diff --git a/cli/src/hooks/helpers/__tests__/send-message.test.ts b/cli/src/hooks/helpers/__tests__/send-message.test.ts
index 7e23893249..8899c19b6f 100644
--- a/cli/src/hooks/helpers/__tests__/send-message.test.ts
+++ b/cli/src/hooks/helpers/__tests__/send-message.test.ts
@@ -37,6 +37,7 @@ const {
   finalizeQueueState,
   resetEarlyReturnState,
 } = await import('../send-message')
+const { createRunConfig } = await import('../../../utils/create-run-config')
 const { createBatchedMessageUpdater } =
   await import('../../../utils/message-updater')
 import { createPaymentRequiredError } from '@codebuff/sdk'
@@ -1858,4 +1859,144 @@ describe('freebuff gate errors', () => {
     // (which would set a userError from the message).
     expect(messages[0].userError).toBeUndefined()
   })
+
+  describe('session state preservation on user abort and error / session expiration', () => {
+    test('user abort (Esc): follow-up message inherits active snapshot with message history and tool calls', () => {
+      const previousRunStateRef = { current: null as RunState | null }
+      let committedStoreRunState: RunState | null = null
+      let currentChatDir = '/chat-1'
+
+      const syncRunState = (state: RunState) => {
+        if (currentChatDir !== '/chat-1') return
+        previousRunStateRef.current = state
+        committedStoreRunState = state
+      }
+
+      const activeSnapshot: RunState = {
+        sessionState: {
+          fileContext: { projectRoot: '/project', files: {} } as any,
+          mainAgentState: {
+            agentId: 'agent-1',
+            agentType: 'base2',
+            messageHistory: [
+              { role: 'user', content: [{ type: 'text', text: 'implement authentication' }] },
+              { role: 'assistant', content: [{ type: 'text', text: 'reading project files' }] },
+              {
+                role: 'tool',
+                toolName: 'read_files',
+                content: [{ type: 'text', value: { files: ['src/auth.ts'] } }],
+              } as any,
+            ],
+          } as any,
+        },
+        traceSessionId: 'trace-1',
+      }
+
+      // User hits Esc mid-stream: registerActiveRun abort callback fires
+      syncRunState(activeSnapshot)
+
+      // User immediately sends follow-up prompt
+      const runConfigB = createRunConfig({
+        logger: { debug: () => {}, warn: () => {}, error: () => {}, info: () => {} } as any,
+        agent: 'base2',
+        prompt: 'also verify tests',
+        content: undefined,
+        previousRunState: previousRunStateRef.current,
+        agentDefinitions: [],
+        eventHandlerState: {} as any,
+      })
+
+      // Verify that previousRun carries full history rather than empty []
+      expect(runConfigB.previousRun).toBe(activeSnapshot)
+      expect(runConfigB.previousRun?.sessionState?.mainAgentState.messageHistory).toHaveLength(3)
+      expect(
+        runConfigB.previousRun?.sessionState?.mainAgentState.messageHistory[0].content[0].text,
+      ).toBe('implement authentication')
+      expect(
+        runConfigB.previousRun?.sessionState?.mainAgentState.messageHistory[2].toolName,
+      ).toBe('read_files')
+      expect(committedStoreRunState).toBe(activeSnapshot)
+    })
+
+    test('session expiration / error: sending "continue" inherits expired session snapshot', () => {
+      const previousRunStateRef = { current: null as RunState | null }
+      let committedStoreRunState: RunState | null = null
+      let currentChatDir = '/chat-1'
+
+      const syncRunState = (state: RunState) => {
+        if (currentChatDir !== '/chat-1') return
+        previousRunStateRef.current = state
+        committedStoreRunState = state
+      }
+
+      const errorSnapshot: RunState = {
+        sessionState: {
+          fileContext: { projectRoot: '/project', files: {} } as any,
+          mainAgentState: {
+            agentId: 'agent-1',
+            agentType: 'base2',
+            messageHistory: [
+              { role: 'user', content: [{ type: 'text', text: 'turn 1 prompt' }] },
+              { role: 'assistant', content: [{ type: 'text', text: 'turn 1 response' }] },
+              { role: 'user', content: [{ type: 'text', text: 'turn 2 prompt' }] },
+            ],
+          } as any,
+        },
+        traceSessionId: 'trace-2',
+        output: {
+          type: 'error',
+          message: 'Your free session ended',
+          error: 'session_expired',
+        } as any,
+      }
+
+      // Session expiration error caught in useSendMessage catch block
+      syncRunState(errorSnapshot)
+
+      // User sends "continue" after session ended banner
+      const runConfigB = createRunConfig({
+        logger: { debug: () => {}, warn: () => {}, error: () => {}, info: () => {} } as any,
+        agent: 'base2',
+        prompt: 'continue',
+        content: undefined,
+        previousRunState: previousRunStateRef.current,
+        agentDefinitions: [],
+        eventHandlerState: {} as any,
+      })
+
+      expect(runConfigB.previousRun).toBe(errorSnapshot)
+      expect(runConfigB.previousRun?.sessionState?.mainAgentState.messageHistory).toHaveLength(3)
+      expect(
+        runConfigB.previousRun?.sessionState?.mainAgentState.messageHistory[2].content[0].text,
+      ).toBe('turn 2 prompt')
+      expect(committedStoreRunState).toBe(errorSnapshot)
+    })
+
+    test('chat switch isolation: syncRunState is a no-op when active chat directory has changed', () => {
+      const previousRunStateRef = { current: null as RunState | null }
+      let committedStoreRunState: RunState | null = null
+      let currentChatDir = '/chat-2' // User switched to chat 2
+
+      const syncRunState = (state: RunState) => {
+        if (currentChatDir !== '/chat-1') return // Stale run from chat 1
+        previousRunStateRef.current = state
+        committedStoreRunState = state
+      }
+
+      const staleSnapshot: RunState = {
+        sessionState: {
+          mainAgentState: {
+            messageHistory: [{ role: 'user', content: [{ type: 'text', text: 'chat 1 prompt' }] }],
+          } as any,
+        } as any,
+        traceSessionId: 'trace-stale',
+      }
+
+      syncRunState(staleSnapshot)
+
+      // Must NOT leak state into chat 2
+      expect(previousRunStateRef.current).toBeNull()
+      expect(committedStoreRunState).toBeNull()
+    })
+  })
 })
diff --git a/cli/src/hooks/helpers/send-message.ts b/cli/src/hooks/helpers/send-message.ts
index f5432dbc97..8602fc8fa8 100644
--- a/cli/src/hooks/helpers/send-message.ts
+++ b/cli/src/hooks/helpers/send-message.ts
@@ -305,11 +305,8 @@ export const setupStreamingContext = (params: {
   abortController.signal.addEventListener('abort', () => {
     // Abort means the user stopped streaming; update UI with an interruption notice.
     // Release the chain lock immediately so new messages can be sent directly instead
-    // of being queued. The minor trade-off is that if the user sends a new message
-    // before client.run() resolves, it may use stale previousRunStateRef. This is
-    // acceptable because: (1) the user explicitly cancelled, and (2) client.run()
-    // will update previousRunStateRef when it eventually resolves, so subsequent
-    // runs will have the full state.
+    // of being queued. registerActiveRun updates previousRunStateRef synchronously
+    // with the latest snapshot so immediate follow-ups retain preserved context.
     streamRefs.setters.setWasAbortedByUser(true)
     setIsRetrying(false)
     timerController.stop('aborted')
diff --git a/cli/src/hooks/use-send-message.ts b/cli/src/hooks/use-send-message.ts
index 39065317ee..7433f0fd89 100644
--- a/cli/src/hooks/use-send-message.ts
+++ b/cli/src/hooks/use-send-message.ts
@@ -315,6 +315,12 @@ export const useSendMessage = ({
         clearActiveRun(runOwnerId)
       }
 
