diff --git a/hub/src/sync/permissionModePersistence.test.ts b/hub/src/sync/permissionModePersistence.test.ts
new file mode 100644
index 000000000..821c02ef2
--- /dev/null
+++ b/hub/src/sync/permissionModePersistence.test.ts
@@ -0,0 +1,97 @@
+import { describe, expect, it } from 'bun:test'
+import { Store } from '../store'
+import { SyncEngine } from './syncEngine'
+
+function createEngine(store?: Store): SyncEngine {
+    const engine = new SyncEngine(
+        store ?? new Store(':memory:'),
+        {
+            of: () => ({
+                to: () => ({
+                    emit: () => {}
+                })
+            })
+        } as never,
+        {} as never,
+        {
+            broadcast: () => {}
+        } as never
+    )
+    engine.stop()
+    return engine
+}
+
+describe('permission mode persistence', () => {
+    it('restores saved permission mode after reloading sessions from the store', () => {
+        const store = new Store(':memory:')
+        const engine = createEngine(store)
+
+        const session = engine.getOrCreateSession(
+            'permission-mode-persist',
+            { path: '/tmp/project', host: 'localhost' },
+            { requests: {}, completedRequests: {} },
+            'default'
+        )
+
+        engine.handleSessionAlive({
+            sid: session.id,
+            time: Date.now(),
+            thinking: false,
+            permissionMode: 'yolo'
+        })
+
+        const reloadedEngine = createEngine(store)
+        const reloadedSession = reloadedEngine.getSession(session.id)
+
+        expect(reloadedSession?.metadata?.preferredPermissionMode).toBe('yolo')
+        expect(reloadedSession?.permissionMode).toBe('yolo')
+    })
+
+    it('reapplies the previous permission mode when resuming an archived session', async () => {
+        const engine = createEngine()
+
+        const machine = engine.getOrCreateMachine(
+            'machine-1',
+            { host: 'localhost', platform: 'linux', happyCliVersion: '0.1.0' },
+            null,
+            'default'
+        )
+        engine.handleMachineAlive({ machineId: machine.id, time: Date.now() })
+
+        const session = engine.getOrCreateSession(
+            'resume-permission-mode',
+            {
+                path: '/tmp/project',
+                host: 'localhost',
+                machineId: machine.id,
+                flavor: 'codex',
+                codexSessionId: 'resume-token',
+                preferredPermissionMode: 'yolo'
+            },
+            { requests: {}, completedRequests: {} },
+            'default'
+        )
+
+        const calls: Array<{ type: 'spawn' } | { type: 'config'; sessionId: string; permissionMode?: string }> = []
+        const spawnSession = async () => {
+            calls.push({ type: 'spawn' })
+            return { type: 'success' as const, sessionId: session.id }
+        }
+        const requestSessionConfig = async (sessionId: string, config: { permissionMode?: string }) => {
+            calls.push({ type: 'config', sessionId, permissionMode: config.permissionMode })
+            return { applied: { permissionMode: config.permissionMode } }
+        }
+
+        ;(engine as any).rpcGateway = {
+            spawnSession,
+            requestSessionConfig
+        }
+        ;(engine as any).waitForSessionActive = async () => true
+
+        const result = await engine.resumeSession(session.id, 'default')
+
+        expect(result).toEqual({ type: 'success', sessionId: session.id })
+        expect(calls).toContainEqual({ type: 'spawn' })
+        expect(calls).toContainEqual({ type: 'config', sessionId: session.id, permissionMode: 'yolo' })
+    })
+})
diff --git a/hub/src/sync/sessionCache.ts b/hub/src/sync/sessionCache.ts
index c9a0c5490..3c298445b 100644
--- a/hub/src/sync/sessionCache.ts
+++ b/hub/src/sync/sessionCache.ts
@@ -126,7 +126,7 @@ export class SessionCache {
             thinkingAt: existing?.thinkingAt ?? 0,
             todos,
             teamState,
-            permissionMode: existing?.permissionMode,
+            permissionMode: existing?.permissionMode ?? metadata?.preferredPermissionMode,
             modelMode: existing?.modelMode
         }
 
