From e278bc9a17b42e9b76ca7cd15a1ae52fcd582cc5 Mon Sep 17 00:00:00 2001
From: Neil <4138956+nwparker@users.noreply.github.com>
Date: Mon, 19 Oct 2026 22:44:43 -0700
Subject: [PATCH] feat(orcad-migration): unsaved drafts stay on this desktop
 and are renamed to the server on commit (#30894)

* feat(orcad-migration): unsaved drafts stay on this desktop and are renamed to the server on commit

* fix(orcad-migration): refuse clashing drafts from the rename's own collection; stricter live spec

* fix(orcad-migration): stamp renamed drafts with the server, rename at startup after a cut-off commit, keep draft refusals

* fix(orcad-migration): retain only after a startup rename is durable; startup survives an unreadable journal

* fix(orcad-migration): a cut-off commit is renamed and retained at startup, so the rename runs once

* fix(orcad-migration): one retain per migration at a time; no rollback that could drop newer edits

* test(e2e): check the visible draft in whichever editor a large file opens in

* fix(orcad-migration): startup retains only migrations of hosts this profile owns

* ci(e2e): route the editor-drafts migration spec to the sources it covers
---
 config/main-layout-writer-baseline.txt        |   1 +
 config/scripts/pr-e2e-source-routing.mjs      |  11 +
 .../ssh/ssh-host-server-on-connect-wiring.ts  |   4 +-
 src/main/ipc/ssh/ssh.ts                       |   2 +
 .../lifecycle/orcad-runtime-conversion.ts     |   2 +-
 .../orcad-source-draft-rename.ts              | 104 ++++++++
 .../orcad-source-export.ts                    |   9 +
 .../orcad-source-release-upgrade.test.ts      |  15 +-
 .../orcad-source-workspace-session.ts         |   9 +-
 .../ssh/orcad-migration-delta-move.test.ts    |   4 +-
 src/main/ssh/orcad-migration-delta-move.ts    |   2 +-
 .../orcad-migration-source-retention.test.ts  | 225 +++++++++++++++++-
 .../ssh/orcad-migration-source-retention.ts   | 143 ++++++++++-
 src/main/ssh/orcad-migration-source.ts        |   2 -
 .../ssh/orcad-migration-ssh-relay-source.ts   |   5 +-
 ...rcad-migration-stuck-host-profiles.test.ts |  56 ++++-
 .../ssh-host-server-on-connect-test-deps.ts   |   2 +-
 src/main/ssh/ssh-host-server-on-connect.ts    |   4 +-
 tests/e2e/helpers/orcad-convert-host.ts       |   7 +
 tests/e2e/helpers/orcad-managed-workspace.ts  |  15 +-
 tests/e2e/helpers/orcad-upgrade-profile.ts    |   5 +-
 .../ssh-orcad-editor-drafts-migration.spec.ts | 216 +++++++++++++++++
 22 files changed, 798 insertions(+), 45 deletions(-)
 create mode 100644 src/main/persistence/migrating-orcad-catalog/orcad-source-draft-rename.ts
 create mode 100644 tests/e2e/ssh-orcad-editor-drafts-migration.spec.ts

diff --git a/config/main-layout-writer-baseline.txt b/config/main-layout-writer-baseline.txt
index a2558f48639..4166afdb39d 100644
--- a/config/main-layout-writer-baseline.txt
+++ b/config/main-layout-writer-baseline.txt
@@ -71,5 +71,6 @@
 4 src/main/runtime/workspace-session-worktree-id.ts
 1 src/main/runtime/workspaces/session-hosts/get-runtime-id.ts
 2 src/main/runtime/workspaces/workspace-file-session-targets.ts
+1 src/main/ssh/orcad-migration-source-retention.ts
 1 src/main/ssh/targets/ssh-target-id-migration.ts
 2 src/main/terminal-scrollback-snapshots.ts
diff --git a/config/scripts/pr-e2e-source-routing.mjs b/config/scripts/pr-e2e-source-routing.mjs
index d0f0bae07b7..156381499ce 100644
--- a/config/scripts/pr-e2e-source-routing.mjs
+++ b/config/scripts/pr-e2e-source-routing.mjs
@@ -253,6 +253,17 @@ export const PR_E2E_SOURCE_ROUTES = [
           file
         ))
   },
+  {
+    // Unsaved drafts stay on the desktop and are renamed to the server when a move commits.
+    id: 'ssh.orcad-editor-drafts-migration',
+    specs: ['tests/e2e/ssh-orcad-editor-drafts-migration.spec.ts'],
+    matches: (file) =>
+      MANAGED_SSH_HARNESS.test(file) ||
+      (isProductSource(file) &&
+        /^src\/main\/(?:persistence\/migrating-orcad-catalog\/orcad-source-(?:draft-rename|workspace-session|session-copy-resolution|export)|ssh\/orcad-migration-source-retention|ipc\/ssh\/ssh)\.ts$/.test(
+          file
+        ))
+  },
   {
     // Why: hand-kept routes missed #30130 and #30120; scoped to managed-host code to bound lane cost.
     id: 'ssh.orcad-remote-sources',
diff --git a/src/main/ipc/ssh/ssh-host-server-on-connect-wiring.ts b/src/main/ipc/ssh/ssh-host-server-on-connect-wiring.ts
index c79d5de4eb8..96fc15bab62 100644
--- a/src/main/ipc/ssh/ssh-host-server-on-connect-wiring.ts
+++ b/src/main/ipc/ssh/ssh-host-server-on-connect-wiring.ts
@@ -55,10 +55,10 @@ export function hostServerOnConnectDeps(userDataPath: string): HostServerOnConne
       await ensureOrcadManagedTunnel(userDataPath, environmentId)
     },
     ensureServing: (environmentId) => verifyOrcadManagedServing(userDataPath, environmentId),
-    retainCommittedSource: (target) => {
+    retainCommittedSource: async (target) => {
       const head = findOrcadMigrationSourceCutoverForTarget(userDataPath, target.id)
       if (head?.phase === 'destination-committed') {
-        retainOrcadMigrationSource(userDataPath, head.migrationId)
+        await retainOrcadMigrationSource(userDataPath, head.migrationId, store)
       }
     },
     hasTemplate: hasOrcadTemplate,
diff --git a/src/main/ipc/ssh/ssh.ts b/src/main/ipc/ssh/ssh.ts
index 53f581cbddb..6206a11a1e4 100644
--- a/src/main/ipc/ssh/ssh.ts
+++ b/src/main/ipc/ssh/ssh.ts
@@ -53,6 +53,7 @@ import { resetSshShutdownDrain } from './ssh-shutdown-drain'
 import { registerSshTargetCrudHandlers } from './ssh-target-crud-handlers'
 import { targetLifecycleInFlight } from './ssh-target-lifecycle-queue'
 import { disposeOrcadManagedTunnels } from '../../managed-server/lifecycle/orcad-managed-tunnel'
+import { retainUnretainedOrcadMigrationSources } from '../../ssh/orcad-migration-source-retention'
 import { reconcileManagedOrcadSshTargets } from '../../ssh/orcad-retained-source'
 import { installOrcadMigrationScrollbackRetention } from '../../ssh/orcad-migration-scrollback-retention-wiring'
 import { getAppEnvironment } from '../../../shared/app-environment'
@@ -99,6 +100,7 @@ export function registerSshHandlers(
   setSshTargetRegistryStore(new SshConnectionStore(store))
   setPersistedStore(store)
   reconcileManagedOrcadSshTargets(getAppEnvironment().getPath('userData'), store)
+  void retainUnretainedOrcadMigrationSources(getAppEnvironment().getPath('userData'), store)
   installOrcadMigrationScrollbackRetention(getAppEnvironment().getPath('userData'), store)
   installManagedOrcadStartStatus()
 
