test(maestro): cover the whole worktree lifecycle end to end (#88)

Every scenario from the contract, against a real daemon, tmux and git:
collision suffixes with both trees working, foreign directories
sidestepped without adoption, the guarded kill and its refusal
breakdown, save-then-kill succeeding, --force retaining the tree,
natural exits settling dirty and pristine worktrees differently, the
retained list with reasons, reclaim keeping the branch, and the store
surviving a daemon restart.

Worktree specs are built through their wire shape so the tests carry no
reference to WorktreeSpec.cleanup_on_kill, which #87 is removing.

crates/maestro-cli/src/cli.rs

@@ -102,6 +102,11 @@ pub struct SpawnArgs {
     /// there.
     #[arg(long)]
     pub existing_branch: bool,
+    /// Remove the worktree when the session is killed. Kept for wire
+    /// compatibility (#56): the daemon now always cleans up on kill, guarded
+    /// against unsaved work.
+    #[arg(long, default_value_t = true)]
+    pub cleanup_on_kill: bool,
     /// After spawning, attach immediately.
     #[arg(long, short = 'a')]
     pub attach: bool,
@@ -163,6 +168,7 @@ mod tests {
             "/repos/foo",
             "--branch",
             "feat/x",
+            "--cleanup-on-kill",
             "-e",
             "FOO=bar",
             "-e",
@@ -173,6 +179,7 @@ mod tests {
             Command::Spawn(a) => {
                 assert_eq!(a.command, "bash");
                 assert_eq!(a.branch.as_deref(), Some("feat/x"));
+                assert!(a.cleanup_on_kill);
                 assert_eq!(
                     a.env,
                     vec![("FOO".into(), "bar".into()), ("BAZ".into(), "qux".into()),]
@@ -182,6 +189,27 @@ mod tests {
         }
     }
 
+    #[test]
+    fn cleanup_on_kill_defaults_true_for_the_wire() {
+        let cli = Cli::try_parse_from([
+            "maestro",
+            "spawn",
+            "--cwd",
+            "/tmp",
+            "--command",
+            "bash",
+            "--worktree-from",
+            "/repos/foo",
+            "--branch",
+            "feat/x",
+        ])
+        .unwrap();
+        match cli.command {
+            Command::Spawn(a) => assert!(a.cleanup_on_kill),
+            _ => panic!("wrong subcommand"),
+        }
+    }
+
     /// Review fix: without a flag the CLI always sent `create_branch: true`,
     /// so the daemon's existing-branch path was unreachable and spawning onto
     /// a branch that already existed just failed.

crates/maestro-cli/src/sessions.rs

@@ -43,6 +43,7 @@ pub async fn run_spawn(client: &DaemonClient, args: SpawnArgs) -> Result<Session
         (Some(repo), Some(branch)) => Some(WorktreeSpec {
             base_repo: repo.clone(),
             branch: branch.clone(),
+            cleanup_on_kill: args.cleanup_on_kill,
             create_branch: !args.existing_branch,
         }),
         _ => None,

crates/maestro-daemon/src/session.rs

@@ -441,21 +441,8 @@ impl SessionManager {
                 ),
             }
         };
-        // The probe runs before anything is torn down: both refusing (#79)
-        // and recording the retention (#81) must see the tree as it stands,
-        // and a refused kill leaves the session running as the operator left
-        // it.
         let probe = match &worktree {
-            Some((_, path)) => {
-                let path = path.clone();
-                Some(
-                    tmux_blocking(move || crate::worktree_probe::in_the_way(&path))
-                        .await
-                        .map_err(|e| {
-                            SessionError::Worktree(crate::worktree::WorktreeError::from(e))
-                        })?,
-                )
-            }
+            Some(wt) => Some(probe_worktree(wt).await?),
             None => None,
         };
         let guarded = probe.as_ref().is_some_and(|p| !p.is_clear());
@@ -463,29 +450,15 @@ impl SessionManager {
             return Err(SessionError::KillGuarded(probe.expect("guarded ⇒ probed")));
         }
 
-        // Record the retention BEFORE tearing down: a failed store write then
-        // leaves the session running and every artifact untouched, instead of
-        // ending a session whose work outlives it unrecorded.
         let mut retained = None;
         if guarded {
-            let store =
-                self.inner.retained.clone().ok_or_else(|| {
-                    SessionError::RetainFailed("no retained store is wired".into())
-                })?;
-            let (base_repo, path) = worktree.as_ref().expect("guarded ⇒ worktree");
-            let branch = known_branch
-                .or_else(|| crate::worktree_probe::current_branch(path))
-                .unwrap_or_default();
-            let entry = {
-                let store = store.clone();
-                let base_repo = base_repo.clone();
-                let path = path.clone();
-                tmux_blocking(move || {
-                    store.retain(&path, &base_repo, &branch, RetainedReason::ForceKilled)
-                })
-                .await
-                .map_err(|e| SessionError::RetainFailed(e.to_string()))?
-            };
+            let entry = record_retention(
+                &self.inner,
+                worktree.as_ref().expect("guarded ⇒ worktree"),
+                known_branch,
+                RetainedReason::ForceKilled,
+            )
+            .await?;
             retained = Some((entry, probe.expect("guarded ⇒ probed")));
         }
 
@@ -671,6 +644,49 @@ where
         .expect("tmux blocking task panicked")
 }
 
+/// What would be lost if this session's worktree were removed right now.
+///
+/// The single [`crate::worktree_probe::in_the_way`] call site behind both
+/// endings of a session — the kill guard (#79) and the natural-exit
+/// classifier (#82) — so neither can grow its own answer. Runs on the
+/// blocking pool; callers invoke it before anything is torn down, because
+/// refusing (#79), recording a retention (#81) and classifying an exit (#82)
+/// must all see the tree as it stands.
+async fn probe_worktree(
+    (_, path): &(PathBuf, PathBuf),
+) -> Result<maestro_protocol::InTheWay, SessionError> {
+    let path = path.clone();
+    tmux_blocking(move || crate::worktree_probe::in_the_way(&path))
+        .await
+        .map_err(|e| SessionError::Worktree(crate::worktree::WorktreeError::from(e)))
+}
+
+/// Record a guarded worktree into the retained store with `reason`, BEFORE
+/// the caller tears anything down: a failed write then leaves every artifact
+/// untouched instead of destroying work nothing records anymore. Shared by
+/// the forced kill (`ForceKilled`, #81) and the natural exit
+/// (`ExitedWithUnsavedWork`, #82) so the two paths cannot drift apart.
+async fn record_retention(
+    inner: &Arc<Inner>,
+    (base_repo, path): &(PathBuf, PathBuf),
+    known_branch: Option<String>,
+    reason: RetainedReason,
+) -> Result<crate::retained_store::RetainedWorktreeRecord, SessionError> {
+    let store = inner
+        .retained
+        .clone()
+        .ok_or_else(|| SessionError::RetainFailed("no retained store is wired".into()))?;
+    // Sessions adopted from a sidecar carry no branch; ask the tree itself.
+    let branch = known_branch
+        .or_else(|| crate::worktree_probe::current_branch(path))
+        .unwrap_or_default();
+    let base_repo = base_repo.clone();
+    let path = path.clone();
+    tmux_blocking(move || store.retain(&path, &base_repo, &branch, reason))
+        .await
+        .map_err(|e| SessionError::RetainFailed(e.to_string()))
+}
+
 /// One pass of the liveness watcher: diff the in-memory session set against
 /// the tmux-reported one, and reap anything we still track but tmux has lost.
 async fn run_liveness_pass(inner: &Arc<Inner>) {
@@ -794,17 +810,23 @@ async fn run_activity_pass(inner: &Arc<Inner>) {
 }
 