@@ -167,6 +167,7 @@ export class SessionCache {
         session.thinkingAt = t
         if (payload.permissionMode !== undefined) {
             session.permissionMode = payload.permissionMode
+            this.persistPreferredPermissionMode(session, payload.permissionMode)
         }
         if (payload.modelMode !== undefined) {
             session.modelMode = payload.modelMode
@@ -233,6 +234,7 @@ export class SessionCache {
 
         if (config.permissionMode !== undefined) {
             session.permissionMode = config.permissionMode
+            this.persistPreferredPermissionMode(session, config.permissionMode)
         }
         if (config.modelMode !== undefined) {
             session.modelMode = config.modelMode
@@ -398,7 +400,39 @@ export class SessionCache {
             merged.host = oldObj.host
             changed = true
         }
+        if (typeof oldObj.preferredPermissionMode === 'string' && typeof newObj.preferredPermissionMode !== 'string') {
+            merged.preferredPermissionMode = oldObj.preferredPermissionMode
+            changed = true
+        }
 
         return changed ? merged : newMetadata
     }
+
+    private persistPreferredPermissionMode(session: Session, permissionMode: PermissionMode): void {
+        const currentMetadata = session.metadata
+        if (!currentMetadata || currentMetadata.preferredPermissionMode === permissionMode) {
+            return
+        }
+
+        const nextMetadata = { ...currentMetadata, preferredPermissionMode: permissionMode }
+        const result = this.store.sessions.updateSessionMetadata(
+            session.id,
+            nextMetadata,
+            session.metadataVersion,
+            session.namespace,
+            { touchUpdatedAt: false }
+        )
+
+        if (result.result === 'error') {
+            return
+        }
+
+        const parsed = MetadataSchema.safeParse(result.value)
+        if (!parsed.success) {
+            return
+        }
+
+        session.metadata = parsed.data
+        session.metadataVersion = result.version
+    }
 }
diff --git a/hub/src/sync/syncEngine.ts b/hub/src/sync/syncEngine.ts
index da497556d..607a5a1cf 100644
--- a/hub/src/sync/syncEngine.ts
+++ b/hub/src/sync/syncEngine.ts
@@ -329,6 +329,7 @@ export class SyncEngine {
         if (!metadata || typeof metadata.path !== 'string') {
             return { type: 'error', message: 'Session metadata missing path', code: 'resume_unavailable' }
         }
+        const preferredPermissionMode = session.permissionMode ?? metadata.preferredPermissionMode
 
         const flavor = metadata.flavor === 'codex' || metadata.flavor === 'gemini' || metadata.flavor === 'opencode' || metadata.flavor === 'cursor'
             ? metadata.flavor
@@ -388,6 +389,15 @@ export class SyncEngine {
             return { type: 'error', message: 'Session failed to become active', code: 'resume_failed' }
         }
 
+        if (preferredPermissionMode !== undefined) {
+            try {
+                await this.applySessionConfig(spawnResult.sessionId, { permissionMode: preferredPermissionMode })
+            } catch (error) {
+                const message = error instanceof Error ? error.message : 'Failed to restore permission mode'
+                return { type: 'error', message, code: 'resume_failed' }
+            }
+        }
+
         if (spawnResult.sessionId !== access.sessionId) {
             try {
                 await this.sessionCache.mergeSessions(access.sessionId, spawnResult.sessionId, namespace)
diff --git a/shared/src/schemas.ts b/shared/src/schemas.ts
index 5fc5c1bb7..d470aac12 100644
--- a/shared/src/schemas.ts
+++ b/shared/src/schemas.ts
@@ -45,6 +45,7 @@ export const MetadataSchema = z.object({
     lifecycleStateSince: z.number().optional(),
     archivedBy: z.string().optional(),
     archiveReason: z.string().optional(),
+    preferredPermissionMode: PermissionModeSchema.optional(),
     flavor: z.string().nullish(),
     worktree: WorktreeMetadataSchema.optional()
 })