diff --git a/src/main/managed-server/lifecycle/orcad-runtime-conversion.ts b/src/main/managed-server/lifecycle/orcad-runtime-conversion.ts
index e101fec29cc..944bb817d6e 100644
--- a/src/main/managed-server/lifecycle/orcad-runtime-conversion.ts
+++ b/src/main/managed-server/lifecycle/orcad-runtime-conversion.ts
@@ -138,7 +138,7 @@ export async function convertSshTargetToManagedOrcad(
     throw new Error(`orcad_migration_commit_not_proven:${committed.phase}`)
   }
   if (committed.phase === 'destination-committed') {
-    retainOrcadMigrationSource(userDataPath, committed.migrationId, args.now)
+    await retainOrcadMigrationSource(userDataPath, committed.migrationId, store, args.now)
   }
   const linkedProjects = linkedOrcadMigrationProjects(store, linked)
   return {
diff --git a/src/main/persistence/migrating-orcad-catalog/orcad-source-draft-rename.ts b/src/main/persistence/migrating-orcad-catalog/orcad-source-draft-rename.ts
new file mode 100644
index 00000000000..6bf974e7b20
--- /dev/null
+++ b/src/main/persistence/migrating-orcad-catalog/orcad-source-draft-rename.ts
@@ -0,0 +1,104 @@
+/**
+ * Unsaved editor drafts never leave this desktop. Its own session holds each one per host
+ * partition, file path and disk baseline; a committed move renames the record from the SSH host
+ * to its server, and restore lays it over the file and warns when the baseline no longer matches.
+ */
+import type { OrcadMigrationManifest } from '../../../shared/orcad-migration/orcad-migration-manifest'
+import type { PersistedState } from '../../../shared/persisted-state-types'
+import type {
+  PersistedOpenFile,
+  WorkspaceSessionState
+} from '../../../shared/workspace-session-state-types'
+import {
+  createOrcadMigrationSourceScope,
+  orcadMigrationOwnerMatchesScope,
+  orcadMigrationPartitionScope,
+  unqualifyOrcadMigrationOwnerKey
+} from './orcad-source-scope'
+import { orcadMigrationSessionPartitions } from './orcad-source-session-partitions'
+
+/** Destination worktree key → the drafted files it gains, as the server names that worktree. */
+export type OrcadMigrationSourceDrafts = Record<string, PersistedOpenFile[]>
+
+/** Another host's file stays that host's record; the move cannot rename it. */
+export function isHostBoundOpenFile(file: PersistedOpenFile): boolean {
+  return file.externalSshTargetId !== undefined || Boolean(file.runtimeEnvironmentId)
+}
+
+export function collectOrcadMigrationSourceDrafts(
+  state: PersistedState,
+  manifest: Pick<OrcadMigrationManifest, 'source' | 'payload'>
+): OrcadMigrationSourceDrafts {
+  const sourceScope = createOrcadMigrationSourceScope({
+    source: manifest.source,
+    catalog: manifest.payload,
+    repos: state.repos
+  })
+  // The host's own copy first: where both hold one file, it is the one the app reads.
+  const partitions = orcadMigrationSessionPartitions(state, sourceScope).sort(
+    ([a], [b]) => Number(b === sourceScope.hostId) - Number(a === sourceScope.hostId)
+  )
+  const drafts = new Map<string, Map<string, PersistedOpenFile>>()
+  for (const [partitionId, session] of partitions) {
+    const scope = orcadMigrationPartitionScope(sourceScope, partitionId)
+    for (const [ownerKey, files] of Object.entries(session.openFilesByWorktree ?? {})) {
+      if (!orcadMigrationOwnerMatchesScope(ownerKey, scope)) {
+        continue
+      }
+      const key = unqualifyOrcadMigrationOwnerKey(ownerKey)
+      for (const file of files) {
+        if (file.dirtyDraftContent === undefined || isHostBoundOpenFile(file)) {
+          continue
+        }
+        const byPath = drafts.get(key) ?? new Map<string, PersistedOpenFile>()
+        drafts.set(key, byPath)
+        if (!byPath.has(file.filePath)) {
+          byPath.set(file.filePath, { ...structuredClone(file), worktreeId: key })
+        }
+      }
+    }
+  }
+  return Object.fromEntries([...drafts].map(([key, byPath]) => [key, [...byPath.values()]]))
+}
+
+/**
+ * The destination partition with each draft added, or null when nothing changes. A file the
+ * destination already lists keeps its own record, so a draft discarded there never comes back.
+ */
+export function withRenamedOrcadMigrationDrafts(
+  destination: WorkspaceSessionState,
+  drafts: OrcadMigrationSourceDrafts,
+  destinationEnvironmentId: string
+): WorkspaceSessionState | null {
+  const openFilesByWorktree = { ...destination.openFilesByWorktree }
+  let changed = false
+  for (const [key, files] of Object.entries(drafts)) {
+    const held = openFilesByWorktree[key] ?? []
+    const heldPaths = new Set(held.map((file) => file.filePath))
+    // Owned by the server now, so reads, saves and its mirrored tab all resolve to it.
+    const added = files
+      .filter((file) => !heldPaths.has(file.filePath))
+      .map((file) => ({ ...file, runtimeEnvironmentId: destinationEnvironmentId }))
+    if (added.length > 0) {
+      openFilesByWorktree[key] = [...held, ...added]
+      changed = true
+    }
+  }
+  return changed ? { ...destination, openFilesByWorktree } : null
+}
+
+/** The session the server is sent: tabs without their unsaved contents. */
+export function withoutOrcadMigrationDrafts(session: WorkspaceSessionState): WorkspaceSessionState {
+  if (!session.openFilesByWorktree) {
+    return session
+  }
+  return {
+    ...session,
+    openFilesByWorktree: Object.fromEntries(
+      Object.entries(session.openFilesByWorktree).map(([key, files]) => [
+        key,
+        files.map(({ dirtyDraftContent: _draft, lastKnownDiskSignature: _base, ...file }) => file)
+      ])
+    )
+  }
+}
diff --git a/src/main/persistence/migrating-orcad-catalog/orcad-source-export.ts b/src/main/persistence/migrating-orcad-catalog/orcad-source-export.ts
index 55514d3645c..4301a673af2 100644
--- a/src/main/persistence/migrating-orcad-catalog/orcad-source-export.ts
+++ b/src/main/persistence/migrating-orcad-catalog/orcad-source-export.ts
@@ -28,6 +28,10 @@ import {
 } from './orcad-source-delta-view'
 import { syncOrcadMigrationScrollbackRetention } from './orcad-source-scrollback-retention'
 import { createOrcadMigrationLeaveBehindView } from './orcad-source-leave-behind-view'
+import {
+  collectOrcadMigrationSourceDrafts,
+  type OrcadMigrationSourceDrafts
+} from './orcad-source-draft-rename'
 
 type OrcadSourceExportRuntime = Pick<
   StoreRuntimeState,
@@ -58,6 +62,11 @@ export class OrcadSourceExportPersistence {
     ).payload
   }
 
+  /** This desktop's drafts for what `manifest` moves, keyed as the server names the worktrees. */
+  collectOrcadMigrationSourceDrafts(manifest: OrcadMigrationManifest): OrcadMigrationSourceDrafts {
+    return collectOrcadMigrationSourceDrafts(this[orcadSourceExportContext].state, manifest)
+  }
+
   /** A copy of the source with `moved` subtracted from it, for a delta move. */
   createOrcadMigrationDeltaView(moved: OrcadMigrationManifest): OrcadMigrationDeltaView {
     return createOrcadMigrationDeltaView(this[orcadSourceExportContext], moved)
diff --git a/src/main/persistence/migrating-orcad-catalog/orcad-source-release-upgrade.test.ts b/src/main/persistence/migrating-orcad-catalog/orcad-source-release-upgrade.test.ts
index 1b1d7a39b87..f8bbd78594d 100644
--- a/src/main/persistence/migrating-orcad-catalog/orcad-source-release-upgrade.test.ts
+++ b/src/main/persistence/migrating-orcad-catalog/orcad-source-release-upgrade.test.ts
@@ -10,6 +10,7 @@ import { createOrcadMigrationManifest } from '../../ssh/orcad-migration-manifest
 import { collectOrcadMigrationSourceDormantState } from './orcad-source-dormant-state'
 import { collectOrcadMigrationUntransferredDependencyCensus } from './orcad-source-dependency-census'
 import { subtractOrcadMigrationSourceDormantState } from './orcad-source-dormant-subtraction'
+import { collectOrcadMigrationSourceDrafts } from './orcad-source-draft-rename'
 
 const TARGET = {
   id: 'ssh-prod',
@@ -62,6 +63,16 @@ function draft(): PersistedOpenFile {
   }
 }
 