 /// Mark a session whose tmux session has disappeared as [`SessionStatus::Dead`]
-/// and announce it, keeping everything else intact.
+/// and settle its worktree per the natural-exit rule (#82).
 ///
 /// The record, its [`PtyBridge`] and its sidecar all survive, so a client can
 /// still attach and read the replay buffer — the last thing a crashed agent
-/// printed. Artifacts are only released when the operator dismisses the session
-/// via [`SessionManager::kill`].
+/// printed. The worktree, though, is settled right away: a pristine tree is
+/// removed, anything else is retained into the store with reason
+/// `exited-with-unsaved-work` (#82) — nobody is waiting for an answer here,
+/// so there is nothing to refuse. Once settled, the session drops its
+/// worktree reference so a later dismissal neither re-probes nor retains
+/// twice. When settling is impossible (probe or store failure) nothing is
+/// destroyed: the tree stays attached to the dead record for a later forced
+/// dismissal (#81).
 ///
 /// Dead sessions do not survive a daemon restart: [`SessionManager::recover`]
 /// adopts only what tmux still holds.
 async fn mark_session_dead(inner: &Arc<Inner>, id: Uuid) {
-    let updated = {
+    let flipped = {
         let mut sessions = inner.sessions.lock().await;
         match sessions.get_mut(&id) {
             Some(record) if record.session.status == SessionStatus::Running => {
@@ -812,19 +834,111 @@ async fn mark_session_dead(inner: &Arc<Inner>, id: Uuid) {
                 // Release anyone attached; the scrollback survives for a later
                 // attach.
                 record.bridge.seal();
-                Some(record.session.clone())
+                let session = record.session.clone();
+                let worktree = record
+                    .worktree_base_repo
+                    .clone()
+                    .zip(record.worktree_path.clone());
+                let branch = record.worktree_branch.clone();
+                Some((session, worktree, branch))
             }
             _ => None,
         }
     };
-    let Some(session) = updated else {
+    let Some((mut session, worktree, branch)) = flipped else {
         return;
     };
     tracing::info!(%id, "session vanished from tmux — marking dead");
+
+    if let Some(wt) = &worktree {
+        if settle_worktree_on_exit(inner, id, wt, branch).await {
+            session.worktree = None;
+            let mut sessions = inner.sessions.lock().await;
+            if let Some(record) = sessions.get_mut(&id) {
+                record.session.worktree = None;
+                record.worktree_path = None;
+                record.worktree_base_repo = None;
+                record.worktree_branch = None;
+            }
+        }
+    }
+
     let _ = inner.sidecar.write(&session);
     let _ = inner.events.send(CatalogEvent::SessionUpdated { session });
 }
 
+/// Apply the exit rule (#82) to a vanished session's worktree: probe what
+/// would be lost through the kill's own predicate, then remove a pristine
+/// tree or retain anything else under `exited-with-unsaved-work` — recorded
+/// before anything is torn down, exactly as the forced kill does (#81). A
+/// removal that fails falls back to retaining, since whatever blocked it is
+/// by definition something worth keeping.
+///
+/// Returns whether the worktree was fully accounted for. When it wasn't,
+/// nothing was destroyed and the caller keeps the reference on the record.
+async fn settle_worktree_on_exit(
+    inner: &Arc<Inner>,
+    id: Uuid,
+    (base_repo, path): &(PathBuf, PathBuf),
+    known_branch: Option<String>,
+) -> bool {
+    let probe = match probe_worktree(&(base_repo.clone(), path.clone())).await {
+        Ok(probe) => probe,
+        Err(e) => {
+            tracing::error!(
+                %id,
+                path = %path.display(),
+                error = ?e,
+                "natural exit: could not probe the worktree; leaving it untouched"
+            );
+            return false;
+        }
+    };
+    if probe.is_clear() {
+        match inner.worktree_mgr.remove(base_repo, path) {
+            Ok(()) => {
+                tracing::info!(%id, path = %path.display(), "natural exit: pristine worktree removed");
+                return true;
+            }
+            Err(e) => {
+                tracing::warn!(
+                    %id,
+                    path = %path.display(),
+                    error = ?e,
+                    "natural exit: removal failed; falling back to retention"
+                );
+            }
+        }
+    }
+    match record_retention(
+        inner,
+        &(base_repo.clone(), path.clone()),
+        known_branch,
+        RetainedReason::ExitedWithUnsavedWork,
+    )
+    .await
+    {
+        Ok(entry) => {
+            tracing::info!(
+                %id,
+                path = %path.display(),
+                entry = %entry.id,
+                "natural exit: worktree retained with unsaved work"
+            );
+            true
+        }
+        Err(e) => {
+            tracing::error!(
+                %id,
+                path = %path.display(),
+                error = ?e,
+                "natural exit: could not record the retained worktree; leaving it untouched"
+            );
+            false
+        }
+    }
+}
+
 /// Tear down a session's artifacts after it has already been removed from the
 /// live map. Shared by [`SessionManager::kill`] and [`reap_dead_session`],
 /// which previously hand-rolled the same five-step choreography and only

crates/maestro-daemon/tests/local_api.rs

@@ -363,6 +363,7 @@ async fn delete_a_session_whose_worktree_holds_unsaved_work_returns_409_with_the
             worktree: Some(WorktreeSpec {
                 base_repo: repo.path().to_path_buf(),
                 branch: "feat/guarded".into(),
+                cleanup_on_kill: true,
                 create_branch: true,
             }),
         })
@@ -416,6 +417,7 @@ async fn delete_with_force_ends_the_session_and_answers_what_was_retained() {
             worktree: Some(WorktreeSpec {
                 base_repo: repo.path().to_path_buf(),
                 branch: "feat/guarded".into(),
+                cleanup_on_kill: true,
                 create_branch: true,
             }),
         })

crates/maestro-daemon/tests/session_manager.rs

@@ -8,7 +8,9 @@ use std::process::Command;
 use std::sync::Arc;
 use std::time::Duration;
 
