diff --git a/cli/src/api/apiSession.test.ts b/cli/src/api/apiSession.test.ts
index 6078e0ee..a44ebc86 100644
--- a/cli/src/api/apiSession.test.ts
+++ b/cli/src/api/apiSession.test.ts
@@ -22,7 +22,16 @@ describe('isExternalUserMessage', () => {
         expect(isExternalUserMessage({ ...baseUserMsg, isSidechain: true })).toBe(false)
     })
 
-    it('returns false when content is an array (tool results)', () => {
+    it('returns true when content is an array of text blocks', () => {
+        expect(
+            isExternalUserMessage({
+                ...baseUserMsg,
+                message: { role: 'user', content: [{ type: 'text', text: 'hello array' }] },
+            } as never)
+        ).toBe(true)
+    })
+
+    it('returns false when content is a non-text array (tool results)', () => {
         expect(
             isExternalUserMessage({
                 ...baseUserMsg,
diff --git a/cli/src/api/apiSession.ts b/cli/src/api/apiSession.ts
index 398f13c0..10992dc8 100644
--- a/cli/src/api/apiSession.ts
+++ b/cli/src/api/apiSession.ts
@@ -48,6 +48,28 @@ const SYSTEM_INJECTION_PREFIXES = [
     '<system-reminder>',
 ]
 
+function extractRawUserTextContent(content: unknown): string | null {
+    if (typeof content === 'string') {
+        return content
+    }
+
+    if (!Array.isArray(content)) {
+        return null
+    }
+
+    const parts = content
+        .map((block) => {
+            if (!block || typeof block !== 'object' || Array.isArray(block)) return null
+            const record = block as Record<string, unknown>
+            return record.type === 'text' && typeof record.text === 'string'
+                ? record.text
+                : null
+        })
+        .filter((text): text is string => text !== null)
+
+    return parts.length > 0 ? parts.join('\n') : null
+}
+
 /**
  * Returns true if a JSONL message should be classified as a user-role message
  * (i.e., text typed by a real human) rather than an agent-role message.
@@ -58,13 +80,14 @@ const SYSTEM_INJECTION_PREFIXES = [
  * genuine user messages, so the only reliable signal is the message content
  * itself: injected messages always start with a well-known XML tag.
  */
-export function isExternalUserMessage(body: RawJSONLines): body is Extract<RawJSONLines, { type: 'user' }> & { message: { content: string } } {
+export function isExternalUserMessage(body: RawJSONLines): body is Extract<RawJSONLines, { type: 'user' }> {
     if (body.type !== 'user') return false
-    if (typeof body.message.content !== 'string') return false
+    const text = extractRawUserTextContent(body.message.content)
+    if (text === null) return false
     if (body.isSidechain === true) return false
     if (body.isMeta === true) return false
 
-    const trimmed = body.message.content.trimStart()
+    const trimmed = text.trimStart()
     for (const prefix of SYSTEM_INJECTION_PREFIXES) {
         if (trimmed.startsWith(prefix)) return false
     }
@@ -440,7 +463,7 @@ export class ApiSessionClient extends EventEmitter {
                 role: 'user',
                 content: {
                     type: 'text',
-                    text: body.message.content
+                    text: extractRawUserTextContent(body.message.content) ?? ''
                 },
                 meta: {
                     sentFrom: 'cli'
diff --git a/hub/src/sync/sessionModel.test.ts b/hub/src/sync/sessionModel.test.ts
index 49ef20bf..6e038a1d 100644
--- a/hub/src/sync/sessionModel.test.ts
+++ b/hub/src/sync/sessionModel.test.ts
@@ -1034,6 +1034,54 @@ describe('session model', () => {
         }
     })
 
+    it('recovers first user message from stored Claude user output events', () => {
+        const store = new Store(':memory:')
+        const engine = new SyncEngine(
+            store,
+            {} as never,
+            new RpcRegistry(),
+            { broadcast() {} } as never
+        )
+
+        try {
+            const session = engine.getOrCreateSession(
+                'local-resume-first-claude-output',
+                {
+                    path: '/tmp/project',
+                    host: 'localhost',
+                    machineId: 'machine-1',
+                    flavor: 'claude',
+                    claudeSessionId: '11111111-1111-4111-8111-111111111111',
+                    name: 'Generated title'
+                },
+                null,
+                'default'
+            )
+            store.messages.addMessage(session.id, {
+                role: 'agent',
+                content: {
+                    type: 'output',
+                    data: {
+                        type: 'user',
+                        message: {
+                            role: 'user',
+                            content: [{ type: 'text', text: 'First Claude prompt' }]
+                        }
+                    }
+                }
+            })
+
+            const sessions = engine.listLocalResumableSessions('default', { machineId: 'machine-1' })
+
+            expect(sessions.find((item) => item.sessionId === session.id)).toMatchObject({
+                name: 'Generated title',
+                firstUserMessage: 'First Claude prompt'
+            })
+        } finally {
+            engine.stop()
+        }
+    })
+
     it('local handoff succeeds immediately for inactive sessions', async () => {
         const store = new Store(':memory:')
         const engine = new SyncEngine(
diff --git a/hub/src/sync/syncEngine.ts b/hub/src/sync/syncEngine.ts
index c4bff8b7..76d56e73 100644
--- a/hub/src/sync/syncEngine.ts
+++ b/hub/src/sync/syncEngine.ts
@@ -98,6 +98,19 @@ function extractUserMessageText(content: unknown): string | undefined {
     return undefined
 }
 
+function extractClaudeUserMessageTextFromAgentOutput(content: unknown): string | undefined {
+    const record = asRecord(content)
+    if (record?.type !== 'output') return undefined
+
+    const data = asRecord(record.data)
+    if (data?.type !== 'user') return undefined
+
+    const message = asRecord(data.message)
+    if (message?.role !== 'user') return undefined
+
+    return extractUserMessageText(message.content)
+}
+
 export class SyncEngine {
     private readonly eventPublisher: EventPublisher
     private readonly sessionCache: SessionCache
@@ -569,9 +582,11 @@ export class SyncEngine {
     private resolveFirstUserMessage(sessionId: string): string | undefined {
         for (const message of this.store.messages.getFirstMessages(sessionId, 50)) {
             const roleWrapped = unwrapRoleWrappedRecordEnvelope(message.content)
-            if (roleWrapped?.role !== 'user') continue
-
-            const text = extractUserMessageText(roleWrapped.content)
+            const text = roleWrapped?.role === 'user'
+                ? extractUserMessageText(roleWrapped.content)
+                : roleWrapped?.role === 'agent'
+                    ? extractClaudeUserMessageTextFromAgentOutput(roleWrapped.content)
+                    : undefined
             if (text) return text
         }