+/** The tab the server gets, while the draft stays here for the commit to rename. */
+function expectDraftKeptHere(state: PersistedState): void {
+  const manifest = exportState(state)
+  const { dirtyDraftContent: _draft, ...tab } = draft()
+  expect(manifest.payload.dormantState?.workspaceSession?.openFilesByWorktree?.[WORKTREE]).toEqual([
+    tab
+  ])
+  expect(collectOrcadMigrationSourceDrafts(state, manifest)[WORKTREE]).toEqual([draft()])
+}
+
 function sourceState(): PersistedState {
   const state = getDefaultPersistedState('/home/user')
   state.sshTargets = [TARGET]
@@ -248,7 +259,7 @@ describe('migrating saved state from released SSH clients', () => {
       expect(census(state).totalCount).toBe(0)
       const session = exportState(state).payload.dormantState?.workspaceSession
       expect(session?.tabsByWorktree[WORKTREE]?.map((tab) => tab.id)).toEqual(['local'])
-      expect(session?.openFilesByWorktree?.[WORKTREE]).toEqual([draft()])
+      expectDraftKeptHere(state)
       expect(session?.sleepingAgentSessionsByPaneKey ?? {}).toEqual({})
     })
 
@@ -287,7 +298,7 @@ describe('migrating saved state from released SSH clients', () => {
       expect(census(state).totalCount).toBe(0)
       const session = exportState(state).payload.dormantState?.workspaceSession
       expect(session?.tabsByWorktree[WORKTREE]?.map((tab) => tab.id)).toEqual(['host'])
-      expect(session?.openFilesByWorktree?.[WORKTREE]).toEqual([draft()])
+      expectDraftKeptHere(state)
     })
 
     it('refuses when the host holds a different copy of the file with the local draft', () => {
diff --git a/src/main/persistence/migrating-orcad-catalog/orcad-source-workspace-session.ts b/src/main/persistence/migrating-orcad-catalog/orcad-source-workspace-session.ts
index f07cb4bf549..648373d427c 100644
--- a/src/main/persistence/migrating-orcad-catalog/orcad-source-workspace-session.ts
+++ b/src/main/persistence/migrating-orcad-catalog/orcad-source-workspace-session.ts
@@ -35,6 +35,7 @@ import {
   resolveCopiesForHost,
   type SessionFragment
 } from './orcad-source-session-copy-resolution'
+import { withoutOrcadMigrationDrafts } from './orcad-source-draft-rename'
 import { hasClosedTerminalTabRecord } from '../../../shared/closed-terminal-tab-tombstones'
 import { LOCAL_EXECUTION_HOST_ID } from '../../../shared/execution-host'
 import { normalizeWorkspaceSessionKeyToWorkspaceId } from '../../../shared/workspace-scope'
@@ -240,8 +241,14 @@ function collectWorkspaceSession(
   if (duplicates.length > 0) {
     return { payload: undefined, snapshots: [], blockedItems: duplicates, leftBehindItems }
   }
+  // Drafts stay on this desktop; the commit renames them to the server (orcad-source-draft-rename).
   return merged.session
-    ? { payload: merged.session, snapshots, blockedItems: [], leftBehindItems }
+    ? {
+        payload: withoutOrcadMigrationDrafts(merged.session),
+        snapshots,
+        blockedItems: [],
+        leftBehindItems
+      }
     : {
         payload: undefined,
         snapshots: [],
diff --git a/src/main/ssh/orcad-migration-delta-move.test.ts b/src/main/ssh/orcad-migration-delta-move.test.ts
index 8c6f12e1934..85d9b221a28 100644
--- a/src/main/ssh/orcad-migration-delta-move.test.ts
+++ b/src/main/ssh/orcad-migration-delta-move.test.ts
@@ -600,12 +600,12 @@ async function connectAgain(): Promise<void> {
   await resolveHostServerOnConnect(target, {
     ...hostServerDepsStub(),
     managedEnvironmentId: () => environmentId,
-    retainCommittedSource: (host) => {
+    retainCommittedSource: async (host) => {
       const head = listOrcadMigrationSourceCutovers(userDataPath).find(
         (journal) => journal.sshTargetId === host.id && !journal.sourceRetainedAt
       )
       if (head?.phase === 'destination-committed') {
-        retainOrcadMigrationSource(userDataPath, head.migrationId, now)
+        await retainOrcadMigrationSource(userDataPath, head.migrationId, store, now)
       }
     }
   })
diff --git a/src/main/ssh/orcad-migration-delta-move.ts b/src/main/ssh/orcad-migration-delta-move.ts
index f83392a8c52..e949fd1fc71 100644
--- a/src/main/ssh/orcad-migration-delta-move.ts
+++ b/src/main/ssh/orcad-migration-delta-move.ts
@@ -177,7 +177,7 @@ async function commitDelta(
       throw error
     }
   }
-  retainOrcadMigrationSource(userDataPath, cutover.migrationId, now)
+  await retainOrcadMigrationSource(userDataPath, cutover.migrationId, store, now)
   return { outcome: 'moved', migrationId: cutover.migrationId }
 }
 
diff --git a/src/main/ssh/orcad-migration-source-retention.test.ts b/src/main/ssh/orcad-migration-source-retention.test.ts
index 3c31b2f722c..637c9dddf92 100644
--- a/src/main/ssh/orcad-migration-source-retention.test.ts
+++ b/src/main/ssh/orcad-migration-source-retention.test.ts
@@ -3,38 +3,104 @@ import { tmpdir } from 'node:os'
 import { join } from 'node:path'
 import { afterEach, beforeEach, describe, expect, it } from 'vitest'
 
+import type { Repo } from '../../shared/repo-types'
+import type { PersistedOpenFile } from '../../shared/workspace-session-state-types'
+import { closeTestStores, createSqliteTestStore } from '../persistence-test-harness'
+import { Store } from '../persistence/loading-store/store'
 import {
   listOrcadMigrationSourceCutovers,
   writeOrcadMigrationSourceCutover
 } from './orcad-migration-cutover-journal'
 import { orcadMigrationCutoverFixture } from './orcad-migration-cutover-fixture'
 import { listPendingManagedOrcadMigrations } from '../managed-server/lifecycle/orcad-managed-migration-status'
-import { retainOrcadMigrationSource } from './orcad-migration-source-retention'
+import {
+  retainUnretainedOrcadMigrationSources,
+  retainOrcadMigrationSource
+} from './orcad-migration-source-retention'
+
+const TARGET_ID = 'ssh-1'
+const SOURCE_HOST = `ssh:${TARGET_ID}`
+const SERVER_HOST = 'runtime:env-1'
+const WORKTREE = 'repo-1::/srv/app'
+const REPO: Repo = {
+  id: 'repo-1',
+  path: '/srv/app',
+  displayName: 'app',
+  badgeColor: '#737373',
+  addedAt: 1,
+  kind: 'git',
+  connectionId: TARGET_ID
+}
 
 let userDataPath: string
+let store: Store
 
 beforeEach(() => {
   userDataPath = mkdtempSync(join(tmpdir(), 'orcad-retention-'))
+  store = createSqliteTestStore(Store, { dataFile: join(userDataPath, 'orca-data.json') })
 })
 