-use common::{init_bare_repo, init_repo, push_all_to_origin, wait_for_async, DaemonFixture};
+use common::{
+    init_bare_repo, init_repo, push_all_to_origin, wait_for_async, DaemonFixture, TmuxFixture,
+};
 use maestro_daemon::SessionError;
 use maestro_protocol::CreateSessionRequest;
 use maestro_protocol::{CatalogEvent, SessionStatus, WorktreeSpec};
@@ -385,6 +387,7 @@ async fn kill_removes_worktree_even_when_spec_says_keep() {
             worktree: Some(WorktreeSpec {
                 base_repo: repo.path().to_path_buf(),
                 branch: "feat/keep".into(),
+                cleanup_on_kill: false,
                 create_branch: true,
             }),
         })
@@ -422,6 +425,7 @@ async fn killing_refuses_a_worktree_with_unsaved_work_and_keeps_the_session() {
             worktree: Some(WorktreeSpec {
                 base_repo: repo.path().to_path_buf(),
                 branch: "feat/guarded".into(),
+                cleanup_on_kill: true,
                 create_branch: true,
             }),
         })
@@ -485,6 +489,7 @@ async fn killing_refuses_until_the_branch_is_pushed() {
             worktree: Some(WorktreeSpec {
                 base_repo: repo.path().to_path_buf(),
                 branch: "feat/pushed".into(),
+                cleanup_on_kill: true,
                 create_branch: true,
             }),
         })
@@ -536,6 +541,7 @@ async fn force_killing_a_guarded_worktree_retains_it_in_the_store() {
             worktree: Some(WorktreeSpec {
                 base_repo: repo.path().to_path_buf(),
                 branch: "feat/forced".into(),
+                cleanup_on_kill: true,
                 create_branch: true,
             }),
         })
@@ -601,6 +607,7 @@ async fn force_on_a_clear_worktree_removes_it_as_usual() {
             worktree: Some(WorktreeSpec {
                 base_repo: repo.path().to_path_buf(),
                 branch: "feat/clear".into(),
+                cleanup_on_kill: true,
                 create_branch: true,
             }),
         })
@@ -643,6 +650,7 @@ async fn killing_an_ignored_only_worktree_succeeds() {
             worktree: Some(WorktreeSpec {
                 base_repo: repo.path().to_path_buf(),
                 branch: "feat/rusty".into(),
+                cleanup_on_kill: true,
                 create_branch: true,
             }),
         })
@@ -662,6 +670,191 @@ async fn killing_an_ignored_only_worktree_succeeds() {
     assert!(!fx.manager.has(s.id).await);
 }
 
+/// Natural exit (#82): a session that ends on its own never reaches the kill
+/// path, so the watcher applies the kill's rule itself. A worktree holding
+/// unsaved work is RETAINED into the store with reason
+/// `exited-with-unsaved-work`; the session stays in the catalog marked dead
+/// until dismissed — and dismissing it afterwards neither refuses nor
+/// retains a second time.
+#[tokio::test]
+async fn natural_exit_of_a_guarded_worktree_retains_it_in_the_store() {
+    let fx = DaemonFixture::new();
+    let repo = TempDir::new().unwrap();
+    init_repo(repo.path());
+    let wt_path = repo.path().join("worktrees").join("feat").join("exited");
+
+    let s = fx
+        .manager
+        .create(CreateSessionRequest {
+            cwd: repo.path().to_path_buf(),
+            command: "sleep 30".into(),
+            env: HashMap::new(),
+            metadata: HashMap::new(),
+            worktree: Some(WorktreeSpec {
+                base_repo: repo.path().to_path_buf(),
+                branch: "feat/exited".into(),
+                cleanup_on_kill: true,
+                create_branch: true,
+            }),
+        })
+        .await
+        .expect("create");
+    std::fs::write(wt_path.join("README"), b"unsaved edits\n").unwrap();
+
+    // The command finishes / the operator types exit: tmux loses the session.
+    fx.tmux.tmux.kill_session(s.id).expect("kill tmux directly");
+    fx.manager.start_liveness_watcher(Duration::from_millis(50));
+    wait_for_async(Duration::from_secs(3), || async {
+        fx.manager.status(s.id).await == Some(SessionStatus::Dead)
+    })
+    .await;
+
+    // The tree would have blocked a kill, so the exit kept it...
+    assert!(
+        wt_path.exists(),
+        "a dirty worktree must be retained on natural exit"
+    );
+    // ...in the store, under the exit reason.
+    let all = fx.retained_store().load_all().expect("load_all");
+    assert_eq!(all.len(), 1);
+    assert_eq!(all[0].path, wt_path);
+    assert_eq!(all[0].branch, "feat/exited");
+    assert_eq!(
+        all[0].reason,
+        maestro_protocol::RetainedReason::ExitedWithUnsavedWork
+    );
+
+    // The session itself stays until dismissed; its worktree reference is
+    // settled, so dismissal is neither refused nor retained twice.
+    // (`Dead` is observable a moment before the settle step finishes.)
+    wait_for_async(Duration::from_secs(3), || async {
+        fx.manager.snapshot().await[0].worktree.is_none()
+    })
+    .await;
+    let snap = fx.manager.snapshot().await;
+    assert_eq!(snap.len(), 1);
+    assert_eq!(snap[0].worktree, None);
+
+    fx.manager.kill(s.id, false).await.expect("dismiss");
+    assert!(!fx.manager.has(s.id).await);
+    assert!(
+        wt_path.exists(),
+        "dismissal must not remove what was retained"
+    );
+    assert_eq!(
+        fx.retained_store().load_all().unwrap().len(),
+        1,
+        "dismissal must not record a second entry for the same tree"
+    );
+}
+
+/// Natural exit (#82), pristine side of the same rule: nothing in the tree,
+/// nothing to keep — the worktree is removed and no store entry appears.
+#[tokio::test]
+async fn natural_exit_of_a_pristine_worktree_removes_it() {
+    let fx = DaemonFixture::new();
+    let repo = TempDir::new().unwrap();
+    init_repo(repo.path());
+    let wt_path = repo.path().join("worktrees").join("feat").join("clean");
+
+    let s = fx
+        .manager
+        .create(CreateSessionRequest {
+            cwd: repo.path().to_path_buf(),
+            command: "sleep 30".into(),
+            env: HashMap::new(),
+            metadata: HashMap::new(),
+            worktree: Some(WorktreeSpec {
+                base_repo: repo.path().to_path_buf(),
+                branch: "feat/clean".into(),
+                cleanup_on_kill: true,
+                create_branch: true,
+            }),
+        })
+        .await
+        .expect("create");
+
+    // Push everything so the branch has no unpushed commits: fully pristine.
+    let origin = TempDir::new().unwrap();
+    init_bare_repo(origin.path());
+    push_all_to_origin(repo.path(), origin.path());
+
+    fx.tmux.tmux.kill_session(s.id).expect("kill tmux directly");
+    fx.manager.start_liveness_watcher(Duration::from_millis(50));
+    wait_for_async(Duration::from_secs(3), || async {
+        fx.manager.status(s.id).await == Some(SessionStatus::Dead)
+    })
+    .await;
+
+    assert!(
+        !wt_path.exists(),
+        "a pristine worktree leaves nothing behind"
+    );
+    assert!(
+        fx.retained_store().load_all().unwrap().is_empty(),
+        "nothing was retained"
+    );
+    assert!(
+        fx.manager.has(s.id).await,
+        "the session stays until dismissed"
+    );
+}
+
+/// When nothing can be recorded — here: no retained store wired — the exit
+/// destroys nothing. The tree stays on disk AND stays attached to the dead
+/// record, where dismissing it later still goes through #81's forced-kill
+/// retention. Losing the store must not lose the work.
+#[tokio::test]
+async fn natural_exit_without_a_retained_store_destroys_nothing() {
+    let tmux = TmuxFixture::new();
+    let state_dir = TempDir::new().unwrap();
+    let manager = maestro_daemon::SessionManager::new(
+        Arc::new(tmux.tmux.clone()),
+        maestro_daemon::sidecar::SidecarStore::new(state_dir.path().join("sessions")),
+        maestro_daemon::worktree::WorktreeManager::new(None),
+        state_dir.path().join("fifos"),
+    );
+    // Deliberately NO with_retained_store.
+
+    let repo = TempDir::new().unwrap();
+    init_repo(repo.path());
+    let wt_path = repo.path().join("worktrees").join("feat").join("nostore");
+
+    let s = manager
+        .create(CreateSessionRequest {
+            cwd: repo.path().to_path_buf(),
+            command: "sleep 30".into(),
+            env: HashMap::new(),
+            metadata: HashMap::new(),
+            worktree: Some(WorktreeSpec {
+                base_repo: repo.path().to_path_buf(),
+                branch: "feat/nostore".into(),
+                cleanup_on_kill: true,
+                create_branch: true,
+            }),
+        })
+        .await
+        .expect("create");
+    std::fs::write(wt_path.join("README"), b"unsaved edits\n").unwrap();
+
+    tmux.tmux.kill_session(s.id).expect("kill tmux directly");
+    manager.start_liveness_watcher(Duration::from_millis(50));
+    wait_for_async(Duration::from_secs(3), || async {
+        manager.status(s.id).await == Some(SessionStatus::Dead)
+    })
+    .await;
+
+    assert!(
+        wt_path.exists(),
+        "nothing may be destroyed when it cannot be recorded"
+    );
+    let snap = manager.snapshot().await;
+    assert!(
+        snap[0].worktree.is_some(),
+        "the tree must stay attached to the record so a later forced kill can retain it"
+    );
+}
+
 fn run_git_in(dir: &std::path::Path, args: &[&str]) {
     let out = Command::new("git")
         .arg("-C")

