diff --git a/services/web/frontend/js/features/ide-react/editor/offline-doc-backup.ts b/services/web/frontend/js/features/ide-react/editor/offline-doc-backup.ts
index e687870375..d39ff42764 100644
--- a/services/web/frontend/js/features/ide-react/editor/offline-doc-backup.ts
+++ b/services/web/frontend/js/features/ide-react/editor/offline-doc-backup.ts
@@ -8,6 +8,7 @@ import { IdeEventEmitter } from '@/features/ide-react/create-ide-event-emitter'
 const EVENT_NAMESPACE = 'offlineBackup'
 const OFFLINE_BACKUP_INTERVAL_MS = 2000
 const KEY_PREFIX = 'doc.offline-backup.'
+const STALL_AFTER_SECONDS = 10
 
 type Baseline = {
   version: number
@@ -101,6 +102,20 @@ export class OfflineDocBackup {
     return this.doc.connection.state !== 'ok'
   }
 
+  private isSavingStalled() {
+    const oldestOpCreatedAt =
+      this.doc.getInflightOpCreatedAt() ?? this.doc.getPendingOpCreatedAt()
+    if (!oldestOpCreatedAt) {
+      return false
+    }
+    const unsavedSeconds = (performance.now() - oldestOpCreatedAt) / 1000
+    return unsavedSeconds > STALL_AFTER_SECONDS
+  }
+
+  private shouldBackup() {
+    return this.isOffline() || this.isSavingStalled()
+  }
+
   private refreshBaseline() {
     // baseline is the clean server state, buffered ops would
     // bake local edits into V_start and corrupt recovery
@@ -144,7 +159,7 @@ export class OfflineDocBackup {
     // reflects remote ops applied before we go offline. refreshBaseline no-ops
     // once there are buffered ops, freezing the baseline at the point we start
     // diverging offline.
-    if (!this.isOffline()) {
+    if (!this.shouldBackup()) {
       this.refreshBaseline()
       return
     }
@@ -156,7 +171,7 @@ export class OfflineDocBackup {
     }
     this.throttleTimer = window.setTimeout(() => {
       this.throttleTimer = null
-      if (this.isOffline() && this.doc.hasBufferedOps()) {
+      if (this.shouldBackup() && this.doc.hasBufferedOps()) {
         this.write()
       }
     }, OFFLINE_BACKUP_INTERVAL_MS)
diff --git a/services/web/test/frontend/features/ide-react/unit/editor/offline-doc-backup.test.ts b/services/web/test/frontend/features/ide-react/unit/editor/offline-doc-backup.test.ts
index 2764fcf29b..1385eb93f9 100644
--- a/services/web/test/frontend/features/ide-react/unit/editor/offline-doc-backup.test.ts
+++ b/services/web/test/frontend/features/ide-react/unit/editor/offline-doc-backup.test.ts
@@ -15,6 +15,7 @@ const PROJECT_ID = 'project-456'
 const USER_ID = 'user-789'
 const KEY = `doc.offline-backup.${USER_ID}.${PROJECT_ID}.${DOC_ID}`
 const FLUSH_DELAY = 2000
+const STALL_AFTER_MS = 10000
 const SYNCED_EVENT = 'ide:offlineChangesSynced'
 
 class FakeShareJsDoc extends EventEmitter {
@@ -27,6 +28,8 @@ class FakeShareJsDoc extends EventEmitter {
   snapshot = 'server text'
   inflightOp: ShareJsOperation | null = null
   pendingOp: ShareJsOperation | null = null
+  inflightOpCreatedAt: number | null = null
+  pendingOpCreatedAt: number | null = null
   track_changes = false
   otType: OTType = 'sharejs-text-ot'
   _doc = { inflightSubmittedIds: new Set<string>() }
@@ -60,6 +63,14 @@ class FakeShareJsDoc extends EventEmitter {
     return this.pendingOp
   }
 
+  getInflightOpCreatedAt() {
+    return this.inflightOpCreatedAt
+  }
+
+  getPendingOpCreatedAt() {
+    return this.pendingOpCreatedAt
+  }
+
   getInflightSubmittedIds() {
     return this._doc.inflightSubmittedIds
   }
@@ -151,6 +162,41 @@ describe('OfflineDocBackup', function () {
     expect(readRecord()).to.be.null
   })
 
+  it('backs up while still connected once saving stalls past the threshold', function () {
+    create()
+    doc.pendingOp = [{ i: 'x', p: 0 }]
+    doc.pendingOpCreatedAt = performance.now() - (STALL_AFTER_MS + 1000)
+    doc.trigger('change')
+    clock.tick(FLUSH_DELAY)
+
+    expect(doc.connection.state).to.equal('ok')
+    expect(readRecord()?.pendingOp).to.deep.equal([{ i: 'x', p: 0 }])
+  })
+
+  it('does not back up while connected and within the stall threshold', function () {
+    create()
+    doc.pendingOp = [{ i: 'x', p: 0 }]
+    doc.pendingOpCreatedAt = performance.now() - (STALL_AFTER_MS - 5000)
+    doc.trigger('change')
+    clock.tick(FLUSH_DELAY)
+
+    expect(readRecord()).to.be.null
+  })
+
+  it('uses the inflight op age (the oldest) to detect a stall', function () {
+    create()
+    doc.inflightOp = [{ i: 'sent', p: 0 }]
+    doc.inflightOpCreatedAt = performance.now() - (STALL_AFTER_MS + 1000)
+    doc.pendingOp = [{ i: 'queued', p: 5 }]
+    doc.pendingOpCreatedAt = performance.now()
+    doc.trigger('change')
+    clock.tick(FLUSH_DELAY)
+
+    const record = readRecord()
+    expect(record?.inflightOp).to.deep.equal([{ i: 'sent', p: 0 }])
+    expect(record?.pendingOp).to.deep.equal([{ i: 'queued', p: 5 }])
+  })
+
   it('writes the baseline plus live ops when offline with buffered ops', function () {
     create()
     goOffline()