-afterEach(() => {
+afterEach(async () => {
+  await closeTestStores()
   rmSync(userDataPath, { recursive: true, force: true })
 })
 
+function committed(migrationId = 'm-1') {
+  const cutover = orcadMigrationCutoverFixture(migrationId, TARGET_ID)
+  return {
+    ...cutover,
+    phase: 'destination-committed' as const,
+    manifest: {
+      ...cutover.manifest,
+      payload: { ...cutover.manifest.payload, repositories: [REPO] }
+    }
+  }
+}
+
+function draftedFile(filePath: string, draft: string): PersistedOpenFile {
+  return {
+    filePath,
+    relativePath: filePath.slice('/srv/app/'.length),
+    worktreeId: WORKTREE,
+    language: 'markdown',
+    dirtyDraftContent: draft,
+    lastKnownDiskSignature: 'base-1'
+  }
+}
+
+function saveFiles(hostId: string, files: PersistedOpenFile[]): void {
+  store.setWorkspaceSession(
+    { ...store.getWorkspaceSession(hostId), openFilesByWorktree: { [WORKTREE]: files } },
+    hostId
+  )
+}
+
+async function restart(): Promise<void> {
+  await store.flushPendingOrThrowAsync()
+  await closeTestStores()
+  store = createSqliteTestStore(Store, { dataFile: join(userDataPath, 'orca-data.json') })
+}
+
+const serverFiles = () => store.getWorkspaceSession(SERVER_HOST).openFilesByWorktree?.[WORKTREE]
+
 describe('retaining a committed migration source', () => {
-  it('marks only a committed cutover, idempotently, and stops counting it as pending', () => {
+  it('marks only a committed cutover, idempotently, and stops counting it as pending', async () => {
     writeOrcadMigrationSourceCutover(userDataPath, orcadMigrationCutoverFixture('m-1'))
-    expect(() => retainOrcadMigrationSource(userDataPath, 'm-1')).toThrow(
+    await expect(retainOrcadMigrationSource(userDataPath, 'm-1', store)).rejects.toThrow(
       'orcad_migration_retain_before_commit'
     )
-    const committed = {
+    writeOrcadMigrationSourceCutover(userDataPath, {
       ...orcadMigrationCutoverFixture('m-1'),
-      phase: 'destination-committed' as const
-    }
-    writeOrcadMigrationSourceCutover(userDataPath, committed)
+      phase: 'destination-committed'
+    })
     const at = () => new Date('2026-10-03T00:00:00.000Z')
-    retainOrcadMigrationSource(userDataPath, 'm-1', at)
-    retainOrcadMigrationSource(userDataPath, 'm-1', () => new Date('2026-12-01T00:00:00.000Z'))
+    await retainOrcadMigrationSource(userDataPath, 'm-1', store, at)
+    await retainOrcadMigrationSource(
+      userDataPath,
+      'm-1',
+      store,
+      () => new Date('2026-12-01T00:00:00.000Z')
+    )
     expect(listOrcadMigrationSourceCutovers(userDataPath)[0]?.sourceRetainedAt).toBe(
       '2026-10-03T00:00:00.000Z'
     )
@@ -55,3 +121,142 @@ describe('retaining a committed migration source', () => {
     ).not.toThrow()
   })
 })
+
+describe('renaming unsaved drafts to the server on commit', () => {
+  beforeEach(() => {
+    store.addSshTarget({
+      id: TARGET_ID,
+      label: 'Prod',
+      host: 'h',
+      port: 22,
+      username: 'u',
+      generation: 2
+    })
+    store.addRepo(REPO)
+  })
+
+  it('moves the host and desktop drafts, with their baseline, and leaves the source as it was', async () => {
+    saveFiles(SOURCE_HOST, [draftedFile('/srv/app/host.md', 'host draft')])
+    saveFiles('local', [draftedFile('/srv/app/desktop.md', 'desktop draft')])
+    const source = JSON.stringify(store.getWorkspaceSession(SOURCE_HOST))
+    writeOrcadMigrationSourceCutover(userDataPath, committed())
+
+    await retainOrcadMigrationSource(userDataPath, 'm-1', store)
+
+    expect(serverFiles()).toEqual([
+      { ...draftedFile('/srv/app/host.md', 'host draft'), runtimeEnvironmentId: 'env-1' },
+      { ...draftedFile('/srv/app/desktop.md', 'desktop draft'), runtimeEnvironmentId: 'env-1' }
+    ])
+    expect(listOrcadMigrationSourceCutovers(userDataPath)[0]?.sourceRetainedAt).toBeDefined()
+    expect(JSON.stringify(store.getWorkspaceSession(SOURCE_HOST))).toBe(source)
+    await store.flushPendingOrThrowAsync()
+    await closeTestStores()
+    store = createSqliteTestStore(Store, { dataFile: join(userDataPath, 'orca-data.json') })
+    expect(serverFiles()?.map((file) => file.dirtyDraftContent)).toEqual([
+      'host draft',
+      'desktop draft'
+    ])
+  })
+
+  it('keeps what the server partition already holds, and never revives a discarded draft', async () => {
+    saveFiles(SOURCE_HOST, [
+      draftedFile('/srv/app/a.md', 'source A'),
+      draftedFile('/srv/app/b.md', 'source B')
+    ])
+    saveFiles(SERVER_HOST, [{ ...draftedFile('/srv/app/a.md', 'newer A') }])
+    writeOrcadMigrationSourceCutover(userDataPath, committed())
+
+    await retainOrcadMigrationSource(userDataPath, 'm-1', store)
+    expect(serverFiles()?.map((file) => file.dirtyDraftContent)).toEqual(['newer A', 'source B'])
+
+    saveFiles(SERVER_HOST, [])
+    await retainOrcadMigrationSource(userDataPath, 'm-1', store)
+    expect(serverFiles()).toEqual([])
+    await restart()
+    await retainUnretainedOrcadMigrationSources(userDataPath, store)
+    await retainOrcadMigrationSource(userDataPath, 'm-1', store)
+    expect(serverFiles()).toEqual([])
+  })
+
+  it('renames and retains at startup after a cut-off commit, so a draft closed later stays closed', async () => {
+    saveFiles(SOURCE_HOST, [draftedFile('/srv/app/a.md', 'source A')])
+    writeOrcadMigrationSourceCutover(userDataPath, committed())
+    await restart()
+
+    await retainUnretainedOrcadMigrationSources(userDataPath, store)
+    expect(serverFiles()?.map((file) => file.dirtyDraftContent)).toEqual(['source A'])
+    expect(listOrcadMigrationSourceCutovers(userDataPath)[0]?.sourceRetainedAt).toBeDefined()
+    // Closed before any connect: neither the connect's retain nor a later start brings it back.
+    saveFiles(SERVER_HOST, [])
+    await retainOrcadMigrationSource(userDataPath, 'm-1', store)
+    await retainUnretainedOrcadMigrationSources(userDataPath, store)
+    await restart()
+    await retainUnretainedOrcadMigrationSources(userDataPath, store)
+    expect(serverFiles()).toEqual([])
+  })
+
+  it('shares one retain between concurrent callers, so a later one never renames again', async () => {
+    saveFiles(SOURCE_HOST, [draftedFile('/srv/app/a.md', 'source A')])
+    writeOrcadMigrationSourceCutover(userDataPath, committed())
+    const first = retainOrcadMigrationSource(userDataPath, 'm-1', store)
+    expect(retainOrcadMigrationSource(userDataPath, 'm-1', store)).toBe(first)
+    await first
+    saveFiles(SERVER_HOST, [])
+    await retainOrcadMigrationSource(userDataPath, 'm-1', store)
+    expect(serverFiles()).toEqual([])
+  })
+
+  it("never retains another profile's migration at startup", async () => {
+    writeOrcadMigrationSourceCutover(userDataPath, {
+      ...orcadMigrationCutoverFixture('m-9', 'ssh-other-profile'),
+      phase: 'destination-committed'
+    })
+    await retainUnretainedOrcadMigrationSources(userDataPath, store)
+    expect(listOrcadMigrationSourceCutovers(userDataPath)[0]?.sourceRetainedAt).toBeUndefined()
+  })
+
+  it('keeps newer typing in the server copy when the connect retains first', async () => {
+    saveFiles(SOURCE_HOST, [draftedFile('/srv/app/a.md', 'source A')])
+    saveFiles(SERVER_HOST, [
+      { ...draftedFile('/srv/app/a.md', 'typed after'), runtimeEnvironmentId: 'env-1' }
+    ])
+    writeOrcadMigrationSourceCutover(userDataPath, committed())
+    await retainOrcadMigrationSource(userDataPath, 'm-1', store)
+    await retainUnretainedOrcadMigrationSources(userDataPath, store)
+    expect(serverFiles()?.map((file) => file.dirtyDraftContent)).toEqual(['typed after'])
+  })
+
+  it('makes the startup rename durable before its retained mark', async () => {
+    saveFiles(SOURCE_HOST, [draftedFile('/srv/app/a.md', 'source A')])
+    writeOrcadMigrationSourceCutover(userDataPath, committed())
+    await restart()
+    await retainUnretainedOrcadMigrationSources(userDataPath, store)
+    expect(listOrcadMigrationSourceCutovers(userDataPath)[0]?.sourceRetainedAt).toBeDefined()
+    // A crash now: a second reader sees only what reached disk.
+    const crashed = createSqliteTestStore(Store, { dataFile: join(userDataPath, 'orca-data.json') })
+    expect(
+      crashed.getWorkspaceSession(SERVER_HOST).openFilesByWorktree?.[WORKTREE]?.[0]
+        ?.dirtyDraftContent
+    ).toBe('source A')
+  })
+
+  it("leaves another host's file and another project's draft where they are", async () => {
+    saveFiles(SOURCE_HOST, [
+      { ...draftedFile('/srv/app/remote.md', 'other host'), runtimeEnvironmentId: 'env-9' }
+    ])
+    store.setWorkspaceSession(
+      {
+        ...store.getWorkspaceSession(SOURCE_HOST),
+        openFilesByWorktree: {
+          ...store.getWorkspaceSession(SOURCE_HOST).openFilesByWorktree,
+          'repo-2::/srv/other': [draftedFile('/srv/other/x.md', 'other project')]
+        }
+      },
+      SOURCE_HOST
+    )
+    writeOrcadMigrationSourceCutover(userDataPath, committed())
+
+    await retainOrcadMigrationSource(userDataPath, 'm-1', store)
+    expect(store.getWorkspaceSession(SERVER_HOST).openFilesByWorktree ?? {}).toEqual({})
+  })
+})
diff --git a/src/main/ssh/orcad-migration-source-retention.ts b/src/main/ssh/orcad-migration-source-retention.ts
index b95196a7547..a05153dcfa1 100644
--- a/src/main/ssh/orcad-migration-source-retention.ts
+++ b/src/main/ssh/orcad-migration-source-retention.ts
@@ -3,30 +3,153 @@
  * its projects and can reach them over its own relay. New builds hide those rows and serve the host
  * from the server. They are never deleted automatically.
  */
+import { toRuntimeExecutionHostId } from '../../shared/execution-host'
 import type { OrcadMigrationSourceCutover } from '../../shared/orcad-migration/orcad-migration-source-cutover'
+import type { WorkspaceSessionState } from '../../shared/workspace-session-state-types'
+import type { Store } from '../persistence'
+import { withRenamedOrcadMigrationDrafts } from '../persistence/migrating-orcad-catalog/orcad-source-draft-rename'
 import {
   listOrcadMigrationSourceCutovers,
   writeOrcadMigrationSourceCutover
 } from './orcad-migration-cutover-journal'
 