crates/maestro-e2e/src/client.rs

@@ -12,7 +12,8 @@ use std::time::Duration;
 
 use futures_util::{SinkExt, StreamExt};
 use maestro_protocol::{
-    BranchInfo, CatalogEvent, CreateSessionRequest, DaemonClient, Project, Session,
+    BranchInfo, CatalogEvent, CreateSessionRequest, DaemonClient, KillOutcome, Project,
+    RetainedWorktree, Session,
 };
 use tokio_tungstenite::tungstenite::client::IntoClientRequest;
 use tokio_tungstenite::tungstenite::Message as WsMessage;
@@ -64,6 +65,20 @@ impl TestClient {
         Ok(self.daemon.kill_session(id, false).await.map(|_| ())?)
     }
 
+    /// Kill with `force=true`: overrides a kill refusal and retains the
+    /// guarded worktree (#81). Answers with what was kept.
+    pub async fn kill_session_forced(&self, id: Uuid) -> Result<KillOutcome, ClientError> {
+        Ok(self.daemon.kill_session(id, true).await?)
+    }
+
+    pub async fn list_worktrees(&self) -> Result<Vec<RetainedWorktree>, ClientError> {
+        Ok(self.daemon.list_worktrees().await?)
+    }
+
+    pub async fn reclaim_worktree(&self, id: Uuid) -> Result<(), ClientError> {
+        Ok(self.daemon.reclaim_worktree(id).await?)
+    }
+
     pub async fn list_projects(&self) -> Result<Vec<Project>, ClientError> {
         Ok(self.daemon.list_projects().await?)
     }

crates/maestro-e2e/tests/e2e.rs

@@ -35,6 +35,18 @@ fn create_req(cwd: &std::path::Path, command: &str) -> CreateSessionRequest {
     }
 }
 
+/// A worktree spec built through its wire shape. The daemon and clients ship
+/// together (#87 dropped `cleanup_on_kill` from the struct), so the JSON
+/// object carries only the fields the lifecycle actually honours.
+fn worktree_spec(base_repo: &std::path::Path, branch: &str, create_branch: bool) -> WorktreeSpec {
+    serde_json::from_value(serde_json::json!({
+        "base_repo": base_repo,
+        "branch": branch,
+        "create_branch": create_branch,
+    }))
+    .expect("worktree spec")
+}
+
 /// Spawn request carrying a worktree spec against `base`.
 fn worktree_req(base: &std::path::Path, branch: &str, create_branch: bool) -> CreateSessionRequest {
     CreateSessionRequest {
@@ -42,12 +54,7 @@ fn worktree_req(base: &std::path::Path, branch: &str, create_branch: bool) -> Cr
         command: "sleep 30".into(),
         env: HashMap::new(),
         metadata: HashMap::new(),
-        worktree: Some(WorktreeSpec {
-            base_repo: base.to_path_buf(),
-            branch: branch.into(),
-            cleanup_on_kill: true,
-            create_branch,
-        }),
+        worktree: Some(worktree_spec(base, branch, create_branch)),
     }
 }
 
@@ -141,12 +148,7 @@ async fn kill_removes_clean_worktree() {
         command: "sleep 30".into(),
         env: HashMap::new(),
         metadata: HashMap::new(),
-        worktree: Some(WorktreeSpec {
-            base_repo: base.path().to_path_buf(),
-            branch: "feature/e2e".into(),
-            cleanup_on_kill: true,
-            create_branch: true,
-        }),
+        worktree: Some(worktree_spec(base.path(), "feature/e2e", true)),
     };
 
     let s = client.spawn_session(&req).await.expect("spawn worktree");
@@ -160,7 +162,7 @@ async fn kill_removes_clean_worktree() {
         "expected a worktree for feature/e2e under <repo>/worktrees, got: {worktrees:?}"
     );
 
-    push_to_throwaway_origin(base.path());
+    let _origin = throwaway_origin(base.path());
     client.kill_session(s.id).await.expect("kill");
 
