diff --git a/src/main/claude/claude-structured-dispatch.test.ts b/src/main/claude/claude-structured-dispatch.test.ts
index 69a107e5d2e..ffdd0a5bbf8 100644
--- a/src/main/claude/claude-structured-dispatch.test.ts
+++ b/src/main/claude/claude-structured-dispatch.test.ts
@@ -16,7 +16,8 @@ function sessionFor(send = vi.fn().mockResolvedValue(undefined)): ClaudeSession
     dispatchWaiters: [],
     options: new Map(),
     reportedOptions: {},
-    events: undefined
+    events: undefined,
+    translator: null
   }
 }
 
diff --git a/src/main/claude/claude-structured-journal-translation.test.ts b/src/main/claude/claude-structured-journal-translation.test.ts
index e29310432a2..d80c0a56889 100644
--- a/src/main/claude/claude-structured-journal-translation.test.ts
+++ b/src/main/claude/claude-structured-journal-translation.test.ts
@@ -5,6 +5,10 @@ import type {
 } from '../../shared/agent-session-journal-types'
 import { agentJournalItemKey } from '../../shared/agent-session-journal-item-key'
 import type { StructuredAgentSessionEventSink } from '../native-chat/agent-session-wire/structured-agent-session-event-sink'
+import {
+  boundInlineText,
+  DEFAULT_JOURNAL_PAYLOAD_LIMITS
+} from '../native-chat/agent-session-journal/journal-payload-bounds'
 import type { ClaudePendingPrompt } from './claude-structured-prompt-replies'
 import { createClaudeJournalTranslator } from './claude-structured-journal-translation'
 
@@ -139,6 +143,19 @@ describe('Claude structured journal translation', () => {
     })
   })
 
+  it('bounds persisted thinking text to the shared journal payload limit', () => {
+    const state = sinkState()
+    const translator = createClaudeJournalTranslator({ sink: state.sink })
+    const thinking = 'considering '.repeat(20_000)
+
+    translator.handle(message('assistant', 'assistant-thinking', [{ type: 'thinking', thinking }]))
+
+    expect(state.items.at(-1)?.body).toEqual({
+      kind: 'status',
+      text: boundInlineText(thinking, DEFAULT_JOURNAL_PAYLOAD_LIMITS).text
+    })
+  })
+
   it('creates addressable approval and multi-question cards and cancels them durably', () => {
     const state = sinkState()
     const bindings: unknown[][] = []
@@ -188,6 +205,31 @@ describe('Claude structured journal translation', () => {
       'Ship?'
     ])
 
+    const multiSelect = prompt({
+      requestId: 'questions-multi',
+      promptKey: 'questions-multi',
+      toolUseId: 'tool-multi',
+      toolName: 'AskUserQuestion',
+      kind: 'question',
+      input: {
+        questions: [
+          {
+            question: 'Libraries?',
+            multiSelect: true,
+            options: [{ label: 'Luxon' }, { label: 'Temporal' }]
+          }
+        ]
+      },
+      questionIds: ['Libraries?']
+    })
+    translator.handle({ type: 'prompt', sessionId: 'orca-session', prompt: multiSelect })
+    expect(state.items.at(-1)?.body).toMatchObject({
+      kind: 'question',
+      question: 'Libraries?\n\nEnter one or more choices separated by commas.',
+      options: [],
+      freeTextQuestionId: 'Libraries?'
+    })
+
     translator.handle({
       type: 'prompt-cancelled',
       sessionId: 'orca-session',
diff --git a/src/main/claude/claude-structured-journal-translation.ts b/src/main/claude/claude-structured-journal-translation.ts
index 5a7d71de94f..f77fe2a87f4 100644
--- a/src/main/claude/claude-structured-journal-translation.ts
+++ b/src/main/claude/claude-structured-journal-translation.ts
@@ -5,6 +5,10 @@ import {
   type AgentSessionDeltaCoalescerDeps
 } from '../native-chat/agent-session-wire/agent-session-delta-coalescer'
 import type { StructuredAgentSessionEventSink } from '../native-chat/agent-session-wire/structured-agent-session-event-sink'
+import {
+  boundInlineText,
+  DEFAULT_JOURNAL_PAYLOAD_LIMITS
+} from '../native-chat/agent-session-journal/journal-payload-bounds'
 import type { ClaudeStructuredSessionEvent } from './claude-structured-session-state'
 import {
   claudeMessageBody,
@@ -187,7 +191,7 @@ export function createClaudeJournalTranslator(
     if (thinking) {
       deps.sink.appendItem(claudeThinkingIdentity(envelope.sessionId, envelope.uuid), {
         kind: 'status',
-        text: thinking
+        text: boundInlineText(thinking, DEFAULT_JOURNAL_PAYLOAD_LIMITS).text
       })
       changed = true
     }
diff --git a/src/main/claude/claude-structured-launch-resolution.test.ts b/src/main/claude/claude-structured-launch-resolution.test.ts
index 4604e308752..3f79ba1066c 100644
--- a/src/main/claude/claude-structured-launch-resolution.test.ts
+++ b/src/main/claude/claude-structured-launch-resolution.test.ts
@@ -29,11 +29,12 @@ function record(overrides: Partial<AgentSessionRecord> = {}): AgentSessionRecord
   } as AgentSessionRecord
 }
 
