diff --git a/apps/cli/src/ai/agent-stream-runner.test.ts b/apps/cli/src/ai/agent-stream-runner.test.ts
index 6958191e..f9d974c7 100644
--- a/apps/cli/src/ai/agent-stream-runner.test.ts
+++ b/apps/cli/src/ai/agent-stream-runner.test.ts
@@ -40,6 +40,17 @@ describe('CLI chart capability tool filtering', () => {
     assert.ok(!toolNames.includes('execute_sql'))
   })
 
+  it('accepts legacy session tool names in assistant allowlists', () => {
+    const allowedToolSet = getAllowedToolSet(false, ['get_session_summaries'])
+
+    assert.ok(allowedToolSet instanceof Set)
+
+    const toolNames = getAvailableToolDefs(false, allowedToolSet).map((tool) => tool.name)
+
+    assert.ok(toolNames.includes('get_segment_summaries'))
+    assert.ok(!toolNames.includes('get_session_summaries'))
+  })
+
   it('preserves an empty assistant allowlist instead of treating it as unrestricted', () => {
     const allowedToolSet = getAllowedToolSet(false, [])
 
diff --git a/apps/cli/src/ai/agent-stream-runner.ts b/apps/cli/src/ai/agent-stream-runner.ts
index e9e92039..ed9a0cfb 100644
--- a/apps/cli/src/ai/agent-stream-runner.ts
+++ b/apps/cli/src/ai/agent-stream-runner.ts
@@ -14,7 +14,7 @@ import {
   getSkillConfigWithBuiltinChart,
   resolveChartRuntimeForRequest,
 } from '@openchatlab/node-runtime'
-import { getChatOverview } from '@openchatlab/core'
+import { getChatOverview, normalizeBuiltinToolNames } from '@openchatlab/core'
 import type { DataSnapshot } from '@openchatlab/node-runtime'
 import type { AgentStreamRequest } from '@openchatlab/http-routes'
 import { AGENT_TOOL_REGISTRY } from '@openchatlab/tools'
@@ -54,9 +54,9 @@ export function getAllowedToolSet(
   allowedBuiltinTools?: readonly string[]
 ): Set<string> | null {
   if (isChartCapability) {
-    return new Set(allowedBuiltinTools)
+    return new Set(normalizeBuiltinToolNames(allowedBuiltinTools ?? []))
   }
-  return allowedBuiltinTools === undefined ? null : new Set(allowedBuiltinTools)
+  return allowedBuiltinTools === undefined ? null : new Set(normalizeBuiltinToolNames(allowedBuiltinTools))
 }
 
 export function createCliRunAgentStream(
diff --git a/apps/cli/src/ai/chat-command.test.ts b/apps/cli/src/ai/chat-command.test.ts
index ca6b1a5b..c2b91a1c 100644
--- a/apps/cli/src/ai/chat-command.test.ts
+++ b/apps/cli/src/ai/chat-command.test.ts
@@ -1,8 +1,9 @@
 import { describe, it } from 'node:test'
 import assert from 'node:assert/strict'
+import { Readable } from 'node:stream'
 import { Writable } from 'node:stream'
 import type { AIChatManager, DatabaseManager } from '@openchatlab/node-runtime'
-import { resolveAIChatTarget, runChatTurn } from './chat-command'
+import { resolveAIChatTarget, runChatCommand, runChatTurn } from './chat-command'
 
 function createDbManager(sessionIds: string[]): DatabaseManager {
   return {
@@ -11,9 +12,11 @@ function createDbManager(sessionIds: string[]): DatabaseManager {
   } as unknown as DatabaseManager
 }
 
-function createAIChatManager(existing: Array<{ id: string; sessionId: string }> = []): AIChatManager {
+function createAIChatManager(
+  existing: Array<{ id: string; sessionId: string; assistantId?: string }> = []
+): AIChatManager {
   const chats = new Map<string, { id: string; sessionId: string; title: string | null; assistantId: string }>(
-    existing.map((chat) => [chat.id, { ...chat, title: null, assistantId: 'general_cn' }])
+    existing.map((chat) => [chat.id, { ...chat, title: null, assistantId: chat.assistantId ?? 'general_cn' }])
   )
   const messages: Array<{ aiChatId: string; role: string; content: string }> = []
 
@@ -35,9 +38,12 @@ function createAIChatManager(existing: Array<{ id: string; sessionId: string }>
 
 class MemoryWritable extends Writable {
   chunks: string[] = []
+  onChunk?: (text: string) => void
 
   _write(chunk: Buffer | string, _encoding: BufferEncoding, callback: (error?: Error | null) => void): void {
-    this.chunks.push(String(chunk))
+    const text = String(chunk)
+    this.chunks.push(text)
+    this.onChunk?.(text)
     callback()
   }
 
