all tools.
+    expect(conn.el.querySelector('[data-row-id="agent:1"]')?.closest(".st-tool-group")).toBeNull();
+    // Final text (agent:3) is outside — no tool follows it.
+    expect(conn.el.querySelector('[data-row-id="agent:3"]')?.closest(".st-tool-group")).toBeNull();
+    conn.dispose();
+  });
+
+  it("keeps last intermediate text outside group while turn is active", () => {
+    const ws = new FakeSocket();
+    const conn = mount({ sockets: [ws] });
+    ws.open();
+    const respondingState: ReducedState = {
+      turn: { responding: true, thinking: false, active_tool_calls: [] },
+    };
+    ws.emit({
+      type: "transcript_snapshot",
+      snapshot: {
+        cursor: 6,
+        rows: [
+          row("user:1", "user", { content: { type: "text", text: "do it" } }),
+          toolRow("tool:1", "one"),
+          row("agent:1", "agent_text", { content: { type: "text", text: "Now fixing" } }),
+          toolRow("tool:2", "two"),
+          row("agent:2", "agent_text", { content: { type: "text", text: "Found more" } }),
+          toolRow("tool:3", "three"),
+        ],
+      },
+    });
+    ws.emit({ type: "reduced_state", state: respondingState });
+    // While the turn is active, the last intermediate text (agent:2) stays
+    // outside the collapsed group so it's visible as current narration.
+    expect(conn.el.querySelector('[data-row-id="agent:2"]')?.closest(".st-tool-group")).toBeNull();
+    // Earlier intermediate text (agent:1) is still inside the group.
+    expect(conn.el.querySelector('[data-row-id="agent:1"]')?.closest(".st-tool-group")).not.toBeNull();
+    // When the turn ends, all intermediate text is absorbed.
+    ws.emit({ type: "reduced_state", state: idleState });
+    expect(conn.el.querySelector('[data-row-id="agent:2"]')?.closest(".st-tool-group")).not.toBeNull();
+    expect(conn.el.querySelector('[data-row-id="agent:1"]')?.closest(".st-tool-group")).not.toBeNull();
+    conn.dispose();
+  });
+
   it("keeps an expanded running tool open without emitting a click when patched", () => {
     const ws = new FakeSocket();
     const conn = mount({ sockets: [ws] });
@@ -660,7 +727,7 @@ describe("structured connection: turn/composer gating", () => {
     conn.dispose();
   });
 
-  it("disables the composer while a turn is active and re-enables when idle", () => {
+  it("keeps the composer available while a turn is active", () => {
     const ws = new FakeSocket();
     const conn = mount({ sockets: [ws] });
     ws.open();
@@ -668,13 +735,13 @@ describe("structured connection: turn/composer gating", () => {
     const input = conn.el.querySelector(".structured-input") as HTMLTextAreaElement;
     const cancel = conn.el.querySelector(".structured-cancel") as HTMLButtonElement;
     ws.emit({ type: "reduced_state", state: { turn: { responding: true, thinking: false, active_tool_calls: [] } } });
-    expect(input.disabled).toBe(true);
+    expect(input.disabled).toBe(false);
     expect(cancel.hidden).toBe(false);
-    expect((conn.el.querySelector(".structured-send") as HTMLButtonElement).hidden).toBe(true);
+    expect((conn.el.querySelector(".structured-send span") as HTMLElement).textContent).toBe("Send");
     ws.emit({ type: "reduced_state", state: idleState });
     expect(input.disabled).toBe(false);
     expect(cancel.hidden).toBe(true);
-    expect((conn.el.querySelector(".structured-send") as HTMLButtonElement).hidden).toBe(false);
+    expect((conn.el.querySelector(".structured-send span") as HTMLElement).textContent).toBe("Send");
     conn.dispose();
   });
 
@@ -737,7 +804,7 @@ describe("structured connection: turn/composer gating", () => {
     conn.dispose();
   });
 
-  it("disables immediately and dispatches only once before begin-turn is projected", () => {
+  it("queues a second message before begin-turn is projected", () => {
     vi.mocked(sendStructuredPrompt).mockImplementationOnce(() => new Promise(() => {}));
     const ws = new FakeSocket();
     const conn = mount({ sockets: [ws] });
@@ -750,12 +817,43 @@ describe("structured connection: turn/composer gating", () => {
     input.value = "only once";
 
     form.dispatchEvent(new SubmitEvent("submit", { bubbles: true, cancelable: true }));
+    input.value = "queued next";
     form.dispatchEvent(new SubmitEvent("submit", { bubbles: true, cancelable: true }));
 
-    expect(input.disabled).toBe(true);
+    expect(input.disabled).toBe(false);
-    expect(send.disabled).toBe(true);
+    expect(send.disabled).toBe(false);
     expect(sendStructuredPrompt).toHaveBeenCalledTimes(1);
     expect(sendStructuredPrompt).toHaveBeenCalledWith("s1", "only once");
+    expect(conn.el.querySelector(".structured-queue")?.textContent).toBe("1 message queued");
+    conn.dispose();
+  });
+
+  it("dispatches queued messages in order as turns become idle", async () => {
+    const ws = new FakeSocket();
+    const conn = mount({ sockets: [ws] });
+    ws.open();
+    ws.emit({ type: "reduced_state", state: idleState });
+    const input = conn.el.querySelector(".structured-input") as HTMLTextAreaElement;
+    const submit = (text: string) => {
+      input.value = text;
+      input.dispatchEvent(new KeyboardEvent("keydown", { key: "Enter", bubbles: true, cancelable: true }));
+    };
+
+    submit("first");
+    ws.emit({ type: "reduced_state", state: { turn: { responding: true, thinking: false, active_tool_calls: [] } } });
+    submit("second");
+    submit("third");
+    expect(sendStructuredPrompt).toHaveBeenCalledTimes(1);
+    expect(conn.el.querySelector(".structured-queue")?.textContent).toBe("2 messages queued");
+
+    await Promise.resolve().then(() => Promise.resolve());
+    ws.emit({ type: "reduced_state", state: idleState });
+    expect(sendStructuredPrompt).toHaveBeenNthCalledWith(2, "s1", "second");
+    ws.emit({ type: "reduced_state", state: { turn: { responding: true, thinking: false, active_tool_calls: [] } } });
+    await Promise.resolve().then(() => Promise.resolve());
+    ws.emit({ type: "reduced_state", state: idleState });
+    expect(sendStructuredPrompt).toHaveBeenNthCalledWith(3, "s1", "third");
+    expect((conn.el.querySelector(".structured-queue") as HTMLElement).hidden).toBe(true);
     conn.dispose();
   });
 