-function resolverFor(value: AgentSessionRecord | null) {
+function resolverFor(value: AgentSessionRecord | null, resolveEnv?: () => Record<string, string>) {
   return createClaudeStructuredLaunchResolver({
     store: { getRecord: () => value } as unknown as AgentSessionRecordStore,
     resolveWorkspacePath: async (id) => `/repos/${id}`,
-    resolveCommand: () => '/usr/local/bin/claude'
+    resolveCommand: () => '/usr/local/bin/claude',
+    ...(resolveEnv ? { resolveEnv } : {})
   })
 }
 
@@ -83,6 +84,22 @@ describe('claude structured launch resolution', () => {
     expect(launch.args.slice(-2)).toEqual(['--resume', 'provider-current'])
   })
 
+  it('resolves configured environment live without storing it in the session record', async () => {
+    let token = 'first-token'
+    const resolver = resolverFor(record(), () => ({
+      ANTHROPIC_AUTH_TOKEN: token,
+      ANTHROPIC_BASE_URL: 'https://gateway.example.test'
+    }))
+
+    expect((await resolver({ identity: IDENTITY })).env).toEqual({
+      ANTHROPIC_AUTH_TOKEN: 'first-token',
+      ANTHROPIC_BASE_URL: 'https://gateway.example.test'
+    })
+    token = 'rotated-token'
+    expect((await resolver({ identity: IDENTITY })).env?.ANTHROPIC_AUTH_TOKEN).toBe('rotated-token')
+    expect(JSON.stringify(record())).not.toContain('token')
+  })
+
   it('refuses other hosts, WSL, providers, and account-home variables', async () => {
     await expect(
       resolverFor(record({ location: { ...record().location, executionHostId: 'ssh:build' } }))({
diff --git a/src/main/claude/claude-structured-launch-resolution.ts b/src/main/claude/claude-structured-launch-resolution.ts
index 86a90830ce1..bd33dc7f60f 100644
--- a/src/main/claude/claude-structured-launch-resolution.ts
+++ b/src/main/claude/claude-structured-launch-resolution.ts
@@ -38,6 +38,7 @@ export type ClaudeStructuredLaunchResolverDeps = {
   store: AgentSessionRecordStore
   resolveWorkspacePath: (workspaceId: string) => Promise<string>
   resolveCommand?: () => string
+  resolveEnv?: () => Record<string, string>
 }
 