@@ -46,6 +52,28 @@ class MemoryWritable extends Writable {
   }
 }
 
+class PromptDrivenReadable extends Readable {
+  private nextLines: string[]
+
+  constructor(lines: string[]) {
+    super()
+    this.nextLines = lines
+  }
+
+  _read(): void {
+    // Input is pushed when the CLI writes a prompt.
+  }
+
+  pushNext(): void {
+    const line = this.nextLines.shift()
+    if (line === undefined) {
+      this.push(null)
+      return
+    }
+    this.push(`${line}\n`)
+  }
+}
+
 describe('resolveAIChatTarget', () => {
   it('creates a new AI chat for an explicit session id', () => {
     const target = resolveAIChatTarget(
@@ -67,7 +95,12 @@ describe('resolveAIChatTarget', () => {
       }
     )
 
-    assert.deepEqual(target, { sessionId: 'session-1', aiChatId: 'ai-chat-1', created: false })
+    assert.deepEqual(target, {
+      sessionId: 'session-1',
+      aiChatId: 'ai-chat-1',
+      assistantId: 'general_cn',
+      created: false,
+    })
   })
 
   it('rejects mismatched explicit session id and aiChatId', () => {
@@ -89,6 +122,7 @@ describe('runChatTurn', () => {
   it('collects streamed answer and persists user and assistant messages', async () => {
     const stdout = new MemoryWritable()
     const aiChatManager = createAIChatManager()
+    let streamedAssistantId: string | undefined
     const result = await runChatTurn(
       { sessionId: 'session-1', question: 'hello', json: true },
       {
@@ -96,7 +130,8 @@ describe('runChatTurn', () => {
         pathProvider: {} as never,
         aiChatManager,
         stdout,
-        createRunAgentStream: () => async (_params, onEvent) => {
+        createRunAgentStream: () => async (params, onEvent) => {
+          streamedAssistantId = params.assistantId
           onEvent({ type: 'content', content: 'hi' })
           onEvent({
             type: 'done',
@@ -111,10 +146,101 @@ describe('runChatTurn', () => {
     assert.equal(result.aiChatId, 'ai_chat_1')
     assert.equal(result.answer, 'hi')
     assert.equal(result.usage.tokenUsage?.totalTokens, 2)
+    assert.equal(streamedAssistantId, 'general_cn')
     assert.equal(stdout.text(), '')
     assert.deepEqual((aiChatManager as unknown as { __messages: unknown[] }).__messages, [
       { aiChatId: 'ai_chat_1', role: 'user', content: 'hello' },
       { aiChatId: 'ai_chat_1', role: 'assistant', content: 'hi' },
     ])
   })
+
+  it('fails the turn and does not persist messages when the agent stream reports an error', async () => {
+    const stdout = new MemoryWritable()
+    const aiChatManager = createAIChatManager()
+
+    await assert.rejects(
+      () =>
+        runChatTurn(
+          { sessionId: 'session-1', question: 'hello', json: true },
+          {
+            dbManager: createDbManager(['session-1']),
+            pathProvider: {} as never,
+            aiChatManager,
+            stdout,
+            createRunAgentStream: () => async (_params, onEvent) => {
+              onEvent({ type: 'error', error: { name: 'ConfigError', message: 'LLM service not configured' } })
+              onEvent({ type: 'done', isFinished: true })
+            },
+          }
+        ),
+      /LLM service not configured/
+    )
+
+    assert.equal(stdout.text(), '')
+    assert.deepEqual((aiChatManager as unknown as { __messages: unknown[] }).__messages, [])
+  })
+
+  it('passes the resolved AI chat assistant id into the agent stream', async () => {
+    const stdout = new MemoryWritable()
+    const aiChatManager = createAIChatManager([
+      { id: 'ai-chat-1', sessionId: 'session-1', assistantId: 'custom_assistant' },
+    ])
+    let streamedAssistantId: string | undefined
+
+    await runChatTurn(
+      { aiChatId: 'ai-chat-1', question: 'hello', json: true },
+      {
+        dbManager: createDbManager(['session-1']),
+        pathProvider: {} as never,
+        aiChatManager,
+        stdout,
+        createRunAgentStream: () => async (params, onEvent) => {
+          streamedAssistantId = params.assistantId
+          onEvent({ type: 'content', content: 'hi' })
+          onEvent({ type: 'done', isFinished: true })
+        },
+      }
+    )
+
+    assert.equal(streamedAssistantId, 'custom_assistant')
+  })
+})
+
+describe('runChatCommand', () => {
+  it('keeps interactive mode alive after a single failed turn', async () => {
+    const stdout = new MemoryWritable()
+    const stderr = new MemoryWritable()
+    const stdin = new PromptDrivenReadable(['fail', 'recover', 'exit'])
+    const aiChatManager = createAIChatManager()
+    stdout.onChunk = (text) => {
+      if (text.includes('chatlab> ')) stdin.pushNext()
+    }
+
+    const command = runChatCommand(
+      { sessionId: 'session-1' },
+      {
+        dbManager: createDbManager(['session-1']),
+        pathProvider: {} as never,
+        aiChatManager,
+        stdout,
+        stderr,
+        stdin,
+        createRunAgentStream: () => async (params, onEvent) => {
+          if (params.userMessage === 'fail') {
+            throw new Error('temporary failure')
+          }
+          onEvent({ type: 'content', content: 'recovered' })
+          onEvent({ type: 'done', isFinished: true })
+        },
+      }
+    )
+    await command
+
+    assert.match(stderr.text(), /temporary failure/)
+    assert.match(stdout.text(), /recovered/)
+    assert.deepEqual((aiChatManager as unknown as { __messages: unknown[] }).__messages, [
+      { aiChatId: 'ai_chat_2', role: 'user', content: 'recover' },
+      { aiChatId: 'ai_chat_2', role: 'assistant', content: 'recovered' },
+    ])
+  })
 })
diff --git a/apps/cli/src/ai/chat-command.ts b/apps/cli/src/ai/chat-command.ts
index 750fb917..81e02525 100644
--- a/apps/cli/src/ai/chat-command.ts
+++ b/apps/cli/src/ai/chat-command.ts
@@ -26,6 +26,7 @@ export interface ChatCommandDeps {
 export interface ResolvedAIChatTarget {
   sessionId: string
   aiChatId: string
+  assistantId: string
   created: boolean
 }
 