@@ -807,7 +905,7 @@ describe("structured connection: turn/composer gating", () => {
 
     expect(sendStructuredPrompt).toHaveBeenCalledTimes(2);
     expect(input.value).toBe("");
-    expect(input.disabled).toBe(true);
+    expect(input.disabled).toBe(false);
     expect(conn.el.textContent).not.toContain("stale failure");
     conn.dispose();
   });
@@ -869,7 +967,7 @@ describe("structured connection: approvals", () => {
     conn.dispose();
   });
 
-  it("removes the buttons once the approval resolves, even with no accompanying transcript delta", () => {
+  it("hides a standalone resolved approval entirely when no tool group absorbs it", () => {
     const ws = new FakeSocket();
     const conn = mount({ sockets: [ws] });
     ws.open();
@@ -885,7 +983,68 @@ describe("structured connection: approvals", () => {
     // Resolved on another client: state clears with no transcript delta at all.
     ws.emit({ type: "reduced_state", state: idleState });
     expect(conn.el.querySelector(".st-approval-acts")).toBeNull();
-    expect(conn.el.querySelector(".st-approval-resolved")).not.toBeNull();
+    // Standalone resolved approval is hidden — no card, no compact line.
+    expect(conn.el.querySelector(".st-row-approval")).toBeNull();
+    conn.dispose();
+  });
+
+  it("absorbs a resolved approval into the tool group as a compact line", () => {
+    const ws = new FakeSocket();
+    const conn = mount({ sockets: [ws] });
+    ws.open();
+    ws.emit({
+      type: "transcript_snapshot",
+      snapshot: {
+        cursor: 0,
+        rows: [
+          row("user:1", "user", { content: { text: "go" } }),
+          toolRow("tool:1", "first"),
+          row("approval:1", "approval", { toolCall: { title: "Write file.ts" }, options: allApprovalOptions }),
+          toolRow("tool:2", "second"),
+        ],
+      },
+    });
+    ws.emit({ type: "reduced_state", state: idleState });
+    // 2+ tools in the turn → tool group exists; resolved approval is inside it.
+    const group = conn.el.querySelector(".st-tool-group");
+    expect(group).not.toBeNull();
+    const compact = group!.querySelector(".st-approval-compact");
+    expect(compact).not.toBeNull();
+    expect(compact!.textContent).toContain("Write file.ts");
+    expect(compact!.textContent).toContain("approved");
+    // No full-card approval anywhere on the transcript.
+    expect(conn.el.querySelector(".st-approval")).toBeNull();
+    conn.dispose();
+  });
+
+  it("keeps a pending approval standalone even when a tool group exists in the same turn", () => {
+    const ws = new FakeSocket();
+    const conn = mount({ sockets: [ws] });
+    ws.open();
+    ws.emit({
+      type: "transcript_snapshot",
+      snapshot: {
+        cursor: 0,
+        rows: [
+          row("user:1", "user", { content: { text: "go" } }),
+          toolRow("tool:1", "first"),
+          row("approval:1", "approval", { toolCall: { title: "Write file.ts" }, options: allApprovalOptions }),
+          toolRow("tool:2", "second"),
+        ],
+      },
+    });
+    ws.emit({
+      type: "reduced_state",
+      state: { ...idleState, pending_approval: { nonce: "n1", request: { sessionId: "s1", toolCall: {}, options: allApprovalOptions } } },
+    });
+    // Pending approval stays outside the tool group as a full card.
+    const approvalCard = conn.el.querySelector(".st-approval");
+    expect(approvalCard).not.toBeNull();
+    expect(conn.el.querySelectorAll(".st-approval-acts button").length).toBeGreaterThan(0);
+    // It should not be inside the tool group.
+    const group = conn.el.querySelector(".st-tool-group");
+    expect(group).not.toBeNull();
+    expect(group!.querySelector(".st-approval")).toBeNull();
     conn.dispose();
   });
 
@@ -1126,7 +1285,7 @@ describe("structured connection: reconnection/error/loading", () => {
     second.open();
     second.emit({ type: "transcript_snapshot", snapshot: { cursor: 0, rows: [] } });
     second.emit({ type: "reduced_state", state: idleState });
-    expect(input.disabled).toBe(true);
+    expect(input.disabled).toBe(false);
 
     second.emit({ type: "reduced_state", state: { turn: { responding: true, thinking: false, active_tool_calls: [] } } });
     second.emit({ type: "reduced_state", state: idleState });
@@ -1178,12 +1337,12 @@ describe("structured connection: reconnection/error/loading", () => {
     second.open();
     second.emit({ type: "transcript_snapshot", snapshot: { cursor: 0, rows: [] } });
     second.emit({ type: "reduced_state", state: idleState });
-    expect(input.disabled).toBe(true);
+    expect(input.disabled).toBe(false);
 
     accept();
     await Promise.resolve().then(() => Promise.resolve());
 
-    expect(input.disabled).toBe(true);
+    expect(input.disabled).toBe(false);
     expect(second.closed).toBe(true);
 
     third.open();
@@ -1584,7 +1743,7 @@ describe("structured connection: pane lifecycle", () => {
     conn.dispose();
   });
 