-/** Marks a committed migration as finished for this build while its source rows stay. */
+export type OrcadMigrationDraftRenameStore = Pick<
+  Store,
+  | 'collectOrcadMigrationSourceDrafts'
+  | 'getWorkspaceSession'
+  | 'runDurableMutation'
+  | 'setWorkspaceSession'
+>
+
+// One retain per migration at a time: a second caller waits for the first and then finds it done.
+const retainsInFlight = new Map<string, Promise<OrcadMigrationSourceCutover>>()
+
+/**
+ * Marks a committed migration as finished for this build while its source rows stay. Its unsaved
+ * drafts are renamed to the server first, durably, so the retained mark proves they were.
+ */
 export function retainOrcadMigrationSource(
   userDataPath: string,
   migrationId: string,
+  store: OrcadMigrationDraftRenameStore,
   now: () => Date = () => new Date()
-): OrcadMigrationSourceCutover {
+): Promise<OrcadMigrationSourceCutover> {
+  const pending = retainsInFlight.get(migrationId)
+  if (pending) {
+    return pending
+  }
+  const retain = retainOnce(userDataPath, migrationId, store, now).finally(() =>
+    retainsInFlight.delete(migrationId)
+  )
+  retainsInFlight.set(migrationId, retain)
+  return retain
+}
+
+async function retainOnce(
+  userDataPath: string,
+  migrationId: string,
+  store: OrcadMigrationDraftRenameStore,
+  now: () => Date
+): Promise<OrcadMigrationSourceCutover> {
+  const cutover = readCommittedCutover(userDataPath, migrationId)
+  if (cutover.sourceRetainedAt) {
+    return cutover
+  }
+  await store.runDurableMutation(() => {
+    const renamed = renamedDestinationSession(store, cutover)
+    if (!renamed) {
+      // A startup rename may still be only in memory; the retained mark must not outrun it.
+      return { value: undefined, persist: 'if-dirty' }
+    }
+    // No rollback: the renamed rows are correct either way, and a retry adds nothing twice.
+    writeDestinationSession(store, cutover, renamed.next)
+    return { value: undefined }
+  })
+  // Why no baseline here: the source may have changed since the commit (a crash, then an older
+  // build); only the fence's pre-commit baseline proves what the server holds.
+  const retained = {
+    ...readCommittedCutover(userDataPath, migrationId),
+    sourceRetainedAt: now().toISOString()
+  }
+  writeOrcadMigrationSourceCutover(userDataPath, retained)
+  return retained
+}
+
+/**
+ * At startup, for a commit whose retained mark a crash cut off: its drafts are renamed before any
+ * window reads its sessions, since a renderer that booted without them would overwrite them; then
+ * the move is retained, so the rename never runs again and a draft closed later stays closed.
+ */
+export function retainUnretainedOrcadMigrationSources(
+  userDataPath: string,
+  store: OrcadMigrationDraftRenameStore & Pick<Store, 'getSshTarget'>
+): Promise<void> {
+  const migrationIds: string[] = []
+  try {
+    for (const cutover of listOrcadMigrationSourceCutovers(userDataPath)) {
+      // Journals are shared across profiles; only the profile that owns the host can rename.
+      const target = store.getSshTarget(cutover.sshTargetId)
+      if (
+        cutover.phase !== 'destination-committed' ||
+        cutover.sourceRetainedAt ||
+        target?.generation !== cutover.sshTargetGeneration
+      ) {
+        continue
+      }
+      const renamed = renamedDestinationSession(store, cutover)
+      if (renamed) {
+        writeDestinationSession(store, cutover, renamed.next)
+      }
+      migrationIds.push(cutover.migrationId)
+    }
+  } catch (error) {
+    // The connect's retain renames them instead; startup must not fail on an unreadable journal.
+    console.warn('[ssh] Could not rename committed migrations’ unsaved drafts:', error)
+  }
+  return Promise.all(
+    migrationIds.map((migrationId) =>
+      retainOrcadMigrationSource(userDataPath, migrationId, store).catch((error: unknown) => {
+        console.warn('[ssh] Could not mark a finished migration retained:', error)
+      })
+    )
+  ).then(() => undefined)
+}
+
+function readCommittedCutover(userDataPath: string, migrationId: string) {
   const cutover = listOrcadMigrationSourceCutovers(userDataPath).find(
     (entry) => entry.migrationId === migrationId
   )
   if (!cutover || cutover.phase !== 'destination-committed') {
     throw new Error('orcad_migration_retain_before_commit')
   }
-  if (cutover.sourceRetainedAt) {
-    return cutover
-  }
-  // Why no baseline here: the source may have changed since the commit (a crash, then an older
-  // build); only the fence's pre-commit baseline proves what the server holds.
-  const retained = { ...cutover, sourceRetainedAt: now().toISOString() }
-  writeOrcadMigrationSourceCutover(userDataPath, retained)
-  return retained
+  return cutover
+}
+
+/** Only files the server partition lacks, so the retain after a startup rename adds nothing. */
+function renamedDestinationSession(
+  store: Pick<
+    OrcadMigrationDraftRenameStore,
+    'collectOrcadMigrationSourceDrafts' | 'getWorkspaceSession'
+  >,
+  cutover: OrcadMigrationSourceCutover
+): { next: WorkspaceSessionState } | null {
+  const before = store.getWorkspaceSession(
+    toRuntimeExecutionHostId(cutover.destinationEnvironmentId)
+  )
+  const next = withRenamedOrcadMigrationDrafts(
+    before,
+    store.collectOrcadMigrationSourceDrafts(cutover.manifest),
+    cutover.destinationEnvironmentId
+  )
+  return next ? { next } : null
+}
+
+function writeDestinationSession(
+  store: Pick<OrcadMigrationDraftRenameStore, 'setWorkspaceSession'>,
+  cutover: OrcadMigrationSourceCutover,
+  session: WorkspaceSessionState
+): void {
+  // Baselined writer: drafts are desktop view state no layout command carries (LayoutEditorFile
+  // omits them), and the tabs themselves reach the server only through the manifest.
+  store.setWorkspaceSession(session, toRuntimeExecutionHostId(cutover.destinationEnvironmentId))
 }
diff --git a/src/main/ssh/orcad-migration-source.ts b/src/main/ssh/orcad-migration-source.ts
index fb214235095..e1f9a7112b6 100644
--- a/src/main/ssh/orcad-migration-source.ts
+++ b/src/main/ssh/orcad-migration-source.ts
@@ -24,8 +24,6 @@ export type OrcadMigrationSourceCutoverPort = {
   verifyFence: (cutover: OrcadMigrationSourceCutover) => void
   /** Drops the fence, then the journal; only on proof the destination holds nothing. */
   releaseFence: (cutover: OrcadMigrationSourceCutover) => Promise<void>
-  /** After a proven commit: the source rows stay, hidden, for a downgraded build. */
-  retireAfterCommit: (migrationId: string, now?: () => Date) => OrcadMigrationSourceCutover
 }
 