@@ -50,6 +51,21 @@ function buildTitle(question?: string): string {
   return trimmed.length > 50 ? `${trimmed.slice(0, 50)}...` : trimmed
 }
 
+function createAgentStreamError(error: unknown): Error {
+  if (error instanceof Error) return error
+  if (typeof error === 'string' && error) return new Error(error)
+  if (typeof error === 'object' && error !== null) {
+    const record = error as { name?: unknown; message?: unknown; stack?: unknown }
+    const streamError = new Error(
+      typeof record.message === 'string' && record.message ? record.message : 'Agent stream failed'
+    )
+    if (typeof record.name === 'string' && record.name) streamError.name = record.name
+    if (typeof record.stack === 'string' && record.stack) streamError.stack = record.stack
+    return streamError
+  }
+  return new Error('Agent stream failed')
+}
+
 function resolveSingleSessionId(dbManager: DatabaseManager): string {
   const sessionIds = dbManager.listSessionIds()
   if (sessionIds.length === 1) return sessionIds[0]!
@@ -79,13 +95,13 @@ export function resolveAIChatTarget(
       throw new Error(`AI chat ${options.aiChatId} belongs to session ${aiChat.sessionId}, not ${options.sessionId}`)
     }
     assertSessionExists(deps.dbManager, aiChat.sessionId)
-    return { sessionId: aiChat.sessionId, aiChatId: aiChat.id, created: false }
+    return { sessionId: aiChat.sessionId, aiChatId: aiChat.id, assistantId: aiChat.assistantId, created: false }
   }
 
   const sessionId = options.sessionId ?? resolveSingleSessionId(deps.dbManager)
   assertSessionExists(deps.dbManager, sessionId)
   const aiChat = deps.aiChatManager.createAIChat(sessionId, buildTitle(options.question), 'general_cn')
-  return { sessionId, aiChatId: aiChat.id, created: true }
+  return { sessionId, aiChatId: aiChat.id, assistantId: aiChat.assistantId, created: true }
 }
 
 export async function runChatTurn(
@@ -98,6 +114,7 @@ export async function runChatTurn(
   const startedAt = Date.now()
   let answer = ''
   let tokenUsage: TokenUsageData | null = null
+  let streamError: Error | null = null
 
   const runAgentStream = (deps.createRunAgentStream ?? createCliRunAgentStream)(deps.dbManager, deps.aiChatManager)
 
@@ -106,10 +123,15 @@ export async function runChatTurn(
       userMessage: options.question,
       sessionId: target.sessionId,
       aiChatId: target.aiChatId,
+      assistantId: target.assistantId,
       chatType: 'group',
       locale: options.locale ?? 'zh-CN',
     },
     (chunk: AgentStreamChunk) => {
+      if (chunk.type === 'error') {
+        streamError = createAgentStreamError(chunk.error)
+        return
+      }
       if (chunk.type === 'content' && chunk.content) {
         answer += chunk.content
         if (!options.json && options.stream !== false) write(stdout, chunk.content)
@@ -121,6 +143,8 @@ export async function runChatTurn(
     new AbortController().signal
   )
 