-  it("focusTerminal focuses the composer only when it is enabled", () => {
+  it("focusTerminal keeps the composer reachable during an active turn", () => {
     const ws = new FakeSocket();
     const conn = mount({ sockets: [ws] });
     ws.open();
@@ -1592,7 +1751,7 @@ describe("structured connection: pane lifecycle", () => {
     ws.emit({ type: "reduced_state", state: { turn: { responding: true, thinking: false, active_tool_calls: [] } } });
     conn.focusTerminal();
     const input = conn.el.querySelector(".structured-input") as HTMLTextAreaElement;
-    expect(document.activeElement).not.toBe(input);
+    expect(document.activeElement).toBe(input);
     ws.emit({ type: "reduced_state", state: idleState });
     conn.focusTerminal();
     expect(document.activeElement).toBe(input);

web/src/structured.ts

@@ -85,10 +85,10 @@ export function createStructuredConnection(
       <div class="structured-main">
         <div class="structured-scroll">
           <div class="structured-rows"></div>
-        </div>
+          <div class="structured-activity" role="status" aria-live="polite" hidden>
-        <div class="structured-activity" role="status" aria-live="polite" hidden>
+            <span class="structured-activity-pulse" aria-hidden="true"></span>
-          <span class="structured-activity-pulse" aria-hidden="true"></span>
+            <span class="structured-activity-text">Thinking</span>
-          <span class="structured-activity-text">Thinking</span>
+          </div>
         </div>
         <form class="structured-composer">
           <button type="button" class="btn btn-ghost btn-icon structured-attach" aria-label="Attach files" title="Attach files (up to 20 MiB each)">
@@ -113,7 +113,11 @@ export function createStructuredConnection(
           <button type="submit" class="btn btn-primary structured-send"><span>Send</span>
             <svg viewBox="0 0 20 20" aria-hidden="true"><path d="m7 5 5 5-5 5M12 10H3"/></svg>
           </button>
-          <button type="button" class="btn structured-cancel" hidden>Cancel turn</button>
+          <button type="button" class="btn btn-icon structured-cancel" hidden aria-label="Cancel turn" title="Cancel turn">
+            <svg class="structured-cancel-spinner" viewBox="0 0 24 24" aria-hidden="true"><circle cx="12" cy="12" r="10" fill="none" stroke="currentColor" stroke-width="2" stroke-dasharray="50 14" stroke-linecap="round"/></svg>
+            <svg class="structured-cancel-stop" viewBox="0 0 24 24" aria-hidden="true"><rect x="6" y="6" width="12" height="12" rx="2" fill="currentColor"/></svg>
+          </button>
+          <span class="structured-queue" role="status" aria-live="polite" hidden></span>
         </form>
       </div>
     </div>
@@ -133,11 +137,14 @@ export function createStructuredConnection(
   const commandMenu = el.querySelector(".structured-command-menu") as HTMLDivElement;
   const input = el.querySelector(".structured-input") as HTMLTextAreaElement;
   const sendBtn = el.querySelector(".structured-send") as HTMLButtonElement;
+  const sendLabel = sendBtn.querySelector("span") as HTMLSpanElement;
   const cancelBtn = el.querySelector(".structured-cancel") as HTMLButtonElement;
+  const queueEl = el.querySelector(".structured-queue") as HTMLSpanElement;
   const attachBtn = el.querySelector(".structured-attach") as HTMLButtonElement;
   const fileInput = el.querySelector(".structured-file-input") as HTMLInputElement;
   const attachmentEl = el.querySelector(".structured-attachments") as HTMLDivElement;
   type Attachment = { file: File; path?: string };
+  type QueuedPrompt = { text: string; attachments: Attachment[] };
   let attachments: Attachment[] = [];
   let uploading = false;
   let pasteCount = 0;
@@ -155,7 +162,7 @@ export function createStructuredConnection(
       remove.type = "button";
       remove.textContent = "×";
       remove.setAttribute("aria-label", `Remove ${attachment.file.name}`);
-      remove.disabled = input.disabled;
+      remove.disabled = uploading;
       remove.addEventListener("click", () => {
         attachments = attachments.filter((item) => item !== attachment);
         renderAttachments();
@@ -166,7 +173,7 @@ export function createStructuredConnection(
   }
 
   function addFiles(files: File[]): void {
-    if (input.disabled || disposed) return;
+    if (uploading || disposed) return;
     for (const file of files) {
       if (file.size > 20 * 1024 * 1024) {
         showError(`${file.name} exceeds 20 MiB. Choose a smaller file.`);
@@ -193,7 +200,7 @@ export function createStructuredConnection(
   });
   input.addEventListener("paste", (event) => {
     const clipboard = event.clipboardData;
-    if (!clipboard || input.disabled) return;
+    if (!clipboard || uploading) return;
     if (clipboard.files.length) {
       event.preventDefault();
       addFiles(Array.from(clipboard.files));
@@ -244,6 +251,10 @@ export function createStructuredConnection(
   let disposed = false;
   let optimisticTurnStartedAt: number | null = null;
   let activityTimer: number | null = null;
+  const promptQueue: QueuedPrompt[] = [];
+  let promptRequestPending = false;
+  /** Server path → object URL for uploaded images, so user bubbles can show previews. */
+  const imageObjectUrls = new Map<string, string>();
 
   // Within 64px, wheel and touch imprecision should still count as following.
   const FOLLOW_BOTTOM_THRESHOLD_PX = 64;
@@ -374,6 +385,9 @@ export function createStructuredConnection(
     }
   }
 
