diff --git a/ROADMAP.md b/ROADMAP.md
index 171c129..f826a37 100644
--- a/ROADMAP.md
+++ b/ROADMAP.md
@@ -2,7 +2,7 @@
 
 **Stage: pre-alpha** · next: alpha, ~0% and ~15–25 h away; beta ~28 points and ~420–750 h beyond that (the core-workflow gate, not the percentage: ready for real work is already ~47%)
 
-> **Last reviewed:** 2026-10-10 · **Last updated:** 2026-10-12 · **Change:** minor (recovery checkpoint retention) · **Target:** Adobe InDesign 2026
+> **Last reviewed:** 2026-10-10 · **Last updated:** 2026-10-12 · **Change:** minor (orderly native exit recovery) · **Target:** Adobe InDesign 2026
 
 DesignCraft aims at full Adobe InDesign parity, and to be better: faster, open (documented JSON
 format + IDML), scriptable by agents (MCP), and available on the web.
@@ -129,6 +129,7 @@ list) · [roadmap.md](docs/roadmap.md) (milestones, plan) · [parity-checklist.m
 
 Newest first.
 
+- **2026-10-12** · Orderly native exit writes the latest recovery state after finalizing current quit approvals; incomplete or stale plans keep their documents, and Undo to the saved state clears stale recovery. Unavailable or failed recovery is reported. Cancelable macOS Dock Quit remains open (#544). No readiness percentage change.
 - **2026-10-12** · Recovered documents keep a checkpoint until saved, closed or reverted, including a second crash before autosave. Restarted document IDs and explicit recovery folders preserve other snapshots; failed republishing retains the original. No readiness percentage change.
 - **2026-10-12** · Book numbering and style updates prepare every chapter before saving. Only closed native chapters are changed; imported IDML remains a read-only style/PDF source. If a later disk write fails, the error names the completed chapters; the batch is not a whole-book transaction. No readiness percentage change.
 - **2026-10-12** · Desktop write callbacks and CLI raster exports use the atomic writer too; open readers retain the original bytes, while private Unix modes and symlink targets survive replacement. Permanent tests cover both actual callers. No readiness percentage change.
diff --git a/apps/designcraft/src/main.rs b/apps/designcraft/src/main.rs
index e3ff86c..f468125 100644
--- a/apps/designcraft/src/main.rs
+++ b/apps/designcraft/src/main.rs
@@ -64,10 +64,33 @@ impl eframe::App for App {
         if let Some(s) = self.startup.as_mut() {
             s.presented();
         }
+        if let Err(e) = preserve_documents_on_exit(&mut self.app) {
+            log::error!("Couldn't preserve documents on exit: {e}");
+            eprintln!("designcraft: couldn't preserve documents on exit: {e}");
+        }
         save_prefs(&self.app);
     }
 }
 