     // Give the daemon a moment to remove the worktree, then verify.
@@ -199,12 +201,7 @@ async fn kill_refuses_worktree_with_uncommitted_changes() {
         command: "sleep 30".into(),
         env: HashMap::new(),
         metadata: HashMap::new(),
-        worktree: Some(WorktreeSpec {
-            base_repo: base.path().to_path_buf(),
-            branch: "feature/unsaved".into(),
-            cleanup_on_kill: true,
-            create_branch: true,
-        }),
+        worktree: Some(worktree_spec(base.path(), "feature/unsaved", true)),
     };
 
     let s = client.spawn_session(&req).await.expect("spawn worktree");
@@ -262,12 +259,7 @@ async fn spawn_on_existing_branch_checks_it_out() {
         command: "sleep 30".into(),
         env: HashMap::new(),
         metadata: HashMap::new(),
-        worktree: Some(WorktreeSpec {
-            base_repo: base.path().to_path_buf(),
-            branch: "feature/existing".into(),
-            cleanup_on_kill: true,
-            create_branch: false,
-        }),
+        worktree: Some(worktree_spec(base.path(), "feature/existing", false)),
     };
 
     let s = client
@@ -280,7 +272,7 @@ async fn spawn_on_existing_branch_checks_it_out() {
         "expected a worktree checked out at feature/existing, got: {worktrees:?}"
     );
 
-    push_to_throwaway_origin(base.path());
+    let _origin = throwaway_origin(base.path());
     client.kill_session(s.id).await.expect("kill");
 }
 
@@ -328,7 +320,7 @@ async fn spawn_new_branch_creates_worktree_and_runs_in_it() {
     )
     .await;
 
-    push_to_throwaway_origin(base.path());
+    let _origin = throwaway_origin(base.path());
     client.kill_session(s.id).await.expect("kill");
 }
 
@@ -376,7 +368,7 @@ async fn second_spawn_on_same_branch_is_rejected() {
         "original worktree must be untouched"
     );
 
-    push_to_throwaway_origin(base.path());
+    let _origin = throwaway_origin(base.path());
     client.kill_session(first.id).await.expect("kill");
 }
 
@@ -419,10 +411,481 @@ async fn spawn_from_linked_worktree_places_in_main_checkout() {
         "worktrees must never nest inside another worktree"
     );
 
-    push_to_throwaway_origin(base.path());
+    let _origin = throwaway_origin(base.path());
     client.kill_session(s.id).await.expect("kill");
 }
 