+  /** Pattern matching `Attached file "name": "path"` references appended by dispatchPrompt. */
+  const attachedFileRe = /Attached file "(?:[^"\\]|\\.)*": "((?:[^"\\]|\\.)*)"/g;
+
   function buildRowElement(row: TranscriptRow): HTMLElement | null {
     const el = buildTranscriptRow(
       row,
@@ -390,20 +404,112 @@ export function createStructuredConnection(
     if (el.querySelector(".st-tool-head")?.getAttribute("aria-expanded") !== "true") {
       expandedRowIds.delete(row.id);
     }
+    // Inject image previews into user message bubbles and strip the path text.
+    if (row.kind === "user" && imageObjectUrls.size > 0) {
+      const data = row.data as { content?: { type: string; text?: string } } | undefined;
+      const text = data?.content?.type === "text" ? data.content.text ?? "" : "";
+      const body = el.querySelector(".st-body");
+      if (body && text) {
+        const images: string[] = [];
+        attachedFileRe.lastIndex = 0;
+        let match: RegExpExecArray | null;
+        while ((match = attachedFileRe.exec(text)) !== null) {
+          const serverPath = JSON.parse(`"${match[1]}"`);
+          const objectUrl = imageObjectUrls.get(serverPath);
+          if (objectUrl) images.push(objectUrl);
+        }
+        if (images.length > 0) {
+          // Strip attachment reference lines from the displayed text.
+          const userText = body.querySelector(".st-user-text");
+          if (userText) {
+            const cleaned = text.replace(/\n\nAttached file "[^"]*": "[^"]*"/g, "").trim();
+            userText.textContent = cleaned;
+            if (!cleaned) userText.remove();
+          }
+          for (const src of images) {
+            const img = document.createElement("img");
+            img.className = "st-user-image";
+            img.src = src;
+            img.alt = "Uploaded image";
+            img.loading = "lazy";
+            body.appendChild(img);
+          }
+        }
+      }
+    }
     return el;
   }
 
-  function toolGroupsByTurn(): Map<string, TranscriptRow[]> {
+  /** Group tool rows (and intermediate agent text / resolved approvals between
-    const groups = new Map<string, TranscriptRow[]>();
+   *  them) by turn.  An agent_text/agent_thought row is "intermediate" when a
+   *  tool row follows it in the same turn — it gets absorbed into the group so
+   *  the collapsed block preserves chronological order.  Resolved approval rows
+   *  (not the currently pending one) are absorbed the same way.  The *last*
+   *  agent text with no subsequent tool stays standalone (the prominent final
+   *  answer).  Returns groups keyed by `turn:<userId>`, each with `toolCount`
+   *  (for the header label) and `rows` (tools + intermediate text/approvals,
+   *  in order). */
+  function activityGroupsByTurn(): Map<string, { toolCount: number; rows: TranscriptRow[] }> {
+    // First: count tools per turn to know which turns qualify for grouping.
+    const toolCounts = new Map<string, number>();
     let turnId = "before-first-message";
     for (const row of rows) {
       if (row.kind === "user") turnId = row.id;
       if (row.kind !== "tool_call" && row.kind !== "tool_diff") continue;
-      const id = `turn:${turnId}`;
+      const gid = `turn:${turnId}`;
-      const group = groups.get(id) ?? [];
+      toolCounts.set(gid, (toolCounts.get(gid) ?? 0) + 1);
-      group.push(row);
-      groups.set(id, group);
     }
+    // Second: build groups with interleaved text for turns with 2+ tools.
+    const groups = new Map<string, { toolCount: number; rows: TranscriptRow[] }>();
+    turnId = "before-first-message";
+    // Pending rows that might be intermediate (not yet confirmed by a
+    // following tool). If no tool follows, they stay standalone.
+    let pending: TranscriptRow[] = [];
+    let currentGid = `turn:${turnId}`;
+    for (const row of rows) {
+      if (row.kind === "user") {
+        turnId = row.id;
+        currentGid = `turn:${turnId}`;
+        pending = [];
+        continue;
+      }
+      const count = toolCounts.get(currentGid) ?? 0;
+      if (count < 2) continue;
+      const isIntermediateText = row.kind === "agent_text" || row.kind === "agent_thought";
+      const isResolvedApproval = row.kind === "approval" && row.id !== pendingApprovalRowId;
+      if (isIntermediateText || isResolvedApproval) {
+        pending.push(row);
+        continue;
+      }
+      if (row.kind === "tool_call" || row.kind === "tool_diff") {
+        const group = groups.get(currentGid) ?? { toolCount: count, rows: [] };
+        // Flush any pending rows — a tool follows, so they're intermediate.
+        group.rows.push(...pending);
+        pending = [];
+        group.rows.push(row);
+        groups.set(currentGid, group);
+      }
+    }
+    // pending at end of a turn = final text/approvals, stays outside (not flushed).
+
+    // While the turn is still active, keep the last intermediate text/thought
+    // row outside the collapsed group so it's visible as the agent's current
+    // narration. It gets absorbed on the next rebuild once newer content
+    // arrives or the turn ends.
+    const turnActive = state.turn.responding || state.turn.thinking;
+    if (turnActive) {
+      const lastGroup = groups.get(currentGid);
+      if (lastGroup) {
+        for (let i = lastGroup.rows.length - 1; i >= 0; i--) {
+          const kind = lastGroup.rows[i].kind;
+          if (kind === "agent_text" || kind === "agent_thought") {
+            lastGroup.rows.splice(i, 1);
+            break;
+          }
+        }
+      }
+    }
+
     return groups;
   }
 
@@ -413,9 +519,9 @@ export function createStructuredConnection(
     const focusedGroupId = active?.closest<HTMLElement>("[data-tool-group-id]")?.dataset.toolGroupId;
     const restoreToolFocus = active?.classList.contains("st-tool-head") ?? false;
     const restoreGroupFocus = active?.classList.contains("st-tool-group-head") ?? false;
-    const groups = toolGroupsByTurn();
+    const groups = activityGroupsByTurn();
     const groupedRowIds = new Set<string>();
-    const liveGroupIds = new Set([...groups].filter(([, tools]) => tools.length > 1).map(([id]) => id));
+    const liveGroupIds = new Set([...groups.keys()]);
     for (const id of expandedGroupIds) if (!liveGroupIds.has(id)) expandedGroupIds.delete(id);
 