 export type OrcadMigrationFenceAcquireArgs = {
diff --git a/src/main/ssh/orcad-migration-ssh-relay-source.ts b/src/main/ssh/orcad-migration-ssh-relay-source.ts
index 22051ad8195..7de480b3f69 100644
--- a/src/main/ssh/orcad-migration-ssh-relay-source.ts
+++ b/src/main/ssh/orcad-migration-ssh-relay-source.ts
@@ -15,7 +15,6 @@ import {
   releaseOrcadMigrationFence,
   resolveOrcadMigrationFence
 } from './orcad-migration-source-fence'
-import { retainOrcadMigrationSource } from './orcad-migration-source-retention'
 import {
   assessOrcadMigrationTerminals,
   retireProvenExitedLeases,
@@ -43,9 +42,7 @@ export function sshRelayMigrationCutoverPort(
         { userDataPath: deps.userDataPath, store: deps.freshSource?.() ?? deps.store },
         cutover
       ),
-    releaseFence: (cutover) => releaseOrcadMigrationFence(deps, cutover),
-    retireAfterCommit: (migrationId, now) =>
-      retainOrcadMigrationSource(deps.userDataPath, migrationId, now)
+    releaseFence: (cutover) => releaseOrcadMigrationFence(deps, cutover)
   }
 }
 
diff --git a/src/main/ssh/orcad-migration-stuck-host-profiles.test.ts b/src/main/ssh/orcad-migration-stuck-host-profiles.test.ts
index 2e2764f5483..f1ccbcf047e 100644
--- a/src/main/ssh/orcad-migration-stuck-host-profiles.test.ts
+++ b/src/main/ssh/orcad-migration-stuck-host-profiles.test.ts
@@ -395,7 +395,55 @@ describe('"Move anyway"', () => {
     })
   })
 
-  it("carries the desktop copy's drafts when the host's copy of the tabs wins", async () => {
+  it("moves past an unsaved draft of the host's own file that only this desktop holds", async () => {
+    const state = savedStateOnly()
+    state.workspaceSession.openFilesByWorktree = {
+      [worktreeId]: [
+        {
+          filePath: '/home/dev/src/project-0/notes.md',
+          relativePath: 'notes.md',
+          worktreeId,
+          language: 'markdown',
+          dirtyDraftContent: 'desktop draft'
+        }
+      ]
+    }
+    delete state.workspaceSession.tabsByWorktree[worktreeId]
+    const loaded = load(state)
+    confirmed(loaded)
+    const result = await connectMove(loaded)
+    expect(result).toMatchObject({ outcome: 'fenced' })
+    if ('cutover' in result) {
+      expect(
+        loaded.store.collectOrcadMigrationSourceDrafts(result.cutover.manifest)[worktreeId]
+      ).toEqual([expect.objectContaining({ dirtyDraftContent: 'desktop draft' })])
+    }
+  })
+
+  it('still refuses two different unsaved versions of one file, since only one can be renamed', async () => {
+    const state = savedStateOnly()
+    const notes = (dirtyDraftContent: string) => ({
+      filePath: '/home/dev/src/project-0/notes.md',
+      relativePath: 'notes.md',
+      worktreeId,
+      language: 'markdown',
+      dirtyDraftContent
+    })
+    state.workspaceSessionsByHostId![HOST]!.openFilesByWorktree![worktreeId]!.push(notes('host'))
+    state.workspaceSession.openFilesByWorktree = { [worktreeId]: [notes('desktop')] }
+    // An unrelated project's draft must not let the clash slip past as a left-behind item.
+    state.workspaceSessionsByHostId![HOST]!.openFilesByWorktree!['repo-9::/srv/other'] = [
+      { ...notes('other project'), worktreeId: 'repo-9::/srv/other', filePath: '/srv/other/x.md' }
+    ]
+    const loaded = load(state)
+    confirmed(loaded)
+    await expect(connectMove(loaded)).resolves.toMatchObject({
+      outcome: 'refused',
+      reason: expect.stringContaining('unsaved changes to /home/dev/src/project-0/notes.md')
+    })
+  })
+
+  it("keeps the desktop copy's drafts here when the host's copy of the tabs wins", async () => {
     const state = savedStateOnly()
     state.workspaceSession.openFilesByWorktree = {
       [worktreeId]: [
@@ -417,9 +465,13 @@ describe('"Move anyway"', () => {
     }
     const session = result.cutover.manifest.payload.dormantState?.workspaceSession
     expect(session?.tabsByWorktree[worktreeId]?.map((tab) => tab.id)).toEqual(['tab-1'])
+    // The server gets the tab; the commit renames the draft into this desktop's server partition.
     expect(session?.openFilesByWorktree?.[worktreeId]).toEqual([
-      expect.objectContaining({ dirtyDraftContent: 'desktop draft' })
+      expect.not.objectContaining({ dirtyDraftContent: expect.anything() })
     ])
+    expect(
+      loaded.store.collectOrcadMigrationSourceDrafts(result.cutover.manifest)[worktreeId]
+    ).toEqual([expect.objectContaining({ dirtyDraftContent: 'desktop draft' })])
   })
 