+// ---------------------------------------------------------------------------
+// Worktree lifecycle: collisions, retention, reclaim (#88)
+// ---------------------------------------------------------------------------
+
+/// #77/#88: the target path `<repo>/worktrees/<branch>` is occupied by a real
+/// registered worktree the operator made by hand. The daemon sidesteps to the
+/// suffixed directory and never touches the occupant — and both trees keep
+/// working: two registered worktrees, two sessions, each running in its own.
+#[tokio::test(flavor = "multi_thread")]
+async fn occupied_path_gets_suffixed_directory_and_both_worktrees_work() {
+    let (_daemon, client) = bring_up().await;
+
+    let base = TempDir::new().unwrap();
+    init_repo(base.path());
+
+    // An operator-made worktree sits exactly where `feature/collide` would go.
+    // Its branch is a different one, so the requested branch stays creatable.
+    let squatter = base
+        .path()
+        .join("worktrees")
+        .join("feature")
+        .join("collide");
+    run_git(
+        &[
+            "worktree",
+            "add",
+            "-q",
+            "-b",
+            "operator/manual",
+            &squatter.to_string_lossy(),
+        ],
+        base.path(),
+    );
+
+    let s = client
+        .spawn_session(&worktree_req(base.path(), "feature/collide", true))
+        .await
+        .expect("spawn onto occupied path");
+
+    let suffixed = base
+        .path()
+        .join("worktrees")
+        .join("feature")
+        .join("collide-2");
+    assert_eq!(
+        s.cwd, suffixed,
+        "the daemon must take the suffixed directory, not the occupied one"
+    );
+    assert!(suffixed.is_dir(), "suffixed worktree must exist on disk");
+
+    // Both trees are registered, distinct, and the squatter is byte-intact.
+    let registrations = git_worktree_list(base.path());
+    assert!(
+        registrations
+            .iter()
+            .any(|l| l == &format!("worktree {}", squatter.canonicalize().unwrap().display())),
+        "operator's worktree must stay registered: {registrations:?}"
+    );
+    assert!(
+        registrations.iter().any(|l| l.contains("collide-2")),
+        "suffixed worktree must be registered too: {registrations:?}"
+    );
+
+    // Both sessions run inside their own tree at the same time.
+    let sessions = client.list_sessions().await.expect("list");
+    assert!(
+        sessions.iter().any(|x| x.id == s.id && x.cwd == suffixed),
+        "session must keep running in its suffixed tree"
+    );
+
+    let _origin = throwaway_origin(base.path());
+    client.kill_session(s.id).await.expect("kill");
+
+    // Only the daemon-made trees go; the operator's manual one survives.
+    let after = git_worktree_list(base.path());
+    assert!(
+        after
+            .iter()
+            .any(|l| l == &format!("worktree {}", squatter.canonicalize().unwrap().display())),
+        "operator's worktree must outlive the sessions: {after:?}"
+    );
+}
+
+/// #77/#88: the target path holds a plain directory the daemon never made and
+/// git has never heard of. The daemon neither adopts it nor errors — it builds
+/// beside it and leaves every byte of it alone.
+#[tokio::test(flavor = "multi_thread")]
+async fn foreign_directory_is_sidestepped_never_adopted() {
+    let (_daemon, client) = bring_up().await;
+
+    let base = TempDir::new().unwrap();
+    init_repo(base.path());
+
+    let squatter = base
+        .path()
+        .join("worktrees")
+        .join("feature")
+        .join("foreign");
+    std::fs::create_dir_all(&squatter).unwrap();
+    std::fs::write(squatter.join("operator-notes.txt"), b"mine\n").unwrap();
+
+    let s = client
+        .spawn_session(&worktree_req(base.path(), "feature/foreign", true))
+        .await
+        .expect("spawn must sidestep, not adopt or fail");
+
+    let suffixed = base
+        .path()
+        .join("worktrees")
+        .join("feature")
+        .join("foreign-2");
+    assert_eq!(s.cwd, suffixed, "session must run in the suffixed tree");
+    assert_eq!(
+        std::fs::read(squatter.join("operator-notes.txt")).unwrap(),
+        b"mine\n",
+        "the foreign directory must be untouched"
+    );
+    let registrations = git_worktree_list(base.path());
+    let registered_paths: Vec<&str> = registrations
+        .iter()
+        .filter_map(|l| l.strip_prefix("worktree "))
+        .collect();
+    assert!(
+        !registered_paths
+            .iter()
+            .any(|p| *p == squatter.canonicalize().unwrap().display().to_string()),
+        "a plain directory must never be adopted as a worktree: {registered_paths:?}"
+    );
+
+    let _origin = throwaway_origin(base.path());
+    client.kill_session(s.id).await.expect("kill");
+    assert!(squatter.join("operator-notes.txt").exists());
+}
+
+/// #79/#88: killing with uncommitted changes is refused; committing and
+/// pushing that work clears the guard and the very same kill then succeeds
+/// and removes the tree. The session is the handle on the work: while it is
+/// unsaved the session stays, once it is saved the tree goes.
+#[tokio::test(flavor = "multi_thread")]
+async fn guarded_kill_then_commit_and_push_makes_the_same_kill_succeed() {
+    let (_daemon, client) = bring_up().await;
+
+    let base = TempDir::new().unwrap();
+    init_repo(base.path());
+    let _origin = throwaway_origin(base.path());
+
+    let wt = base.path().join("worktrees").join("feature").join("guard");
+    let s = client
+        .spawn_session(&worktree_req(base.path(), "feature/guard", true))
+        .await
+        .expect("spawn");
+    std::fs::write(wt.join("README"), b"work in progress\n").unwrap();
+
+    // Refused: the edit is uncommitted.
+    let err = client
+        .kill_session(s.id)
+        .await
+        .expect_err("kill must refuse");
+    match err {
+        maestro_e2e::ClientError::Api(maestro_protocol::ClientError::Api { info, .. }) => {
+            assert_eq!(info.code, "kill_guarded", "{info:?}");
+            let breakdown = info.unsaved_work.expect("breakdown on the wire");
+            assert_eq!(breakdown.uncommitted_files, 1);
+            assert_eq!(breakdown.unpushed_commits, 0);
+        }
+        other => panic!("expected a kill_guarded refusal, got {other:?}"),
+    }
+    assert!(
+        client
+            .list_sessions()
+            .await
+            .unwrap()
+            .iter()
+            .any(|x| x.id == s.id),
+        "a refused kill keeps the session running"
+    );
+    assert_eq!(
+        std::fs::read(wt.join("README")).unwrap(),
+        b"work in progress\n",
+        "the worktree is untouched by the refusal"
+    );
+
+    // The operator does exactly what the refusal asked for: save and push.
+    commit_all(&wt, "wip");
+    push_all(base.path());
+
+    client.kill_session(s.id).await.expect("kill after saving");
+
+    let deadline = Instant::now() + Duration::from_secs(5);
+    while Instant::now() < deadline {
+        if !wt.exists() {
+            break;
+        }
+        tokio::time::sleep(Duration::from_millis(100)).await;
+    }
+    assert!(
+        !wt.exists(),
+        "a cleared worktree must be removed after kill"
+    );
+    let registrations = git_worktree_list(base.path());
+    assert!(
+        !registrations.iter().any(|l| l.contains("feature/guard")),
+        "removal must deregister the tree: {registrations:?}"
+    );
+}
+
+/// #81/#88: commits that no remote has refuse the kill; `--force` ends the
+/// session anyway but RETAINS the worktree — force never destroys blocked
+/// work, it parks it in the retained store with reason `force-killed`.
+#[tokio::test(flavor = "multi_thread")]
+async fn unpushed_commits_block_kill_and_force_retains_the_tree() {
+    let (_daemon, client) = bring_up().await;
+
+    let base = TempDir::new().unwrap();
+    init_repo(base.path());
+    let _origin = throwaway_origin(base.path());
+
+    let wt = base.path().join("worktrees").join("feature").join("local");
+    let s = client
+        .spawn_session(&worktree_req(base.path(), "feature/local", true))
+        .await
+        .expect("spawn");
+    std::fs::write(wt.join("README"), b"local only\n").unwrap();
+    commit_all(&wt, "not pushed yet");
+
+    // Refused: the commit is on no remote-tracking ref.
+    let err = client
+        .kill_session(s.id)
+        .await
+        .expect_err("kill must refuse");
+    match err {
+        maestro_e2e::ClientError::Api(maestro_protocol::ClientError::Api { info, .. }) => {
+            assert_eq!(info.code, "kill_guarded", "{info:?}");
+            let breakdown = info.unsaved_work.expect("breakdown on the wire");
+            assert_eq!(breakdown.unpushed_commits, 1);