     rowEls.clear();
@@ -425,34 +531,40 @@ export function createStructuredConnection(
     for (const row of rows) {
       if (row.kind === "user") turnId = row.id;
       const groupId = `turn:${turnId}`;
-      const groupRows = groups.get(groupId) ?? [];
+      const group = groups.get(groupId);
-      if ((row.kind === "tool_call" || row.kind === "tool_diff") && groupRows.length > 1) {
+      if (group && groupedRowIds.has(row.id)) continue;
-        if (groupedRowIds.has(row.id)) continue;
+      if (group && (row.kind === "tool_call" || row.kind === "tool_diff") && !groupedRowIds.has(row.id)) {
-        const toolEls = groupRows.flatMap((toolRow) => {
+        // First ungrouped tool in this turn — render the whole activity group.
-          groupedRowIds.add(toolRow.id);
+        const memberEls = group.rows.flatMap((memberRow) => {
-          const toolEl = buildRowElement(toolRow);
+          groupedRowIds.add(memberRow.id);
-          if (!toolEl) return [];
+          const memberEl = buildRowElement(memberRow);
-          rowEls.set(toolRow.id, toolEl);
+          if (!memberEl) return [];
-          return [toolEl];
+          rowEls.set(memberRow.id, memberEl);
+          return [memberEl];
         });
         const groupEl = buildToolGroup(
           groupId,
-          groupRows,
+          group.rows,
-          toolEls,
+          memberEls,
           expandedGroupIds.has(groupId),
           (expanded) => {
             if (expanded) expandedGroupIds.add(groupId);
             else expandedGroupIds.delete(groupId);
             settleDisclosureLayout();
           },
+          group.toolCount,
         );
-        if (groupRows.some((toolRow) => enteringRowIds.has(toolRow.id))) {
+        if (group.rows.some((r) => enteringRowIds.has(r.id))) {
           groupEl.classList.add("st-row-enter");
         }
         groupEls.set(groupId, groupEl);
         children.push(groupEl);
         continue;
       }
+      // Resolved approvals not absorbed into a tool group are hidden — the
+      // tool row itself already identifies the action, so a standalone
+      // "answered" card adds nothing.  Pending approvals always render.
+      if (row.kind === "approval" && row.id !== pendingApprovalRowId) continue;
       const rowEl = buildRowElement(row);
       if (!rowEl) continue;
       rowEls.set(row.id, rowEl);
@@ -504,6 +616,19 @@ export function createStructuredConnection(
           rows.push(delta.row);
         } else {
           rows[i] = delta.row;
+          // Surgical DOM swap: replace just this row's element instead of
+          // tearing down and rebuilding the entire transcript, which causes
+          // visible flashing and breaks text selection.
+          const oldEl = rowEls.get(delta.row.id);
+          if (oldEl) {
+            const newEl = buildRowElement(delta.row);
+            if (newEl) {
+              oldEl.replaceWith(newEl);
+              rowEls.set(delta.row.id, newEl);
+            }
+            syncAvailableCommands();
+            return;
+          }
         }
       } else {
         const i = rowIndex.get(delta.id);
@@ -606,16 +731,19 @@ export function createStructuredConnection(
   }
 
   function renderComposerState(): void {
-    const active = uploading || state.turn.responding || state.turn.thinking || awaitingBeginGeneration !== null;
     const projectedActive = state.turn.responding || state.turn.thinking;
-    input.disabled = active;
+    input.disabled = false;
-    attachBtn.disabled = active;
+    attachBtn.disabled = uploading;
-    fileInput.disabled = active;
+    fileInput.disabled = uploading;
     renderAttachments();
-    sendBtn.disabled = active;
+    sendBtn.disabled = false;
-    sendBtn.hidden = projectedActive;
+    sendBtn.hidden = false;
+    sendLabel.textContent = "Send";
     cancelBtn.hidden = !projectedActive;
-    if (active) closeCommandMenu();
+    queueEl.hidden = promptQueue.length === 0;
+    queueEl.textContent = promptQueue.length === 1
+      ? "1 message queued"
+      : `${promptQueue.length} messages queued`;
     renderActivity();
   }
 
@@ -627,6 +755,7 @@ export function createStructuredConnection(
 
   function renderActivity(): void {
     const active = state.turn.responding || state.turn.thinking || awaitingBeginGeneration !== null;
+    const wasHidden = activityEl.hidden;
     activityEl.hidden = !active;
     if (!active) {
       optimisticTurnStartedAt = null;
@@ -649,6 +778,11 @@ export function createStructuredConnection(
     }
     activityText.textContent = parts.join(" · ");
     if (activityTimer === null) activityTimer = window.setInterval(renderActivity, 1_000);
+    // Activity lives inside the scroll area; nudge scroll when it first appears.
+    if (wasHidden && followingBottom) {
+      beginTranscriptLayout(true);
+      finishTranscriptLayout();
+    }
   }
 
   function reconcileAwaitingBegin(): void {
@@ -664,19 +798,22 @@ export function createStructuredConnection(
   }
 
   function applyState(next: ReducedState, connectionGeneration: number): void {
+    const wasTurnActive = state.turn.responding || state.turn.thinking;
     state = next;
     stateSocketGeneration = connectionGeneration;
     reconcileAwaitingBegin();
+    const isTurnActive = state.turn.responding || state.turn.thinking;
     const newPendingId = state.pending_approval ? lastRowIdOfKind("approval") : null;
-    if (newPendingId !== pendingApprovalRowId) {
+    const needsRebuild = newPendingId !== pendingApprovalRowId || wasTurnActive !== isTurnActive;
+    if (needsRebuild) {
       updateTranscriptLayout(() => {
-        const prev = pendingApprovalRowId;
         pendingApprovalRowId = newPendingId;
-        if (prev !== null || newPendingId !== null) rebuildTranscript();
+        rebuildTranscript();
       });
     }
     renderConfig();
     renderComposerState();
+    dispatchQueuedPrompt();
   }
 
