diff --git a/crates/maestro-tui/src/draft.rs b/crates/maestro-tui/src/draft.rs
index 8f5cf96..31e84c9 100644
--- a/crates/maestro-tui/src/draft.rs
+++ b/crates/maestro-tui/src/draft.rs
@@ -1926,6 +1926,131 @@ mod tests {
         assert_eq!(draft.build_request().unwrap().view, SessionView::Terminal);
     }
 
+    /// A custom command typed into the free-text field, run through the same
+    /// resolver the daemon/web gate uses (`command_tool`, #199): a path, an
+    /// env prefix, or a wrapper still resolves to Claude, so the toggle stays
+    /// offered and the request carries `Structured`; an unrelated program
+    /// does not.
+    #[test]
+    fn structured_view_follows_command_resolution_for_custom_commands() {
+        let cases: &[(&str, bool)] = &[
+            ("claude", true),
+            ("claude --resume", true),
+            ("CLAUDE", true),
+            ("/usr/local/bin/claude -p hi", true),
+            ("./bin/claude", true),
+            ("FOO=1 BAR=2 claude", true),
+            ("npx claude-code", true),
+            ("sudo claude", true),
+            ("bash", false),
+            ("opencode", false),
+            ("/usr/local/bin/bash -l", false),
+        ];
+        for &(command, supported) in cases {
+            let mut draft = DraftPane {
+                picked_cwd: Some(PathBuf::from("/srv/work")),
+                worktree_enabled: false,
+                advanced_collapsed: false,
+                ..DraftPane::default()
+            };
+            draft.selected_preset = draft.presets.len() - 1;
+            draft.custom_command = crate::text_input::TextInput::with_value(command);
+
+            assert_eq!(
+                draft.field_order().contains(&DraftField::StructuredToggle),
+                supported,
+                "toggle visibility for {command:?}"
+            );
+            draft.toggle_structured_view();
+            assert_eq!(
+                draft.structured_view, supported,
+                "toggle takes effect for {command:?}"
+            );
+            let view = draft.build_request().unwrap().view;
+            assert_eq!(
+                view,
+                if supported {
+                    SessionView::Structured
+                } else {
+                    SessionView::Terminal
+                },
+                "request view for {command:?}"
+            );
+        }
+    }
+
+    /// A configured preset (the spawn-form "alias" for a command) is gated
+    /// the same way as free text: a preset whose command resolves to Claude
+    /// through a wrapper still offers structured view.
+    #[test]
+    fn structured_view_follows_command_resolution_for_presets() {
+        let mut draft = DraftPane {
+            picked_cwd: Some(PathBuf::from("/srv/work")),
+            worktree_enabled: false,
+            advanced_collapsed: false,
+            ..DraftPane::default()
+        };
+        draft.set_presets(vec![
+            SpawnPreset {
+                id: "claude-wrapped".into(),
+                label: "Claude (npx)".into(),
+                command: "npx claude-code --resume".into(),
+            },
+            SpawnPreset {
+                id: "aider".into(),
+                label: "Aider".into(),
+                command: "aider".into(),
+            },
+        ]);
+
+        assert_eq!(draft.command(), "npx claude-code --resume");
+        assert!(draft.field_order().contains(&DraftField::StructuredToggle));
+        draft.toggle_structured_view();
+        assert!(draft.structured_view);
+        assert_eq!(draft.build_request().unwrap().view, SessionView::Structured);
+
+        // Switching to a preset that does not resolve to Claude clears the
+        // stale selection instead of letting an invalid request through.
+        draft.cycle_preset(1);
+        assert_eq!(draft.command(), "aider");
+        assert!(!draft.structured_view, "stale selection must clear");
+        assert!(!draft.field_order().contains(&DraftField::StructuredToggle));
+        assert_eq!(draft.build_request().unwrap().view, SessionView::Terminal);
+    }
+
+    /// Editing the custom-command text away from Claude clears an armed
+    /// selection immediately, matching the preset-switch case above — an
+    /// invalid `Structured` request can never reach `build_request`.
+    #[test]
+    fn structured_view_clears_when_custom_command_edited_away_from_claude() {
+        let mut draft = DraftPane {
+            picked_cwd: Some(PathBuf::from("/srv/work")),
+            worktree_enabled: false,
+            advanced_collapsed: false,
+            focused_field: DraftField::CustomCommand,
+            ..DraftPane::default()
+        };
+        draft.selected_preset = draft.presets.len() - 1;
+        draft.custom_command = crate::text_input::TextInput::with_value("claude");
+        draft.toggle_structured_view();
+        assert!(draft.structured_view);
+
+        typed(&mut draft, " -p");
+        assert_eq!(draft.command(), "claude -p");
+        assert!(draft.structured_view, "still Claude, selection survives");
+
+        for _ in 0.."claude -p".chars().count() {
+            draft.on_input(&InputKey::Backspace);
+        }
+        typed(&mut draft, "bash");
+        assert_eq!(draft.command(), "bash");
+        assert!(
+            !draft.structured_view,
+            "editing the program away from claude clears the stale selection"
+        );
+        assert_eq!(draft.build_request().unwrap().view, SessionView::Terminal);
+    }
+
     #[test]
     fn projects_render_sorted_with_stale_dimmed_and_other_directory_last() {
         let mut draft = DraftPane {