+  if (streamError) throw streamError
+
   if (!options.json && options.stream !== false && answer && !answer.endsWith('\n')) {
     write(stdout, '\n')
   }
@@ -172,12 +196,13 @@ export async function runChatCommand(options: ChatCommandOptions, deps: ChatComm
     while (true) {
       const question = (await rl.question('chatlab> ')).trim()
       if (!question || question === 'exit' || question === 'quit') break
-      const result = await runChatTurn({ ...options, aiChatId, question, json: false, stream: true }, deps)
-      aiChatId = result.aiChatId
+      try {
+        const result = await runChatTurn({ ...options, aiChatId, question, json: false, stream: true }, deps)
+        aiChatId = result.aiChatId
+      } catch (error) {
+        write(stderr, `${error instanceof Error ? error.message : String(error)}\n`)
+      }
     }
-  } catch (error) {
-    write(stderr, `${error instanceof Error ? error.message : String(error)}\n`)
-    throw error
   } finally {
     rl.close()
   }
diff --git a/apps/desktop/main/ai/tools/tool-filter.test.ts b/apps/desktop/main/ai/tools/tool-filter.test.ts
index 7830c379..430bc9e6 100644
--- a/apps/desktop/main/ai/tools/tool-filter.test.ts
+++ b/apps/desktop/main/ai/tools/tool-filter.test.ts
@@ -13,4 +13,8 @@ describe('Electron analysis tool filtering', () => {
     assert.equal(isAnalysisToolAllowed('keyword_frequency', ['keyword_frequency']), true)
     assert.equal(isAnalysisToolAllowed('execute_sql', ['keyword_frequency']), false)
   })
+
+  it('accepts legacy session tool names in assistant allowlists', () => {
+    assert.equal(isAnalysisToolAllowed('get_segment_summaries', ['get_session_summaries']), true)
+  })
 })
diff --git a/apps/desktop/main/ai/tools/tool-filter.ts b/apps/desktop/main/ai/tools/tool-filter.ts
index 79407371..edec5af7 100644
--- a/apps/desktop/main/ai/tools/tool-filter.ts
+++ b/apps/desktop/main/ai/tools/tool-filter.ts
@@ -1,3 +1,5 @@
+import { normalizeBuiltinToolNames } from '@openchatlab/core'
+
 export function isAnalysisToolAllowed(toolName: string, allowedTools?: readonly string[] | null): boolean {
-  return !!allowedTools?.includes(toolName)
+  return !!allowedTools && normalizeBuiltinToolNames(allowedTools).includes(toolName)
 }
diff --git a/packages/core/src/ai/index.ts b/packages/core/src/ai/index.ts
index c6d4f0bc..d3c3196a 100644
--- a/packages/core/src/ai/index.ts
+++ b/packages/core/src/ai/index.ts
@@ -4,7 +4,7 @@
 
 // 内置工具目录
 export type { ToolCategory, BuiltinToolCatalogEntry } from './tool-catalog'
-export { BUILTIN_TOOL_CATALOG } from './tool-catalog'
+export { BUILTIN_TOOL_CATALOG, normalizeBuiltinToolName, normalizeBuiltinToolNames } from './tool-catalog'
 export { CHART_CAPABILITY_SKILL_ID } from './chart-capability'
 
 // LLM 模型系统类型
diff --git a/packages/core/src/ai/tool-catalog.ts b/packages/core/src/ai/tool-catalog.ts
index ca1c4520..8f07240c 100644
--- a/packages/core/src/ai/tool-catalog.ts
+++ b/packages/core/src/ai/tool-catalog.ts
@@ -12,6 +12,20 @@ export interface BuiltinToolCatalogEntry {
   category: ToolCategory
 }
 
+const LEGACY_BUILTIN_TOOL_NAME_ALIASES: Record<string, string> = {
+  search_sessions: 'search_segments',
+  get_session_messages: 'get_segment_messages',
+  get_session_summaries: 'get_segment_summaries',
+}
+
+export function normalizeBuiltinToolName(toolName: string): string {
+  return LEGACY_BUILTIN_TOOL_NAME_ALIASES[toolName] ?? toolName
+}
+
+export function normalizeBuiltinToolNames(toolNames: readonly string[]): string[] {
+  return Array.from(new Set(toolNames.map(normalizeBuiltinToolName)))
+}
+
 export const BUILTIN_TOOL_CATALOG: BuiltinToolCatalogEntry[] = [
   // Core 工具
   { name: 'get_chat_overview', category: 'core' },
diff --git a/packages/core/src/index.ts b/packages/core/src/index.ts
index 8fd62cf9..7dc618d3 100644
--- a/packages/core/src/index.ts
+++ b/packages/core/src/index.ts
@@ -230,7 +230,7 @@ export type {
 
 // AI（内置工具目录、LLM 模型系统等静态数据）
 export type { ToolCategory, BuiltinToolCatalogEntry } from './ai'
-export { BUILTIN_TOOL_CATALOG } from './ai'
+export { BUILTIN_TOOL_CATALOG, normalizeBuiltinToolName, normalizeBuiltinToolNames } from './ai'
 export type {
   ProviderKind,
   ProviderDefinition,
diff --git a/packages/core/src/query/advanced/relationship.ts b/packages/core/src/query/advanced/relationship.ts
index 4b55f1de..ae7b7a33 100644
--- a/packages/core/src/query/advanced/relationship.ts
+++ b/packages/core/src/query/advanced/relationship.ts
@@ -102,9 +102,9 @@ export function getRelationshipStats(
 
   const whereClause = timeConditions.length > 0 ? `WHERE ${timeConditions.join(' AND ')}` : ''
 