   it('moves a pane whose saved history is gone, without that history', async () => {
diff --git a/src/main/ssh/ssh-host-server-on-connect-test-deps.ts b/src/main/ssh/ssh-host-server-on-connect-test-deps.ts
index c67d5b737b2..c90776fa773 100644
--- a/src/main/ssh/ssh-host-server-on-connect-test-deps.ts
+++ b/src/main/ssh/ssh-host-server-on-connect-test-deps.ts
@@ -12,7 +12,7 @@ export function hostServerDepsStub(
     managedEnvironmentId: () => null,
     ensureTunnel: vi.fn(async () => undefined),
     ensureServing: vi.fn(async () => ({ state: 'serving' as const })),
-    retainCommittedSource: vi.fn(),
+    retainCommittedSource: vi.fn(async () => {}),
     hasUnfinishedConversion: () => false,
     abandonConversion: vi.fn(async () => undefined),
     abandonDeploy: vi.fn(async () => undefined),
diff --git a/src/main/ssh/ssh-host-server-on-connect.ts b/src/main/ssh/ssh-host-server-on-connect.ts
index 268cbb394e4..a52c957ad46 100644
--- a/src/main/ssh/ssh-host-server-on-connect.ts
+++ b/src/main/ssh/ssh-host-server-on-connect.ts
@@ -88,7 +88,7 @@ export type HostServerOnConnectDeps = {
   /** Behind the tunnel: answers, or is started from its activated slot if proven stopped. */
   ensureServing: (environmentId: string) => Promise<OrcadManagedServing>
   /** Marks a commit whose reply outlived the move as finished; its source rows are kept. */
-  retainCommittedSource: (target: SshTarget) => void
+  retainCommittedSource: (target: SshTarget) => Promise<void>
   /** False when this build carries no orcad template, so nothing is tried on the host. */
   hasTemplate: () => boolean
   /** A recorded "orcad can't run here" whose key still matches this build. */
@@ -172,7 +172,7 @@ async function decide(
       return unserved
     }
     try {
-      deps.retainCommittedSource(target)
+      await deps.retainCommittedSource(target)
     } catch (error) {
       console.warn('[ssh] Could not mark a finished migration retained:', error)
     }
diff --git a/tests/e2e/helpers/orcad-convert-host.ts b/tests/e2e/helpers/orcad-convert-host.ts
index 800043b4108..82285c0cc6e 100644
--- a/tests/e2e/helpers/orcad-convert-host.ts
+++ b/tests/e2e/helpers/orcad-convert-host.ts
@@ -29,6 +29,8 @@ export type OrcadConvertHost = {
   blockTcpForwarding?: () => void
   /** Docker only: runs a shell command on the host as the SSH user and returns its stdout. */
   exec?: (command: string) => string
+  /** Docker only: copies a host path (file or directory) to a local path. */
+  copyFromHost?: (remotePath: string, localPath: string) => void
   /** Docker only: kills every live SSH connection, leaving sshd listening; returns how many. */
   dropSshConnections?: () => number
   /** Docker only: freezes or thaws the whole host; TCP stays up but nothing answers. */
@@ -66,6 +68,11 @@ export function startOrcadConvertHost(source: string, testInfo: TestInfo): Orcad
       cleanup: () => cleanupDockerSshHostTarget(target),
       blockTcpForwarding: () => blockDockerSshHostTargetTcpForwarding(target),
       exec: (command) => execDockerSshHostTargetCommand(target, command),
+      copyFromHost: (remotePath, localPath) =>
+        execFileSync('docker', ['cp', `${target.containerName}:${remotePath}`, localPath], {
+          stdio: 'ignore',
+          timeout: 60_000
+        }),
       dropSshConnections: () =>
         Number(
           execDockerSshHostTargetControlCommand(target, DROP_SSH_CONNECTIONS).split('\n').at(-1)
diff --git a/tests/e2e/helpers/orcad-managed-workspace.ts b/tests/e2e/helpers/orcad-managed-workspace.ts
index 9c102a1957b..e1f111e3e7a 100644
--- a/tests/e2e/helpers/orcad-managed-workspace.ts
+++ b/tests/e2e/helpers/orcad-managed-workspace.ts
@@ -63,6 +63,8 @@ export type ManagedProfileOptions = {
   repoPath?: string
   /** Overrides the host's folder workspace, e.g. to keep /tmp outside every workspace. */
   folderPath?: string
+  /** Passed through to the relay-era seed, e.g. an unsaved editor draft. */
+  seed?: Pick<NonNullable<Parameters<typeof seedRelayEraProfile>[3]>, 'draftContent'>
   /** Runs on the profile-creating launch, before the SSH profile is seeded. */
   beforeSeed?: (page: Page) => Promise<void>
   /** Runs as soon as the converting launch starts, before the session is ready. */
@@ -82,10 +84,15 @@ export async function launchConvertedProfile(
   await options.beforeSeed?.(first.page)
   await session.close(first.app)
   fixture.app = null
-  const seeded = seedRelayEraProfile(session.userDataDir, host.input, {
-    repoPath: options.repoPath ?? host.remoteRepoPath,
-    folderPath: options.folderPath ?? host.remoteFolderPath
-  })
+  const seeded = seedRelayEraProfile(
+    session.userDataDir,
+    host.input,
+    {
+      repoPath: options.repoPath ?? host.remoteRepoPath,
+      folderPath: options.folderPath ?? host.remoteFolderPath
+    },
+    options.seed
+  )
   const { app, page } = await session.launch()
   fixture.app = app
   await options.onLaunch?.(page, seeded)
diff --git a/tests/e2e/helpers/orcad-upgrade-profile.ts b/tests/e2e/helpers/orcad-upgrade-profile.ts
index 7b18ad716a4..28f9a25bebd 100644
--- a/tests/e2e/helpers/orcad-upgrade-profile.ts
+++ b/tests/e2e/helpers/orcad-upgrade-profile.ts
@@ -92,6 +92,8 @@ export function seedRelayEraProfile(
     targetId?: string
     /** COMPAT(legacy-relay-bridge): the terminal tab still runs this PTY in the host's relay. */
     relayPtyId?: string
+    /** An unsaved buffer on the editor tab, as hot exit persists it. */
+    draftContent?: string
   } = {}
 ): RelayEraProfile {
   const now = Date.now()
@@ -162,7 +164,8 @@ export function seedRelayEraProfile(
           relativePath: 'README.md',
           worktreeId,
           language: 'markdown',
-          runtimeEnvironmentId: null
+          runtimeEnvironmentId: null,
+          ...(options.draftContent === undefined ? {} : { dirtyDraftContent: options.draftContent })
         }
       ]
     },
diff --git a/tests/e2e/ssh-orcad-editor-drafts-migration.spec.ts b/tests/e2e/ssh-orcad-editor-drafts-migration.spec.ts
new file mode 100644
index 00000000000..fef785df5af
--- /dev/null
+++ b/tests/e2e/ssh-orcad-editor-drafts-migration.spec.ts
@@ -0,0 +1,216 @@
+/**
+ * S10 live check: an unsaved editor draft on a relay-era SSH host, converted to a managed server.
+ * Drafts stay on the desktop: after the converting connect and a reconnect the editor still holds
+ * the exact bytes, and the host server's stored profile holds none of them.
+ */
+import { createHash } from 'node:crypto'
+import { mkdirSync, mkdtempSync, readdirSync, rmSync } from 'node:fs'
+import { tmpdir } from 'node:os'
+import path from 'node:path'
+import type { Page, TestInfo } from '@stablyai/playwright-test'
+import { expect, test } from './helpers/orca-app'
+import {
+  activateManagedWorkspace,
+  launchManagedWorkspace,
+  managedEnvironmentId,
+  relaunchManagedApp,
+  skipUnlessManagedDockerHost,
+  withManagedHost,
+  type ManagedHostFixture
+} from './helpers/orcad-managed-workspace'
+import { reconnect } from './helpers/orcad-convert-flow'
+import { readPersistedProfileState } from './helpers/persisted-profile-state'
+
+skipUnlessManagedDockerHost()
+
+// A large markdown file opens in the source editor instead of the rich one.
+const VISIBLE_EDITOR = '.rich-markdown-editor, .monaco-editor .view-lines'
+
+type EditorVerdict = 'present' | 'dirty-only' | 'absent'