+/// Orderly OS termination can bypass egui's cancelable close event. Finish only a complete,
+/// current quit plan; otherwise preserve every live document, including edits after the timer.
+fn preserve_documents_on_exit(app: &mut DesignApp) -> Result<(), String> {
+    app.finish_confirmed_quit()?;
+    if app.session.documents().is_empty() {
+        return Ok(());
+    }
+    if app.session.recovery_dir.is_none() {
+        return if app.session.documents().iter().any(|d| d.is_dirty()) {
+            Err("Recovery is unavailable; unsaved documents could not be preserved on exit".into())
+        } else {
+            Ok(())
+        };
+    }
+    // Also discard stale recovery for clean documents (for example, Undo back to the saved
+    // state after the last timer tick). Never choose a fallback recovery path here.
+    app.run("file.recovery.save", serde_json::json!({})).map(|_| ())
+}
+
 /// `DESIGNCRAFT_NO_PREFS`: read and write nothing in the settings directory (tests, demos).
 fn no_prefs() -> bool {
     std::env::var_os("DESIGNCRAFT_NO_PREFS").is_some()
@@ -387,3 +410,134 @@ mod atomic_writer_tests {
         assert!(std::fs::symlink_metadata(alias).unwrap().file_type().is_symlink());
     }
 }
+
+#[cfg(test)]
+mod exit_recovery_tests {
+    use super::*;
+    use serde_json::json;
+
+    fn dirty_app(label: &str) -> (DesignApp, std::path::PathBuf) {
+        let mut app = DesignApp::new(Session::new(), Services::default());
+        app.run("file.new", json!({})).unwrap();
+        app.run("frame.create", json!({"rect": [20, 20, 120, 120]})).unwrap();
+        let uid = app.session.active().unwrap().uid;
+        let dir = std::env::temp_dir().join(format!("designcraft-exit-{label}-{}-{uid}", std::process::id()));
+        assert!(!dir.exists());
+        app.session.recovery_dir = Some(dir.clone());
+        (app, dir)
+    }
+
+    fn close_frame(app: &mut DesignApp, ctx: &egui::Context, close: bool) {
+        let mut raw = egui::RawInput::default();
+        if close {
+            raw.viewports.entry(egui::ViewportId::ROOT).or_default().events.push(egui::ViewportEvent::Close);
+        }
+        let mut out = ctx.run_ui(raw, |ui| app.logic(ui.ctx()));
+        out.textures_delta.clear();
+    }
+
+    #[test]
+    fn exit_recovery_preserves_latest_dirty_document_without_mutating_it() {
+        let (mut app, dir) = dirty_app("latest");
+        app.run("file.recovery.save", json!({})).unwrap();
+        app.run("frame.create", json!({"rect": [200, 200, 300, 300]})).unwrap();
+        let d = app.session.active().unwrap();
+        let (uid, revision, saved_revision, doc, selection, undo, redo) =
+            (d.uid, d.revision, d.saved_revision, d.doc.clone(), d.selection.items.clone(), d.history.undo.len(), d.history.redo.len());
+        preserve_documents_on_exit(&mut app).unwrap();
+        let current = app.session.active().unwrap();
+        assert_eq!(
+            (current.uid, current.revision, current.saved_revision, &current.selection.items, current.history.undo.len(), current.history.redo.len()),
+            (uid, revision, saved_revision, &selection, undo, redo)
+        );
+        assert!(std::sync::Arc::ptr_eq(&current.doc, &doc));
+        assert!(current.is_dirty());
+        let recovered = designcraft_engine::cmd::from_bytes(&std::fs::read(dir.join(format!("{uid}.designcraft"))).unwrap()).unwrap();
+        assert_eq!(serde_json::to_value(&recovered).unwrap(), serde_json::to_value(doc.as_ref()).unwrap());
+        std::fs::remove_dir_all(dir).unwrap();
+    }
+
+    #[test]
+    fn exit_recovery_removes_stale_data_after_undo_to_saved_state() {
+        let (mut app, dir) = dirty_app("clean");
+        let uid = app.session.active().unwrap().uid;
+        app.run("file.recovery.save", json!({})).unwrap();
+        let entry = dir.join(format!("{uid}.designcraft"));
+        assert!(entry.exists());
+        app.run("edit.undo", json!({})).unwrap();
+        assert!(!app.session.active().unwrap().is_dirty());
+        let doc = app.session.active().unwrap().doc.clone();
+        preserve_documents_on_exit(&mut app).unwrap();
+        assert!(!entry.exists(), "clean exit must not resurrect the pre-Undo edits");
+        assert!(std::sync::Arc::ptr_eq(&app.session.active().unwrap().doc, &doc));
+        std::fs::remove_dir_all(dir).unwrap();
+    }
+
+    #[test]
+    fn exit_recovery_reports_unavailable_or_failed_storage_without_changing_documents() {
+        let (mut app, dir) = dirty_app("failure");
+        let doc = app.session.active().unwrap().doc.clone();
+        app.session.recovery_dir = None;
+        assert!(preserve_documents_on_exit(&mut app).unwrap_err().contains("unavailable"));
+        std::fs::create_dir(&dir).unwrap();
+        let blocked = dir.join("not-a-directory");
+        std::fs::write(&blocked, b"preserve this file").unwrap();
+        app.session.recovery_dir = Some(blocked.clone());
+        assert!(preserve_documents_on_exit(&mut app).is_err());
+        assert_eq!(std::fs::read(&blocked).unwrap(), b"preserve this file");
+        assert!(std::sync::Arc::ptr_eq(&app.session.active().unwrap().doc, &doc));
+        assert!(app.session.active().unwrap().is_dirty());
+        assert_eq!(app.session.documents().len(), 1);
+        std::fs::remove_dir_all(dir).unwrap();
+    }
+
+    #[test]
+    fn exit_recovery_respects_complete_incomplete_stale_and_new_document_quit_plans() {
+        for case in ["complete", "incomplete", "stale", "new"] {
+            let (mut app, dir) = dirty_app(case);
+            if case == "incomplete" {
+                app.run("file.new", json!({})).unwrap();
+                app.run("frame.create", json!({"rect": [20, 20, 120, 120]})).unwrap();
+            }
+            app.run("file.recovery.save", json!({})).unwrap();
+            let first_uid = app.session.documents()[0].uid;
+            let ctx = egui::Context::default();
+            close_frame(&mut app, &ctx, true);
+            app.ui.dialog.as_mut().unwrap().fields.insert("discard".into(), json!(true));
+            designcraft_ui_egui::dialogs::confirm(&mut app).unwrap();
+            close_frame(&mut app, &ctx, false);
+            if case == "stale" {
+                app.run("frame.create", json!({"rect": [200, 200, 300, 300]})).unwrap();
+            } else if case == "new" {
+                app.run("file.new", json!({})).unwrap();
+                app.run("frame.create", json!({"rect": [20, 20, 120, 120]})).unwrap();
+            }
+            let active = app.session.active().unwrap().uid;
+            let before: Vec<_> = app
+                .session
+                .documents()
+                .iter()
+                .map(|d| (d.uid, d.revision, d.doc.clone(), d.selection.items.clone(), d.history.undo.len(), d.history.redo.len()))
+                .collect();
+            preserve_documents_on_exit(&mut app).unwrap();
+            if case == "complete" {
+                assert!(app.session.documents().is_empty());
+                assert!(!dir.join(format!("{first_uid}.designcraft")).exists(), "accepted Don't Save must not be recovered");
+            } else {
+                assert_eq!(app.session.documents().len(), before.len(), "{case}");
+                assert_eq!(app.session.active().unwrap().uid, active, "{case}");
+                for (d, (uid, revision, doc, selection, undo, redo)) in app.session.documents().iter().zip(before) {
+                    assert_eq!(
+                        (d.uid, d.revision, &d.selection.items, d.history.undo.len(), d.history.redo.len()),
+                        (uid, revision, &selection, undo, redo),
+                        "{case}"
+                    );
+                    assert!(std::sync::Arc::ptr_eq(&d.doc, &doc), "{case}");
+                    let recovered = designcraft_engine::cmd::from_bytes(&std::fs::read(dir.join(format!("{uid}.designcraft"))).unwrap()).unwrap();
+                    assert_eq!(serde_json::to_value(&recovered).unwrap(), serde_json::to_value(doc.as_ref()).unwrap(), "{case}");
+                }
+            }
+            std::fs::remove_dir_all(dir).unwrap();
+        }
+    }
+}
diff --git a/docs/architecture.md b/docs/architecture.md
index 4f06fbc..be3274b 100644
--- a/docs/architecture.md
+++ b/docs/architecture.md
@@ -1,6 +1,6 @@
 # DesignCraft architecture
 