-  const sessionRows = db
+  const segmentRows = db
     .prepare(
-      `SELECT cs.id AS session_id, cs.start_ts, cs.end_ts,
+      `SELECT cs.id AS segment_id, cs.start_ts, cs.end_ts,
               (SELECT m.sender_id FROM message_context mc JOIN message m ON m.id = mc.message_id
                WHERE mc.segment_id = cs.id ORDER BY m.ts ASC, m.id ASC LIMIT 1) AS initiator_id,
               (SELECT m.sender_id FROM message_context mc JOIN message m ON m.id = mc.message_id
@@ -112,7 +112,7 @@ export function getRelationshipStats(
        FROM segment cs ${whereClause} ORDER BY cs.start_ts ASC`
     )
     .all(...params) as Array<{
-    session_id: number
+    segment_id: number
     start_ts: number
     end_ts: number
     initiator_id: number | null
@@ -135,7 +135,7 @@ export function getRelationshipStats(
   let totalIceBreaks = 0
   let prevEndTs: number | null = null
 
-  for (const row of sessionRows) {
+  for (const row of segmentRows) {
     const month = toLocalMonth(row.start_ts)
     if (!monthMap.has(month)) monthMap.set(month, { initiateMap: new Map(), closeMap: new Map(), totalSessions: 0 })
     const ms = monthMap.get(month)!
@@ -192,13 +192,13 @@ export function getRelationshipStats(
     }
   }
 
-  const sessionIdList = sessionRows.map((r) => r.session_id)
-  const msgStats = queryMessageLevelStats(db, sessionIdList, memberNames, perseveranceThreshold)
+  const segmentIdList = segmentRows.map((r) => r.segment_id)
+  const msgStats = queryMessageLevelStats(db, segmentIdList, memberNames, perseveranceThreshold)
 
   return {
     months,
     members,
-    totalSessions: sessionRows.length,
+    totalSessions: segmentRows.length,
     hasSessionIndex: true,
     iceBreakers,
     totalIceBreaks,
@@ -209,7 +209,7 @@ export function getRelationshipStats(
 
 function queryMessageLevelStats(
   db: DatabaseAdapter,
-  sessionIds: number[],
+  segmentIds: number[],
   memberNames: Map<number, string>,
   perseveranceThreshold: number
 ): {
@@ -226,7 +226,7 @@ function queryMessageLevelStats(
     monthlyResponseLatency: [],
     monthlyPerseverance: [],
   }
-  if (sessionIds.length === 0) return empty
+  if (segmentIds.length === 0) return empty
 
   const BATCH_SIZE = 500
   const responseTotals = new Map<number, { sum: number; count: number }>()
@@ -234,8 +234,8 @@ function queryMessageLevelStats(
   const monthlyRespMap = new Map<string, Map<number, { sum: number; count: number }>>()
   const monthlyDtMap = new Map<string, Map<number, number>>()
 
-  for (let i = 0; i < sessionIds.length; i += BATCH_SIZE) {
-    const batch = sessionIds.slice(i, i + BATCH_SIZE)
+  for (let i = 0; i < segmentIds.length; i += BATCH_SIZE) {
+    const batch = segmentIds.slice(i, i + BATCH_SIZE)
     const placeholders = batch.map(() => '?').join(',')
 
     const latencyRows = db
diff --git a/packages/node-runtime/src/ai/__tests__/assistant-parser.test.ts b/packages/node-runtime/src/ai/__tests__/assistant-parser.test.ts
new file mode 100644
index 00000000..81b2d114
--- /dev/null
+++ b/packages/node-runtime/src/ai/__tests__/assistant-parser.test.ts
@@ -0,0 +1,29 @@
+import { describe, it } from 'node:test'
+import assert from 'node:assert/strict'
+import { parseAssistantFile } from '../assistant-parser'
+
+describe('parseAssistantFile', () => {
+  it('normalizes legacy session tool names in allowedBuiltinTools', () => {
+    const config = parseAssistantFile(
+      `---
+id: legacy_tools
+name: Legacy Tools
+allowedBuiltinTools:
+  - search_sessions
+  - get_session_messages
+  - get_session_summaries
+  - keyword_frequency
+---
+Use selected tools.`,
+      'legacy_tools.md'
+    )
+
+    assert.ok(config)
+    assert.deepEqual(config.allowedBuiltinTools, [
+      'search_segments',
+      'get_segment_messages',
+      'get_segment_summaries',
+      'keyword_frequency',
+    ])
+  })
+})
diff --git a/packages/node-runtime/src/ai/assistant-parser.ts b/packages/node-runtime/src/ai/assistant-parser.ts
index 20b618e8..daf2517f 100644
--- a/packages/node-runtime/src/ai/assistant-parser.ts
+++ b/packages/node-runtime/src/ai/assistant-parser.ts
@@ -4,6 +4,7 @@
 