+type HostVerdict = { verdict: 'present' | 'mismatch' | 'absent'; where: string[] }
+
+function draftOf(marker: string, bytes: number): string {
+  const lines: string[] = []
+  let length = 0
+  for (let line = 0; length < bytes; line += 1) {
+    const text = `${marker} unsaved line ${line}\n`
+    lines.push(text)
+    length += text.length
+  }
+  return lines.join('').slice(0, bytes)
+}
+
+function sha256(text: string): string {
+  return createHash('sha256').update(text, 'utf8').digest('hex')
+}
+
+/** Every string in `value` equal to, or carrying, the draft, by JSON path. */
+function findDraft(value: unknown, draft: string, marker: string): HostVerdict {
+  const exact: string[] = []
+  const partial: string[] = []
+  const walk = (node: unknown, at: string): void => {
+    if (typeof node === 'string') {
+      if (node === draft) {
+        exact.push(at)
+      } else if (node.includes(marker)) {
+        partial.push(`${at} (${node.length} chars)`)
+      }
+      return
+    }
+    if (Array.isArray(node)) {
+      node.forEach((child, index) => walk(child, `${at}[${index}]`))
+      return
+    }
+    if (node && typeof node === 'object') {
+      for (const [key, child] of Object.entries(node)) {
+        walk(child, at ? `${at}.${key}` : key)
+      }
+    }
+  }
+  walk(value, '')
+  if (exact.length > 0) {
+    return { verdict: 'present', where: exact }
+  }
+  return partial.length > 0
+    ? { verdict: 'mismatch', where: partial }
+    : { verdict: 'absent', where: [] }
+}
+
+/** The managed server's committed profile, copied off the host so it is read as stored. */
+function readHostProfiles(fixture: ManagedHostFixture): Record<string, unknown>[] {
+  const { host } = fixture
+  const databases = host.exec!(
+    `find / -xdev -name profile-state.db -path '*/profiles/*' 2>/dev/null || true`
+  )
+    .split('\n')
+    .map((line) => line.trim())
+    .filter(Boolean)
+  const states: Record<string, unknown>[] = []
+  for (const database of databases) {
+    const profileDir = path.posix.dirname(database)
+    const profileId = path.posix.basename(profileDir)
+    const local = mkdtempSync(path.join(tmpdir(), 'orca-s10d-host-'))
+    try {
+      const profilesDir = path.join(local, 'profiles')
+      mkdirSync(profilesDir, { recursive: true })
+      // The directory carries the WAL beside the database: committed rows may still sit there.
+      host.copyFromHost!(profileDir, profilesDir)
+      if (readdirSync(path.join(profilesDir, profileId)).includes('profile-state.db')) {
+        states.push(readPersistedProfileState(local, profileId))
+      }
+    } finally {
+      rmSync(local, { recursive: true, force: true })
+    }
+  }
+  return states
+}
+
+async function readEditorVerdict(
+  page: Page,
+  filePath: string,
+  draft: string
+): Promise<{ verdict: EditorVerdict; detail: string }> {
+  const seen = await page.evaluate(
+    ({ filePath }) => {
+      const state = window.__store?.getState()
+      const files = (state?.openFiles ?? []).filter((file) => file.filePath === filePath)
+      return files.map((file) => ({
+        id: file.id,
+        worktreeId: file.worktreeId,
+        isDirty: file.isDirty,
+        draft: state?.editorDrafts[file.id] ?? null
+      }))
+    },
+    { filePath }
+  )
+  const detail = JSON.stringify(
+    seen.map(({ draft: content, ...rest }) => ({
+      ...rest,
+      draftChars: content?.length ?? null,
+      draftSha: content === null ? null : sha256(content)
+    }))
+  )
+  if (seen.some((file) => file.draft === draft)) {
+    return { verdict: 'present', detail }
+  }
+  return { verdict: seen.some((file) => file.isDirty) ? 'dirty-only' : 'absent', detail }
+}
+
+function record(testInfo: TestInfo, label: string, line: string): void {
+  console.log(`S10D-LIVE ${label} ${line}`)
+  testInfo.annotations.push({ type: 'S10D-LIVE', description: `${label} ${line}` })
+}
+
+for (const { label, bytes } of [
+  // Well inside the 768 KiB signed manifest.
+  { label: 'inline', bytes: 2 * 1024 },
+  // Over the 768 KiB manifest budget, which an inline draft used to overflow.
+  { label: 'large', bytes: 2 * 1024 * 1024 }
+]) {
+  test(`an unsaved ${label} editor draft survives conversion to a managed server`, async (// oxlint-disable-next-line no-empty-pattern -- This exercise owns its app launch.
+  {}, testInfo) => {
+    test.setTimeout(14 * 60_000)
+    await withManagedHost(testInfo, async (fixture) => {
+      const marker = `S10D_${label.toUpperCase()}_${Date.now()}`
+      const draft = draftOf(marker, bytes)
+      const { page, seeded } = await launchManagedWorkspace(fixture, {
+        seed: { draftContent: draft }
+      })
+      // A further reconnect: what the editor sees once the converted host is reached again.
+      await reconnect(page, seeded.targetId)
+      // The editor may hydrate the moved tab a moment after the reconnect settles.
+      let editor = await readEditorVerdict(page, seeded.sessionFilePath, draft)
+      await expect
+        .poll(
+          async () => {
+            editor = await readEditorVerdict(page, seeded.sessionFilePath, draft)
+            return editor.verdict
+          },
+          { timeout: 30_000 }
+        )
+        .toBe('present')
+        .catch(() => {})
+      await expect(page.locator(VISIBLE_EDITOR).first()).toContainText(`${marker} unsaved line 0`, {
+        timeout: 60_000
+      })
+      // A restart reads the draft back from this desktop's own record, now named for the server.
+      const environmentId = await managedEnvironmentId(page, seeded.targetId)
+      const restarted = await relaunchManagedApp(fixture)
+      await activateManagedWorkspace(restarted, seeded.worktreeId, environmentId)
+      let restored = await readEditorVerdict(restarted, seeded.sessionFilePath, draft)
+      await expect
+        .poll(
+          async () => {
+            restored = await readEditorVerdict(restarted, seeded.sessionFilePath, draft)
+            return restored.verdict
+          },
+          { timeout: 30_000 }
+        )
+        .toBe('present')
+        .catch(() => {})
+      await expect(restarted.locator(VISIBLE_EDITOR).first()).toContainText(
+        `${marker} unsaved line 0`,
+        { timeout: 60_000 }
+      )
+      const profiles = readHostProfiles(fixture)
+      expect(profiles.length, 'no committed server profile was read').toBeGreaterThan(0)
+      const found = profiles.map((state) => findDraft(state, draft, marker))
+      const host: HostVerdict = found.find((entry) => entry.verdict !== 'absent') ?? {
+        verdict: 'absent',
+        where: []
+      }
+      record(
+        testInfo,
+        label,
+        `bytes=${draft.length} sha=${sha256(draft)} editor=${editor.verdict} ` +
+          `restarted=${restored.verdict} host=${host.verdict} ` +
+          `hostAt=${JSON.stringify(host.where)} editorFiles=${editor.detail}`
+      )
+      await restarted.screenshot({ path: testInfo.outputPath(`editor-draft-${label}.png`) })
+      // Asserted after the record, so a miss still says where the draft did and did not go.
+      expect(editor.verdict, `the desktop lost the ${label} draft`).toBe('present')
+      expect(restored.verdict, `a restart lost the ${label} draft`).toBe('present')
+      expect(host.verdict, `the ${label} draft left this desktop`).toBe('absent')
+    })
+  })
+}