+      const syncRunState = (state: RunState) => {
+        if (!runChatIsCurrent()) return
+        previousRunStateRef.current = state
+        setRunState(state)
+      }
+
       registerActiveRun(runOwnerId, (reason) => {
         if (abortController.signal.aborted) return
 
@@ -330,6 +336,10 @@ export const useSendMessage = ({
           if (isProcessingQueueRef) isProcessingQueueRef.current = false
         }
 
+        // Keep in-memory previousRunStateRef fresh so immediate follow-up
+        // messages carry the latest snapshot even before client.run settles.
+        syncRunState(latestRunStateSnapshot)
+
         // Capture the old chat's array now. Context-changing callers reset the
         // store immediately after stopActiveRun returns.
         scheduleCheckpointSave(
@@ -644,8 +654,7 @@ export const useSendMessage = ({
         // same chat, so the interrupted turn is still saved as before.)
         if (runChatIsCurrent()) {
           // Finalize: persist state and mark complete
-          previousRunStateRef.current = runState
-          setRunState(runState)
+          syncRunState(runState)
           setIsRetrying(false)
 
           // Drop any queued/in-flight async checkpoint first so a stale write
@@ -697,6 +706,7 @@ export const useSendMessage = ({
           // first so a stale write can't clobber this one. Skipped after a
           // mid-run chat switch — the store's messages belong to the new chat.
           if (runChatIsCurrent()) {
+            syncRunState(latestRunStateSnapshot)
             await settleCheckpointSave()
             saveChatState(
               latestRunStateSnapshot,