 export function claudeSessionIdForOrcaSession(sessionId: string): string {
@@ -85,6 +86,7 @@ export function createClaudeStructuredLaunchResolver(
       command: spawnCmd,
       args: spawnArgs,
       cwd: await deps.resolveWorkspacePath(record.location.workspaceId),
+      ...(deps.resolveEnv ? { env: deps.resolveEnv() } : {}),
       claudeConfigDir: record.accountHome.path,
       providerSessionId,
       resumeLeafUuid: head?.handle.provider === 'claude' ? head.handle.leafUuid : null,
diff --git a/src/main/claude/claude-structured-prompt-items.ts b/src/main/claude/claude-structured-prompt-items.ts
index e568c0d383f..19a00f3901e 100644
--- a/src/main/claude/claude-structured-prompt-items.ts
+++ b/src/main/claude/claude-structured-prompt-items.ts
@@ -85,6 +85,7 @@ export function claudeQuestionItems(input: {
     const question = claudeRecord(value)
     const questionId = input.prompt.questionIds[index]
     const text = claudeText(question?.question) ?? claudeText(question?.header)
+    const multiSelect = question?.multiSelect === true
     return question && questionId && text
       ? [
           {
@@ -96,8 +97,10 @@ export function claudeQuestionItems(input: {
             }),
             body: {
               kind: 'question',
-              question: text,
-              options: questionOptions(question, questionId),
+              question: multiSelect
+                ? `${text}\n\nEnter one or more choices separated by commas.`
+                : text,
+              options: multiSelect ? [] : questionOptions(question, questionId),
               freeTextQuestionId: questionId,
               resolution: { ...PENDING }
             }
diff --git a/src/main/runtime/claude-structured-session-integration.test.ts b/src/main/runtime/claude-structured-session-integration.test.ts
index 646f55fbbe7..4bef47657b6 100644
--- a/src/main/runtime/claude-structured-session-integration.test.ts
+++ b/src/main/runtime/claude-structured-session-integration.test.ts
@@ -13,6 +13,7 @@ import type {
   openClaudeStreamJsonConnection
 } from '../claude/claude-stream-json-connection'
 import { claudeSessionIdForOrcaSession } from '../claude/claude-structured-launch-resolution'
+import { CLAUDE_SPAWN_TOKEN_ENV } from '../claude/claude-structured-owner-identity'
 import { attachFingerprintFields } from '../native-chat/agent-session-wire/structured-agent-session-attach'
 import { getStructuredAgentSessionHost } from '../native-chat/agent-session-wire/structured-agent-session-registry'
 import type { OrcaRuntimeService } from './orca-runtime'
@@ -244,6 +245,10 @@ beforeEach(async () => {
         resolveWorkspacePath: async (workspaceId) => `/repos/${workspaceId}`,
         resolveCodexCommand: () => '/usr/local/bin/codex',
         resolveClaudeCommand: () => '/usr/local/bin/claude',
+        resolveClaudeLaunchEnv: () => ({
+          ANTHROPIC_AUTH_TOKEN: 'configured-token',
+          ANTHROPIC_BASE_URL: 'https://gateway.example.test'
+        }),
         openClaudeConnection: claude.openConnection
       }).then(() => undefined),
     registerSubscriptionCleanup: (id: string, dispose: () => void) => cleanups.set(id, dispose),
@@ -266,6 +271,12 @@ describe('a structured Claude session over agentSession.*', () => {
     const created = await ok<{ fence: number }>('agentSession.create', createIntentParams())
     expect(claude.live().launch.args).toContain('--session-id')
     expect(claude.live().launch.args).toContain(PROVIDER_SESSION)
+    expect(claude.live().launch.env).toEqual({
+      ANTHROPIC_AUTH_TOKEN: 'configured-token',
+      ANTHROPIC_BASE_URL: 'https://gateway.example.test',
+      CLAUDE_CONFIG_DIR: '/accounts/claude',
+      [CLAUDE_SPAWN_TOKEN_ENV]: expect.any(String)
+    })
     const stream = await subscribe()
 
     const body = { kind: 'message', role: 'user', blocks: [{ type: 'text', text: 'List files' }] }
diff --git a/src/main/runtime/orca-runtime.ts b/src/main/runtime/orca-runtime.ts
index 219642e5ed8..739b7f3d817 100644
--- a/src/main/runtime/orca-runtime.ts
+++ b/src/main/runtime/orca-runtime.ts
@@ -9195,7 +9195,11 @@ export class OrcaRuntimeService {
       // Resolves folder workspaces as well as git worktrees, so a chat session
       // in a plain folder lands in the folder rather than failing to resolve.
       resolveWorkspacePath: async (workspaceId) =>
-        (await this.resolveRuntimeFileTarget(`id:${workspaceId}`)).worktree.path
+        (await this.resolveRuntimeFileTarget(`id:${workspaceId}`)).worktree.path,
+      resolveClaudeLaunchEnv: () => {
+        const settings = this.requireStore().getSettings()
+        return resolveTuiAgentLaunchEnv('claude', settings.agentDefaultEnv)
+      }
     })
   }
 
diff --git a/src/main/runtime/structured-agent-session-runtime.ts b/src/main/runtime/structured-agent-session-runtime.ts
index 9c708039ad2..05c51ee8868 100644
--- a/src/main/runtime/structured-agent-session-runtime.ts
+++ b/src/main/runtime/structured-agent-session-runtime.ts
@@ -42,6 +42,7 @@ export type StructuredAgentSessionRuntimeDeps = {
   resolveWorkspacePath: (workspaceId: string) => Promise<string>
   resolveCodexCommand?: () => string
   resolveClaudeCommand?: () => string
+  resolveClaudeLaunchEnv?: () => Record<string, string>
   /** Transport for the Codex child. Overridden only to drive the whole runtime
    *  against a scripted app-server; production spawns the real one. */
   openCodexConnection?: CodexStructuredSessionAdapterDeps['openConnection']
@@ -104,7 +105,8 @@ async function install(deps: StructuredAgentSessionRuntimeDeps): Promise<Install
     resolveLaunch: createClaudeStructuredLaunchResolver({
       store,
       resolveWorkspacePath: deps.resolveWorkspacePath,
-      ...(deps.resolveClaudeCommand ? { resolveCommand: deps.resolveClaudeCommand } : {})
+      ...(deps.resolveClaudeCommand ? { resolveCommand: deps.resolveClaudeCommand } : {}),
+      ...(deps.resolveClaudeLaunchEnv ? { resolveEnv: deps.resolveClaudeLaunchEnv } : {})
     }),
     ...(deps.openClaudeConnection ? { openConnection: deps.openClaudeConnection } : {}),
     persistHandle: async (observed) => {