   function closeConfigMenu(): void {
@@ -876,17 +1013,14 @@ export function createStructuredConnection(
       if (!commandMenu.contains(document.activeElement)) closeCommandMenu();
     }, 0);
   });
-  composerForm.addEventListener("submit", (e) => {
+  function dispatchPrompt(text: string, submittedAttachments: Attachment[] = []): void {
-    e.preventDefault();
-    const text = input.value;
-    if ((!text.trim() && attachments.length === 0) || input.disabled) return;
-    const submittedAttachments = attachments;
     uploading = submittedAttachments.length > 0;
     const generation = ++submissionGeneration;
     const submissionSocketGeneration = socketGeneration;
     awaitingBeginGeneration = generation;
     optimisticTurnStartedAt = Date.now();
     acceptedSubmission = null;
+    promptRequestPending = true;
     input.value = "";
     autoResize();
     clearError();
@@ -895,6 +1029,9 @@ export function createStructuredConnection(
       for (const attachment of submittedAttachments) {
         if (disposed) return;
         if (!attachment.path) attachment.path = (await uploadStructuredFile(sessionId, attachment.file)).path;
+        if (attachment.path && attachment.file.type.startsWith("image/")) {
+          imageObjectUrls.set(attachment.path, URL.createObjectURL(attachment.file));
+        }
       }
       if (disposed) return;
       const references = submittedAttachments.map(({ file, path }) =>
@@ -903,6 +1040,7 @@ export function createStructuredConnection(
     };
     void send().then(
       () => {
+        promptRequestPending = false;
         if (disposed || generation !== submissionGeneration) return;
         uploading = false;
         if (attachments === submittedAttachments) {
@@ -916,11 +1054,17 @@ export function createStructuredConnection(
         // A replacement socket may have captured idle before the POST claimed
         // the prompt. Reconnect again so its snapshot cannot predate the 204.
         if (acceptanceSocketGeneration > submissionSocketGeneration) reconnectForReconciliation();
+        renderComposerState();
+        dispatchQueuedPrompt();
       },
       (e: unknown) => {
+        promptRequestPending = false;
         uploading = false;
         if (disposed || generation !== submissionGeneration) return;
         if (awaitingBeginGeneration === generation) awaitingBeginGeneration = null;
+        if (attachments.length === 0 && submittedAttachments.length > 0) {
+          attachments = submittedAttachments;
+        }
         if (input.value === "") {
           input.value = text;
           autoResize();
@@ -929,6 +1073,32 @@ export function createStructuredConnection(
         renderComposerState();
       },
     );
+  }
+
+  function dispatchQueuedPrompt(): void {
+    const active = state.turn.responding || state.turn.thinking || awaitingBeginGeneration !== null;
+    if (disposed || active || promptRequestPending || promptQueue.length === 0) return;
+    const next = promptQueue.shift()!;
+    dispatchPrompt(next.text, next.attachments);
+  }
+
+  composerForm.addEventListener("submit", (e) => {
+    e.preventDefault();
+    const text = input.value;
+    if ((!text.trim() && attachments.length === 0) || uploading) return;
+    const submittedAttachments = attachments;
+    const active = state.turn.responding || state.turn.thinking || awaitingBeginGeneration !== null;
+    if (active || promptQueue.length > 0) {
+      promptQueue.push({ text, attachments: submittedAttachments });
+      attachments = [];
+      input.value = "";
+      autoResize();
+      clearError();
+      renderComposerState();
+      dispatchQueuedPrompt();
+      return;
+    }
+    dispatchPrompt(text, submittedAttachments);
   });
   cancelBtn.addEventListener("click", () => {
     clearError();
@@ -1101,6 +1271,8 @@ export function createStructuredConnection(
       closeCurrentSocket();
       expandedRowIds.clear();
       expandedGroupIds.clear();
+      for (const url of imageObjectUrls.values()) URL.revokeObjectURL(url);
+      imageObjectUrls.clear();
       scrollEl.removeEventListener("scroll", onTranscriptScroll);
       scrollEl.removeEventListener("click", onTranscriptClick, true);
       scrollEl.removeEventListener("wheel", stopSmoothFollow);

web/src/structuredRender.test.ts

@@ -368,13 +368,14 @@ describe("buildTranscriptRow: approval", () => {
     expect(el.querySelector(".st-approval-path")!.textContent).toBe("/etc/x");
   });
 
-  it("hides the buttons and shows an answered note once resolved", () => {
+  it("renders a compact one-liner once resolved", () => {
     const el = buildTranscriptRow(approvalRow(allThreeOptions), {
       pending: false,
       onDecide: () => Promise.resolve(),
     });
     expect(el.querySelector(".st-approval-acts")).toBeNull();
-    expect(el.querySelector(".st-approval-resolved")!.textContent).toBe("answered");
+    expect(el.classList.contains("st-approval-compact")).toBe(true);
+    expect(el.textContent).toContain("approved");
   });
 
   it("invokes onDecide with the clicked decision and disables the buttons", () => {

web/src/structuredRender.ts

@@ -581,7 +581,9 @@ export function buildToolGroup(
   children: HTMLElement[],
   expanded: boolean,
   onExpandedChange?: (expanded: boolean) => void,
+  toolCount?: number,
 ): HTMLElement {
+  const count = toolCount ?? rows.length;
   const wrap = el("div", "st-tool-group");
   wrap.dataset.toolGroupId = id;
   const head = document.createElement("button");
@@ -593,7 +595,7 @@ export function buildToolGroup(
   glyph.textContent = "›";
   glyph.setAttribute("aria-hidden", "true");
   const title = el("span", "st-tool-group-title");
-  title.textContent = `${rows.length} tool calls`;
+  title.textContent = `${count} tool calls`;
   head.append(glyph, title);
 
   const body = el("div", "st-tool-group-body st-disclosure");
@@ -702,6 +704,16 @@ function offeredDecisions(options: AcpPermissionOption[]): StructuredApprovalDec
 function buildApprovalRow(row: TranscriptRow, approval: ApprovalRowState): HTMLElement {
   const request = (row.data ?? {}) as { toolCall?: AcpToolCallLike; options?: AcpPermissionOption[] };
   const toolCall = request.toolCall ?? {};
+
+  // Resolved approvals render as a compact one-liner inside a tool group
+  // (or are hidden entirely when standalone — see rebuildTranscript).
+  if (!approval.pending) {
+    const wrap = el("div", "st-row st-row-approval st-approval-compact");
+    const label = toolCall.title ?? toolKindLabel(toolCall.kind);
+    wrap.textContent = `${label} — approved`;
+    return wrap;
+  }
+
   const wrap = el("div", "st-row st-row-approval");
   const card = el("div", "st-approval");
   wrap.appendChild(card);
@@ -721,45 +733,39 @@ function buildApprovalRow(row: TranscriptRow, approval: ApprovalRowState): HTMLE
     card.appendChild(pathEl);
   }
 