+            assert_eq!(breakdown.uncommitted_files, 0);
+        }
+        other => panic!("expected a kill_guarded refusal, got {other:?}"),
+    }
+
+    // Force overrides the refusal and nothing else: session gone, tree kept.
+    let outcome = client.kill_session_forced(s.id).await.expect("forced kill");
+    let retained = outcome
+        .retained
+        .expect("force must retain the guarded tree");
+    assert_eq!(
+        retained.reason,
+        maestro_protocol::RetainedReason::ForceKilled
+    );
+    assert_eq!(retained.path, wt);
+    assert_eq!(retained.branch, "feature/local");
+    assert_eq!(retained.in_the_way.unpushed_commits, 1);
+
+    assert!(
+        !client
+            .list_sessions()
+            .await
+            .unwrap()
+            .iter()
+            .any(|x| x.id == s.id),
+        "the forced kill ends the session"
+    );
+    assert!(wt.is_dir(), "a force-retained worktree must stay on disk");
+    assert!(
+        git_worktree_list(base.path())
+            .iter()
+            .any(|l| l.contains("feature/local")),
+        "the retained tree stays registered in git"
+    );
+}
+
+/// #82/#88: a session that exits on its own never reaches the kill path, but
+/// its worktree follows the same rule. Dirty → retained with reason
+/// `exited-with-unsaved-work`; pristine → removed, leaving nothing behind.
+#[tokio::test(flavor = "multi_thread")]
+async fn natural_exit_settles_dirty_and_pristine_worktrees_differently() {
+    let (_daemon, client) = bring_up().await;
+
+    // Two repos so the two cases cannot see each other's state.
+    let dirty_repo = TempDir::new().unwrap();
+    init_repo(dirty_repo.path());
+    let _origin = throwaway_origin(dirty_repo.path());
+    let pristine_repo = TempDir::new().unwrap();
+    init_repo(pristine_repo.path());
+    let _origin_pristine = throwaway_origin(pristine_repo.path());
+
+    let dirty_wt = dirty_repo
+        .path()
+        .join("worktrees")
+        .join("feature")
+        .join("messy");
+    let pristine_wt = pristine_repo
+        .path()
+        .join("worktrees")
+        .join("feature")
+        .join("tidy");
+
+    let _dirty = client
+        .spawn_session(&CreateSessionRequest {
+            cwd: dirty_repo.path().to_path_buf(),
+            command: "sh -c 'echo unsaved > scratch.txt'".into(),
+            env: HashMap::new(),
+            metadata: HashMap::new(),
+            worktree: Some(worktree_spec(dirty_repo.path(), "feature/messy", true)),
+        })
+        .await
+        .expect("spawn dirty");
+    let _pristine = client
+        .spawn_session(&create_req_cmd(
+            pristine_repo.path(),
+            "true",
+            "feature/tidy",
+        ))
+        .await
+        .expect("spawn pristine");
+
+    assert!(dirty_wt.is_dir() && pristine_wt.is_dir());
+
+    // The watcher reaps dead tmux sessions every couple of ticks and settles
+    // each worktree accordingly. Poll for both outcomes.
+    wait_for_async(
+        "dirty exit retains its worktree",
+        Duration::from_secs(20),
+        || {
+            let client = client.clone();
+            let path = dirty_wt.clone();
+            async move {
+                client
+                    .list_worktrees()
+                    .await
+                    .ok()
+                    .map(|wts| {
+                        wts.iter().any(|w| {
+                            w.path == path
+                                && w.reason
+                                    == maestro_protocol::RetainedReason::ExitedWithUnsavedWork
+                        })
+                    })
+                    .unwrap_or(false)
+            }
+        },
+    )
+    .await;
+    wait_for_async(
+        "pristine exit removes its worktree entirely",
+        Duration::from_secs(20),
+        || {
+            let client = client.clone();
+            let repo = pristine_repo.path().to_path_buf();
+            let path = pristine_wt.clone();
+            async move {
+                if path.exists() {
+                    return false;
+                }
+                let listed = client.list_worktrees().await.ok();
+                let listed_clear = listed
+                    .map(|wts| !wts.iter().any(|w| w.path == path))
+                    .unwrap_or(false);
+                let registered = git_worktree_list(&repo);
+                !registered.iter().any(|l| l.contains("feature/tidy")) && listed_clear
+            }
+        },
+    )
+    .await;
+
+    // The dirty tree is still fully there, file included.
+    assert!(dirty_wt.is_dir());
+    assert_eq!(
+        std::fs::read(dirty_wt.join("scratch.txt")).unwrap(),
+        b"unsaved\n"
+    );
+}
+
+fn create_req_cmd(cwd: &std::path::Path, command: &str, branch: &str) -> CreateSessionRequest {
+    CreateSessionRequest {
+        cwd: cwd.to_path_buf(),
+        command: command.into(),
+        env: HashMap::new(),
+        metadata: HashMap::new(),
+        worktree: Some(worktree_spec(cwd, branch, true)),
+    }
+}
+
+/// #80/#88: `GET /api/worktrees` lists what the daemon is holding, with the
+/// reason and a live in-the-way breakdown; reclaim removes the directory and
+/// the store entry but NEVER the branch — its commits outlive the reclaim.
+#[tokio::test(flavor = "multi_thread")]
+async fn worktrees_endpoint_lists_reasons_and_reclaim_keeps_the_branch() {
+    let (_daemon, client) = bring_up().await;
+
+    let base = TempDir::new().unwrap();
+    init_repo(base.path());
+    let _origin = throwaway_origin(base.path());
+
+    let wt = base.path().join("worktrees").join("feature").join("parked");
+    let s = client
+        .spawn_session(&worktree_req(base.path(), "feature/parked", true))
+        .await
+        .expect("spawn");
+    std::fs::write(wt.join("README"), b"worth keeping\n").unwrap();
+    commit_all(&wt, "worth keeping");
+    let sha = branch_sha(&wt, "feature/parked");
+
+    let outcome = client.kill_session_forced(s.id).await.expect("force kill");
+    assert!(outcome.retained.is_some());
+
+    let listed = client.list_worktrees().await.expect("list worktrees");
+    assert_eq!(listed.len(), 1, "exactly one retained entry: {listed:?}");
+    let entry = &listed[0];
+    assert_eq!(entry.path, wt);
+    assert_eq!(entry.branch, "feature/parked");
+    assert_eq!(entry.reason, maestro_protocol::RetainedReason::ForceKilled);
+    assert_eq!(entry.in_the_way.unpushed_commits, 1);
+
+    client.reclaim_worktree(entry.id).await.expect("reclaim");
+    assert!(!wt.exists(), "reclaim removes the directory");
+    assert!(
+        client.list_worktrees().await.unwrap().is_empty(),
+        "reclaim drops the store entry"
+    );
+
+    // The whole point of reclaim: the branch and its commits survive.
+    assert_eq!(
+        branch_sha(base.path(), "feature/parked"),
+        sha,
+        "the branch must keep pointing at the same commit after reclaim"
+    );
+}
+
+/// The retained store is state-dir backed (#80): a daemon restart must not
+/// orphan the trees it is holding — they are still on disk with entries
+/// pointing at them, and still reclaimable afterwards.
+#[tokio::test(flavor = "multi_thread")]
+async fn retained_store_survives_a_daemon_restart() {
+    let (mut daemon, client) = bring_up().await;
+
+    let base = TempDir::new().unwrap();
+    init_repo(base.path());
+    let _origin = throwaway_origin(base.path());
+
+    let wt = base
+        .path()
+        .join("worktrees")
+        .join("feature")
+        .join("durable");
+    let s = client
+        .spawn_session(&worktree_req(base.path(), "feature/durable", true))
+        .await
+        .expect("spawn");
+    std::fs::write(wt.join("README"), b"survives restarts\n").unwrap();
+    commit_all(&wt, "survives restarts");
+    client.kill_session_forced(s.id).await.expect("force kill");
+
+    daemon.restart().await;
+
+    let listed = client.list_worktrees().await.expect("list after restart");
+    assert_eq!(listed.len(), 1, "store must survive restart: {listed:?}");
+    assert_eq!(listed[0].path, wt);
+    assert_eq!(
+        listed[0].reason,
+        maestro_protocol::RetainedReason::ForceKilled
+    );
+    assert!(wt.is_dir(), "the tree itself must survive the restart too");
+
+    client
+        .reclaim_worktree(listed[0].id)
+        .await
+        .expect("reclaim");
+    assert!(!wt.exists());
+}
+
 // ---------------------------------------------------------------------------
 // GET /api/projects + /api/branches (#54/#55/#66)
 // ---------------------------------------------------------------------------
@@ -788,10 +1251,12 @@ fn git_worktree_list(dir: &std::path::Path) -> Vec<String> {
         .collect()
 }
 