 import * as path from 'path'
 import matter from 'gray-matter'
+import { normalizeBuiltinToolNames } from '@openchatlab/core'
 import type { AssistantConfig } from './types'
 
 export function parseAssistantFile(content: string, filePath: string): AssistantConfig | null {
@@ -19,7 +20,7 @@ export function parseAssistantFile(content: string, filePath: string): Assistant
       name,
       systemPrompt: body.trim(),
       presetQuestions: parseStringArray(fm.presetQuestions),
-      allowedBuiltinTools: parseStringArray(fm.allowedBuiltinTools),
+      allowedBuiltinTools: normalizeBuiltinToolNames(parseStringArray(fm.allowedBuiltinTools)),
       builtinId: typeof fm.builtinId === 'string' ? fm.builtinId : undefined,
       applicableChatTypes: parseChatTypes(fm.applicableChatTypes),
       supportedLocales: parseStringArray(fm.supportedLocales),
@@ -38,7 +39,7 @@ export function serializeAssistant(config: AssistantConfig): string {
   if (config.builtinId) fm.builtinId = config.builtinId
   if (config.applicableChatTypes?.length) fm.applicableChatTypes = config.applicableChatTypes
   if (config.supportedLocales?.length) fm.supportedLocales = config.supportedLocales
-  if (config.allowedBuiltinTools?.length) fm.allowedBuiltinTools = config.allowedBuiltinTools
+  if (config.allowedBuiltinTools?.length) fm.allowedBuiltinTools = normalizeBuiltinToolNames(config.allowedBuiltinTools)
   if (config.presetQuestions?.length) fm.presetQuestions = config.presetQuestions
 
   return matter.stringify(`\n${config.systemPrompt}\n`, fm)
diff --git a/packages/node-runtime/src/database-manager.test.ts b/packages/node-runtime/src/database-manager.test.ts
index d8e97db3..7f093076 100644
--- a/packages/node-runtime/src/database-manager.test.ts
+++ b/packages/node-runtime/src/database-manager.test.ts
@@ -131,7 +131,7 @@ test('open backfills FTS index when migrating legacy sessions', () => {
   assert.ok(db)
 
   const version = db.prepare('SELECT schema_version FROM meta LIMIT 1').get() as { schema_version: number }
-  assert.equal(version.schema_version, 5)
+  assert.equal(version.schema_version, CURRENT_SCHEMA_VERSION)
 
   const ftsCount = db.prepare('SELECT COUNT(*) as total FROM message_fts').get() as { total: number }
   assert.equal(ftsCount.total, 1)
@@ -144,6 +144,163 @@ test('open backfills FTS index when migrating legacy sessions', () => {
   manager.closeAll()
 })
 