-  if (approval.pending) {
+  const acts = el("div", "st-approval-acts");
-    const acts = el("div", "st-approval-acts");
+  const mk = (label: string, decision: StructuredApprovalDecision, cls: string) => {
-    const mk = (label: string, decision: StructuredApprovalDecision, cls: string) => {
+    const btn = document.createElement("button");
-      const btn = document.createElement("button");
+    btn.type = "button";
-      btn.type = "button";
+    btn.className = cls ? `act ${cls}` : "act";
-      btn.className = cls ? `act ${cls}` : "act";
+    btn.textContent = label;
-      btn.textContent = label;
+    btn.addEventListener("click", () => {
-      btn.addEventListener("click", () => {
+      const buttons = [...acts.querySelectorAll<HTMLButtonElement>("button")];
-        const buttons = [...acts.querySelectorAll<HTMLButtonElement>("button")];
+      buttons.forEach((b) => (b.disabled = true));
-        buttons.forEach((b) => (b.disabled = true));
+      approval.onDecide(decision).catch(() => {
-        approval.onDecide(decision).catch(() => {
+        // Rejects only when this approval is still pending (see
-          // Rejects only when this approval is still pending (see
+        // ApprovalRowState) — restore the controls so the operator can
-          // ApprovalRowState) — restore the controls so the operator can
+        // retry; the error itself is surfaced by the connection.
-          // retry; the error itself is surfaced by the connection.
+        buttons.forEach((b) => (b.disabled = false));
-          buttons.forEach((b) => (b.disabled = false));
-        });
       });
-      return btn;
+    });
-    };
+    return btn;
-    const offered = offeredDecisions(request.options ?? []);
+  };
-    const specs: [StructuredApprovalDecision, string, string][] = [
+  const offered = offeredDecisions(request.options ?? []);
-      ["allow_once", "Allow once", "primary"],
+  const specs: [StructuredApprovalDecision, string, string][] = [
-      ["allow_for_session", "Allow for session", ""],
+    ["allow_once", "Allow once", "primary"],
-      ["deny", "Deny", "deny"],
+    ["allow_for_session", "Allow for session", ""],
-    ];
+    ["deny", "Deny", "deny"],
-    for (const [decision, label, cls] of specs) {
+  ];
-      if (offered.includes(decision)) acts.appendChild(mk(label, decision, cls));
+  for (const [decision, label, cls] of specs) {
-    }
+    if (offered.includes(decision)) acts.appendChild(mk(label, decision, cls));
-    if (acts.children.length > 0) {
+  }
-      card.appendChild(acts);
+  if (acts.children.length > 0) {
-    } else {
+    card.appendChild(acts);
-      const none = el("div", "st-approval-resolved");
-      none.textContent = "no decision offered";
-      card.appendChild(none);
-    }
   } else {
-    const resolved = el("div", "st-approval-resolved");
+    const none = el("div", "st-approval-resolved");
-    resolved.textContent = "answered";
+    none.textContent = "no decision offered";
-    card.appendChild(resolved);
+    card.appendChild(none);
   }
 
   return wrap;

web/src/styles.css

@@ -2290,6 +2290,9 @@ input.leaf-rename:focus {
 .structured-main {
   min-width: 0;
   min-height: 0;
+  max-width: 820px;
+  margin-inline: auto;
+  width: 100%;
   display: flex;
   flex-direction: column;
   flex: 1 1 auto;
@@ -2306,9 +2309,6 @@ input.leaf-rename:focus {
   display: flex;
   flex-direction: column;
   min-width: 0;
-  max-width: 820px;
-  margin-inline: auto;
-  width: 100%;
 }
 
 .structured-activity {
@@ -2318,9 +2318,7 @@ input.leaf-rename:focus {
   gap: var(--sp-2);
   min-height: 30px;
   padding: var(--sp-1) var(--sp-3);
-  border-top: 1px solid var(--border);
   color: var(--muted);
-  background: var(--surface-2);
   font-size: var(--fs-11);
   font-variant-numeric: tabular-nums;
 }
@@ -2382,6 +2380,15 @@ input.leaf-rename:focus {
   overflow-wrap: anywhere;
 }
 
+.st-user-image {
+  display: block;
+  max-width: min(100%, 480px);
+  max-height: 360px;
+  margin-top: var(--sp-2);
+  border-radius: var(--r-1);
+  object-fit: contain;
+}
+
 /* agent prose: no card, no background — plain text is the point */
 .st-row-agent .st-body p {
   margin: 0 0 var(--sp-2);
@@ -2898,6 +2905,26 @@ input.leaf-rename:focus {
   border-radius: var(--r-1);
 }
 
+/* intermediate agent text inside a tool group — subdued so the final
+   answer outside the group stays the prominent one. */
+.st-tool-group-body .st-row-agent {
+  color: var(--muted);
+  font-size: var(--fs-12);
+  padding: var(--sp-1) var(--sp-2);
+}
+
+.st-tool-group-body .st-row-agent .st-body > :first-child {
+  margin-top: 0;
+}
+
+.st-tool-group-body .st-row-agent .st-body > :last-child {
+  margin-bottom: 0;
+}
+
+.st-tool-group-body .st-row-thought {
+  padding: var(--sp-1) var(--sp-2);
+}
+
 .st-tool-group-body[hidden] {
   display: none;
 }
@@ -3020,6 +3047,16 @@ input.leaf-rename:focus {
   color: var(--faint);
 }
 
+/* compact resolved approval inside a tool group — same muted treatment
+   as intermediate agent text so the audit trail is preserved without
+   drawing attention to itself. */
+.st-approval-compact {
+  color: var(--muted);
+  font-size: var(--fs-12);
+  padding: var(--sp-1) var(--sp-2);
+  font-style: italic;
+}
+
 .act {
   appearance: none;
   font: inherit;
@@ -3073,6 +3110,7 @@ input.leaf-rename:focus {
    hairline that doubles as the focus indicator. Inner metrics line the draft
    up with the transcript's own 12px gutter. */
 .structured-composer {
+  position: relative;
   flex: 0 0 auto;
   padding: var(--sp-1) var(--sp-1) max(var(--sp-1), env(safe-area-inset-bottom));
   border-top: 1px solid var(--border);
@@ -3083,8 +3121,21 @@ input.leaf-rename:focus {
   transition: border-color var(--dur-fast) var(--ease-out);
 }
 