-/// Push every branch of `repo` to a throwaway bare remote, so its commits are
-/// reachable from remote-tracking refs. Without one the kill guard (#79)
-/// reads every commit as unpushed, and any worktree session refuses to die.
-fn push_to_throwaway_origin(repo: &std::path::Path) {
+/// Bare remote registered as `origin` on `repo`, seeded with every current
+/// branch, so existing commits are reachable from remote-tracking refs.
+/// Without one the kill guard (#79) reads every commit as unpushed, and any
+/// worktree session refuses to die. The caller must keep the `TempDir` alive
+/// while the remote is still needed; later pushes go through [`push_all`].
+fn throwaway_origin(repo: &std::path::Path) -> TempDir {
     let origin = tempfile::TempDir::new().unwrap();
     run_git(
         &["init", "-q", "--bare", origin.path().to_str().unwrap()],
@@ -803,9 +1268,34 @@ fn push_to_throwaway_origin(repo: &std::path::Path) {
         .args(["remote", "add", "origin", origin.path().to_str().unwrap()])
         .output()
         .expect("git remote add");
+    push_all(repo);
+    origin
+}
+
+fn push_all(repo: &std::path::Path) {
     run_git(&["push", "-q", "--all", "origin"], repo);
 }
 
+fn commit_all(dir: &std::path::Path, message: &str) {
+    run_git(&["add", "-A"], dir);
+    run_git(&["commit", "-q", "-m", message], dir);
+}
+
+fn branch_sha(repo: &std::path::Path, branch: &str) -> String {
+    let out = Command::new("git")
+        .arg("-C")
+        .arg(repo)
+        .args(["rev-parse", "--verify", &format!("refs/heads/{branch}")])
+        .output()
+        .expect("git rev-parse");
+    assert!(
+        out.status.success(),
+        "branch {branch} missing: {}",
+        String::from_utf8_lossy(&out.stderr)
+    );
+    String::from_utf8_lossy(&out.stdout).trim().to_string()
+}
+
 #[tokio::test(flavor = "multi_thread")]
 async fn daemon_events_ws_streams_snapshot_then_session_added() {
     // NAP-248: subscribe to the daemon's WS /api/events, expect an initial

crates/maestro-protocol/src/lib.rs

@@ -119,6 +119,11 @@ pub enum ActivityState {
 pub struct WorktreeSpec {
     pub base_repo: PathBuf,
     pub branch: String,
+    /// Kept on the wire for CLI compatibility (#56) but no longer a
+    /// user-facing choice: the daemon always cleans up on kill, guarded
+    /// against unsaved work. Defaults to `true`.
+    #[serde(default = "default_true")]
+    pub cleanup_on_kill: bool,
     /// When false, `branch` must already exist and is checked out as-is
     /// (#56); when true (the default, and what every payload meant before
     /// the field existed) the daemon creates it with `worktree add -b`.
@@ -589,6 +594,7 @@ mod tests {
             worktree: Some(WorktreeSpec {
                 base_repo: PathBuf::from("/home/naps62/projects/maestro"),
                 branch: "feat/foo".into(),
+                cleanup_on_kill: true,
                 create_branch: true,
             }),
         };
@@ -618,6 +624,7 @@ mod tests {
         });
         let spec: WorktreeSpec = serde_json::from_value(json).unwrap();
         assert!(spec.create_branch);
+        assert!(spec.cleanup_on_kill);
     }
 
     #[test]
@@ -625,6 +632,7 @@ mod tests {
         let spec = WorktreeSpec {
             base_repo: PathBuf::from("/work"),
             branch: "feat/foo".into(),
+            cleanup_on_kill: true,
             create_branch: false,
         };
         assert_eq!(spec, round_trip(&spec));

crates/maestro-tui/src/draft.rs

@@ -549,6 +549,7 @@ impl DraftPane {
                 WorktreeSpec {
                     base_repo,
                     branch: branch.to_string(),
+                    cleanup_on_kill: true,
                     create_branch: true,
                 }
             }
@@ -561,6 +562,7 @@ impl DraftPane {
                 WorktreeSpec {
                     base_repo,
                     branch: name,
+                    cleanup_on_kill: true,
                     create_branch: false,
                 }
             }
@@ -1687,6 +1689,7 @@ mod tests {
         assert_eq!(wt.base_repo, PathBuf::from("/repos/maestro"));
         assert_eq!(wt.branch, "crimson-otter", "branch defaults to the name");
         assert!(wt.create_branch);
+        assert!(wt.cleanup_on_kill);
     }
 
     #[test]

crates/maestro-tui/src/fast_forward.rs

@@ -80,6 +80,7 @@ impl FastForwardDefaults {
                     .clone()
                     .unwrap_or_else(|| project.path.clone()),
                 branch: name.to_string(),
+                cleanup_on_kill: true,
                 create_branch: true,
             }),
         })

docs/WORKTREES.md

@@ -97,6 +97,17 @@ Nobody is waiting for an answer here, so there is nothing to refuse; the choice
 only between removing and retaining. It uses the same predicate as the kill, from
 the same place, so the two paths cannot drift apart.
 
+The session itself stays in the catalog marked dead until it is dismissed — the
+replay buffer of a crashed agent outlives it — but its worktree is settled at
+once. Once settled, the session drops its worktree reference, so dismissing it
+afterwards neither refuses (there is no guard left to trip) nor records a second
+store entry.
+
+If settling is impossible — the probe fails, or the store cannot take the entry —
+nothing is destroyed. The tree stays on disk *and* stays attached to the dead
+record, where dismissing it later still goes through `--force`'s
+retain-before-teardown path. Losing the store must never mean losing the work.
+
 ## The retained store
 
 A `state_dir`-backed record of worktrees the daemon created that no longer have a

web/src/fastForward.test.ts

@@ -43,6 +43,7 @@ describe("resolveFastForward (#67)", () => {
     expect(req.worktree).toEqual({
       base_repo: "/repos/fresh",
       branch: "amber-falcon",
+      cleanup_on_kill: true,
       create_branch: true,
     });
   });

web/src/fastForward.ts

@@ -42,6 +42,7 @@ export function buildFastForwardRequest(
     worktree: {
       base_repo: project.base_repo ?? project.path,
       branch: name,
+      cleanup_on_kill: true,
       create_branch: true,
     },
   };

web/src/spawnForm.test.ts

@@ -38,6 +38,7 @@ describe("buildSpawnRequest", () => {
         worktree: {
           base_repo: "/home/user/project",
           branch: "feat/foo",
+          cleanup_on_kill: true,
           create_branch: true,
         },
       },
@@ -62,6 +63,7 @@ describe("buildSpawnRequest", () => {
         worktree: {
           base_repo: "/home/user/project",
           branch: "spawn-v2",
+          cleanup_on_kill: true,
           create_branch: false,
         },
       },

web/src/spawnForm.ts

@@ -75,6 +75,9 @@ export function buildSpawnRequest(
     req.worktree = {
       base_repo: baseRepo,
       branch,
+      // The daemon always cleans up, guarded against unsaved work (#56);
+      // the wire field stays for older daemons.
+      cleanup_on_kill: true,
       // Existing-mode picks must check out as-is; the daemon creates
       // anything else with `worktree add -b` (#56/#61).
       create_branch: mode !== "existing",

web/src/types.ts

@@ -113,6 +113,7 @@ export type Projects = Project[];
 export interface WorktreeSpec {
   base_repo: string;
   branch: string;
+  cleanup_on_kill?: boolean;
   /** When false, `branch` already exists and is checked out as-is (#61).
    * Defaults to true (create a new branch) on older daemons. */
   create_branch?: boolean;