+test('open migrates v2 chat_session schema to current segment schema', () => {
+  const root = makeTempDir()
+  const dbDir = path.join(root, 'data', 'databases')
+  fs.mkdirSync(dbDir, { recursive: true })
+  const dbPath = path.join(dbDir, 'v2-segment-schema.db')
+
+  const rawDb = new Database(dbPath, { nativeBinding })
+  rawDb.exec(`
+    CREATE TABLE meta (
+      name TEXT NOT NULL,
+      platform TEXT NOT NULL,
+      type TEXT NOT NULL,
+      imported_at INTEGER NOT NULL,
+      schema_version INTEGER DEFAULT 2
+    );
+    INSERT INTO meta (name, platform, type, imported_at, schema_version)
+    VALUES ('V2 Segment Schema', 'qq', 'group', 1000, 2);
+
+    CREATE TABLE member (
+      id INTEGER PRIMARY KEY AUTOINCREMENT,
+      platform_id TEXT NOT NULL UNIQUE,
+      account_name TEXT
+    );
+    INSERT INTO member (platform_id, account_name) VALUES ('u1', 'Alice');
+
+    CREATE TABLE message (
+      id INTEGER PRIMARY KEY AUTOINCREMENT,
+      sender_id INTEGER NOT NULL,
+      ts INTEGER NOT NULL,
+      type INTEGER NOT NULL,
+      content TEXT,
+      platform_message_id TEXT DEFAULT NULL
+    );
+    INSERT INTO message (sender_id, ts, type, content) VALUES (1, 1000, 0, 'hello v2');
+  `)
+  rawDb.close()
+
+  const manager = new DatabaseManager(createPathProvider(root), { nativeBinding })
+  const db = manager.open('v2-segment-schema')
+  assert.ok(db)
+
+  const version = db.prepare('SELECT schema_version FROM meta LIMIT 1').get() as { schema_version: number }
+  assert.equal(version.schema_version, CURRENT_SCHEMA_VERSION)
+
+  const segmentTable = db.prepare("SELECT 1 FROM sqlite_master WHERE type = 'table' AND name = 'segment'").get()
+  const legacyTable = db.prepare("SELECT 1 FROM sqlite_master WHERE type = 'table' AND name = 'chat_session'").get()
+  assert.ok(segmentTable)
+  assert.equal(legacyTable, undefined)
+
+  const contextColumns = db.pragma('table_info(message_context)') as Array<{ name: string }>
+  assert.equal(
+    contextColumns.some((col) => col.name === 'segment_id'),
+    true
+  )
+  assert.equal(
+    contextColumns.some((col) => col.name === 'session_id'),
+    false
+  )
+
+  manager.closeAll()
+})
+
+test('open migrates legacy chat_session rows into segment after v5 creates segment table', () => {
+  const root = makeTempDir()
+  const dbDir = path.join(root, 'data', 'databases')
+  fs.mkdirSync(dbDir, { recursive: true })
+  const dbPath = path.join(dbDir, 'legacy-segments.db')
+
+  const rawDb = new Database(dbPath, { nativeBinding })
+  rawDb.exec(`
+    CREATE TABLE meta (
+      name TEXT NOT NULL,
+      platform TEXT NOT NULL,
+      type TEXT NOT NULL,
+      imported_at INTEGER NOT NULL,
+      schema_version INTEGER DEFAULT 4
+    );
+    INSERT INTO meta (name, platform, type, imported_at, schema_version)
+    VALUES ('Legacy Segment Chat', 'qq', 'group', 1000, 4);
+
+    CREATE TABLE member (
+      id INTEGER PRIMARY KEY AUTOINCREMENT,
+      platform_id TEXT NOT NULL UNIQUE,
+      account_name TEXT
+    );
+    INSERT INTO member (platform_id, account_name) VALUES ('u1', 'Alice');
+
+    CREATE TABLE message (
+      id INTEGER PRIMARY KEY AUTOINCREMENT,
+      sender_id INTEGER NOT NULL,
+      ts INTEGER NOT NULL,
+      type INTEGER NOT NULL,
+      content TEXT
+    );
+    INSERT INTO message (sender_id, ts, type, content) VALUES (1, 1000, 0, 'hello segment');
+
+    CREATE TABLE chat_session (
+      id INTEGER PRIMARY KEY AUTOINCREMENT,
+      start_ts INTEGER NOT NULL,
+      end_ts INTEGER NOT NULL,
+      message_count INTEGER DEFAULT 0,
+      is_manual INTEGER DEFAULT 0,
+      summary TEXT
+    );
+    INSERT INTO chat_session (id, start_ts, end_ts, message_count, is_manual, summary)
+    VALUES (7, 1000, 1010, 1, 0, 'legacy summary');
+
+    CREATE TABLE message_context (
+      message_id INTEGER PRIMARY KEY,
+      session_id INTEGER NOT NULL,
+      topic_id INTEGER
+    );
+    INSERT INTO message_context (message_id, session_id, topic_id) VALUES (1, 7, 3);
+  `)
+  rawDb.close()
+
+  const manager = new DatabaseManager(createPathProvider(root), { nativeBinding })
+  const db = manager.open('legacy-segments')
+  assert.ok(db)
+
+  const version = db.prepare('SELECT schema_version FROM meta LIMIT 1').get() as { schema_version: number }
+  assert.equal(version.schema_version, CURRENT_SCHEMA_VERSION)
+
+  const legacyTable = db.prepare("SELECT 1 FROM sqlite_master WHERE type = 'table' AND name = 'chat_session'").get()
+  assert.equal(legacyTable, undefined)
+
+  const segment = db.prepare('SELECT id, start_ts, end_ts, message_count, summary FROM segment').get() as
+    | { id: number; start_ts: number; end_ts: number; message_count: number; summary: string | null }
+    | undefined
+  assert.deepEqual(segment, {
+    id: 7,
+    start_ts: 1000,
+    end_ts: 1010,
+    message_count: 1,
+    summary: 'legacy summary',
+  })
+
+  const contextColumns = db.pragma('table_info(message_context)') as Array<{ name: string }>
+  assert.equal(
+    contextColumns.some((col) => col.name === 'segment_id'),
+    true
+  )
+  assert.equal(
+    contextColumns.some((col) => col.name === 'session_id'),
+    false
+  )
+
+  const context = db.prepare('SELECT message_id, segment_id, topic_id FROM message_context').get() as {
+    message_id: number
+    segment_id: number
+    topic_id: number
+  }
+  assert.deepEqual(context, { message_id: 1, segment_id: 7, topic_id: 3 })
+
+  manager.closeAll()
+})
+
 test('open preserves readonly access for current-schema databases', { skip: process.platform === 'win32' }, () => {
   const root = makeTempDir()
   const dbDir = path.join(root, 'data', 'databases')
diff --git a/packages/node-runtime/src/migrations/chat-db-migrations.ts b/packages/node-runtime/src/migrations/chat-db-migrations.ts
index 51d4ccbd..3359a9bb 100644
--- a/packages/node-runtime/src/migrations/chat-db-migrations.ts
+++ b/packages/node-runtime/src/migrations/chat-db-migrations.ts
@@ -71,10 +71,10 @@ export function getChatDbMigrations(deps?: MigrationDeps): CoreMigration[] {
     },
     {
       version: 3,
-      description: 'Add segment and message_context tables',
+      description: 'Add chat_session and message_context tables',
       up: (db: DatabaseAdapter) => {
         db.exec(`
-          CREATE TABLE IF NOT EXISTS segment (
+          CREATE TABLE IF NOT EXISTS chat_session (
             id INTEGER PRIMARY KEY AUTOINCREMENT,
             start_ts INTEGER NOT NULL,
             end_ts INTEGER NOT NULL,
@@ -85,7 +85,7 @@ export function getChatDbMigrations(deps?: MigrationDeps): CoreMigration[] {
         `)
 