+.structured-queue {
+  position: absolute;
+  right: var(--sp-2);
+  bottom: calc(100% + var(--sp-1));
+  padding: 3px var(--sp-2);
+  border: 1px solid var(--border);
+  border-radius: var(--r-pill);
+  background: var(--surface);
+  color: var(--muted);
+  font-size: var(--fs-11);
+  box-shadow: var(--shadow-1);
+}
+
 .structured-composer:focus-within {
-  border-top-color: var(--accent);
+  border-top-color: var(--border);
 }
 
 .structured-input-wrap {
@@ -3200,7 +3251,9 @@ input.leaf-rename:focus {
 }
 
 .structured-composer .structured-cancel {
-  padding: 0 var(--sp-3);
+  position: relative;
+  width: 40px;
+  padding: 0;
   border-color: color-mix(in oklab, var(--danger) 35%, var(--border));
   color: var(--danger);
 }
@@ -3209,6 +3262,23 @@ input.leaf-rename:focus {
   background: var(--danger-tint);
 }
 
+.structured-cancel-stop {
+  width: 16px;
+  height: 16px;
+}
+
+.structured-cancel-spinner {
+  position: absolute;
+  inset: 4px;
+  width: auto;
+  height: auto;
+  animation: cancel-spin 0.8s linear infinite;
+}
+
+@keyframes cancel-spin {
+  to { transform: rotate(360deg); }
+}
+
 @media (max-width: 520px) {
   /* One row cannot hold a draft plus three controls at phone width — the
      draft gets a line of its own and the controls drop below it. */
@@ -3598,61 +3668,78 @@ input.leaf-rename:focus {
   color: var(--ink);
 }
 
-/* One-click tiles: host row + command row. */
+/* Harness cards: the first decision in the spawn form — which tool runs. */
-.tile-row {
+.harness-grid {
-  display: flex;
+  display: grid;
-  flex-wrap: wrap;
+  grid-template-columns: repeat(auto-fill, minmax(120px, 1fr));
   gap: var(--sp-2);
 }
 
-.tile {
+.harness-card {
-  flex: 1 1 auto;
-  min-width: 96px;
   display: flex;
   flex-direction: column;
-  gap: 2px;
+  align-items: center;
-  align-items: flex-start;
+  gap: var(--sp-2);
-  padding: var(--sp-2) var(--sp-3);
+  padding: var(--sp-3) var(--sp-2);
   background: var(--surface-2);
   border: 1px solid var(--border);
   border-radius: var(--r-2);
   color: var(--ink);
   font-family: inherit;
   cursor: pointer;
-  text-align: left;
+  text-align: center;
   transition:
     border-color var(--dur-fast) var(--ease-out),
     background var(--dur-fast) var(--ease-out);
 }
 
-.tile:hover {
+.harness-card:hover {
   border-color: var(--border-strong);
+  background: var(--surface-3);
 }
 
-.tile.is-active {
+.harness-card.is-active {
   border-color: var(--accent);
   background: var(--accent-tint);
 }
 
-.tile-label {
+.harness-icon {
-  font-size: var(--fs-14);
+  display: flex;
-  font-weight: 600;
-}
-
-.tile-sub {
-  font-size: var(--fs-12);
-  color: var(--muted);
-  font-family: var(--font-mono);
-}
-
-.tile-more {
-  flex: 0 0 auto;
-  min-width: 0;
-  justify-content: center;
   align-items: center;
+  justify-content: center;
+  width: 32px;
+  height: 32px;
   color: var(--muted);
 }
 
+.harness-card.is-active .harness-icon {
+  color: var(--ink);
+}
+
+.harness-icon .tool-icon {
+  display: block;
+}
+
+.harness-label {
+  font-size: var(--fs-13);
+  font-weight: 600;
+  white-space: nowrap;
+  overflow: hidden;
+  text-overflow: ellipsis;
+  max-width: 100%;
+}
+
+/* The "Custom…" card is an escape hatch, not a peer tool — dashed border
+   and subdued color separate it from the named harnesses. */
+.harness-custom {
+  border-style: dashed;
+  color: var(--muted);
+}
+
+.harness-custom .harness-label {
+  font-weight: 500;
+}
+
 /* Working-directory picker (#95). Two steps: a grid of project boxes, then the
    picked project's worktree choices. Stale beyond 7 days dims but stays
    selectable. */
@@ -3679,7 +3766,7 @@ input.leaf-rename:focus {
 
 .picker.projects {
   display: grid;
-  grid-template-columns: repeat(auto-fill, minmax(190px, 1fr));
+  grid-template-columns: repeat(2, 1fr);
   align-content: start;
   gap: var(--sp-2);
   max-height: 300px;
@@ -3735,19 +3822,6 @@ input.leaf-rename:focus {
   overflow-wrap: anywhere;
 }
 
-.project-meta {
-  font-family: var(--font-mono);
-  font-size: var(--fs-12);
-  color: var(--faint);
-  overflow: hidden;
-  text-overflow: ellipsis;
-  white-space: nowrap;
-}
-
-.project-meta:empty {
-  display: none;
-}
-
 .project-other {
   align-self: flex-start;
   padding: 4px 0;

web/src/types.ts

@@ -11,7 +11,7 @@ export type SessionStatus = "Running" | "Dead";
 /** Daemon-inferred activity dimension, orthogonal to `SessionStatus` (NAP-340).
  * Absent on payloads from daemons that predate the field. `Error` is only set
  * when an agent reports failure (#105); the daemon never infers it. */
-export type ActivityState = "Active" | "Idle" | "AwaitingInput" | "Error";
+export type ActivityState = "Active" | "Idle" | "AwaitingInput" | "Error" | "Starting";
 
 export interface Session {
   id: Uuid;