-> **Last reviewed:** 2026-10-10 · **Last updated:** 2026-10-10 · **Change:** major (first committed version, from the code on main and the local plan) · **Target:** Adobe InDesign 2026
+> **Last reviewed:** 2026-10-10 · **Last updated:** 2026-10-12 · **Change:** minor (orderly native exit recovery) · **Target:** Adobe InDesign 2026
 
 How DesignCraft is built today. The design notes behind it are in `plan/architecture.md`
 (local, gitignored); this file describes what the code on `main` does. Agents: AGENTS.md has the
@@ -57,8 +57,11 @@ and the control channel all call `Session::execute(id, params)`. UI-only command
 panels, zoom, dialogs) are `UI_COMMANDS` in `crates/ui-egui/src/menus.rs`, reachable the same way.
 Tool gestures emit Begin/Preview/Commit commands so a drag is one undo step. Every journaled
 command is replayable as a script. Escaped panics during a command or an import/export become an
-error (`engine/src/guard.rs`), never a lost document; unsaved documents are written to a recovery
-folder every 30 s.
+error (`engine/src/guard.rs`), never a lost document; native recovery is written periodically
+into each running app's locked folder. Orderly native shutdown finalizes complete, current quit
+approvals and writes the remaining documents' latest recovery state, including clean-document
+cleanup after Undo. Unavailable or failed recovery is reported. Cancelable macOS Dock Quit
+remains open (#544).
 
 ## Composition and rendering
 
@@ -95,4 +98,5 @@ builds (on manifest changes), packaging lint and the release workflow; `xtask ci
 
 | Date | Change | Summary |
 |---|---|---|
+| 2026-10-12 | minor | Documented orderly native exit recovery and the remaining cancelable Dock Quit gap |
 | 2026-10-10 | major | Created from the code on main (92649ff) and `plan/architecture.md` |