         try {
-          db.exec('CREATE INDEX IF NOT EXISTS idx_segment_time ON segment(start_ts, end_ts)')
+          db.exec('CREATE INDEX IF NOT EXISTS idx_session_time ON chat_session(start_ts, end_ts)')
         } catch {
           // Index may already exist
         }
@@ -93,13 +93,13 @@ export function getChatDbMigrations(deps?: MigrationDeps): CoreMigration[] {
         db.exec(`
           CREATE TABLE IF NOT EXISTS message_context (
             message_id INTEGER PRIMARY KEY,
-            segment_id INTEGER NOT NULL,
+            session_id INTEGER NOT NULL,
             topic_id INTEGER
           )
         `)
 
         try {
-          db.exec('CREATE INDEX IF NOT EXISTS idx_context_segment ON message_context(segment_id)')
+          db.exec('CREATE INDEX IF NOT EXISTS idx_context_session ON message_context(session_id)')
         } catch {
           // Index may already exist
         }
@@ -202,7 +202,7 @@ export function getChatDbMigrations(deps?: MigrationDeps): CoreMigration[] {
         addColumnIfMissing(db, 'message', 'platform_message_id', 'TEXT DEFAULT NULL')
 
         db.exec(`
-          CREATE TABLE IF NOT EXISTS segment (
+          CREATE TABLE IF NOT EXISTS chat_session (
             id INTEGER PRIMARY KEY AUTOINCREMENT,
             start_ts INTEGER NOT NULL,
             end_ts INTEGER NOT NULL,
@@ -214,15 +214,15 @@ export function getChatDbMigrations(deps?: MigrationDeps): CoreMigration[] {
         db.exec(`
           CREATE TABLE IF NOT EXISTS message_context (
             message_id INTEGER PRIMARY KEY,
-            segment_id INTEGER NOT NULL,
+            session_id INTEGER NOT NULL,
             topic_id INTEGER
           )
         `)
 
         db.exec('CREATE INDEX IF NOT EXISTS idx_message_platform_id ON message(platform_message_id)')
         db.exec('CREATE INDEX IF NOT EXISTS idx_member_name_history_member_id ON member_name_history(member_id)')
-        db.exec('CREATE INDEX IF NOT EXISTS idx_segment_time ON segment(start_ts, end_ts)')
-        db.exec('CREATE INDEX IF NOT EXISTS idx_context_segment ON message_context(segment_id)')
+        db.exec('CREATE INDEX IF NOT EXISTS idx_session_time ON chat_session(start_ts, end_ts)')
+        db.exec('CREATE INDEX IF NOT EXISTS idx_context_session ON message_context(session_id)')
       },
     },
     {
@@ -241,8 +241,18 @@ export function getChatDbMigrations(deps?: MigrationDeps): CoreMigration[] {
           DROP INDEX IF EXISTS idx_context_session;
         `)
 
-        if (hasTable('chat_session') && !hasTable('segment')) {
+        const hasLegacyChatSession = hasTable('chat_session')
+        const hasSegment = hasTable('segment')
+
+        if (hasLegacyChatSession && !hasSegment) {
           db.exec('ALTER TABLE chat_session RENAME TO segment')
+        } else if (hasLegacyChatSession && hasSegment) {
+          db.exec(`
+            INSERT OR IGNORE INTO segment (id, start_ts, end_ts, message_count, is_manual, summary)
+            SELECT id, start_ts, end_ts, message_count, is_manual, summary
+            FROM chat_session;
+            DROP TABLE chat_session;
+          `)
         }
 
         if (hasTable('message_context') && hasColumn(db, 'message_context', 'session_id')) {