diff --git a/src/features/tmux-subagent/manager.test.ts b/src/features/tmux-subagent/manager.test.ts
index 84c7bc441..e63f4bf4d 100644
--- a/src/features/tmux-subagent/manager.test.ts
+++ b/src/features/tmux-subagent/manager.test.ts
@@ -1932,6 +1932,47 @@ describe('TmuxSessionManager', () => {
       expect(mockKillTmuxSessionIfExists).toHaveBeenCalledTimes(0)
     })
 
+    test('#given sweepStaleOmoAgentSessions throws on first onSessionCreated #when second onSessionCreated fires #then sweep is retried instead of skipped forever', async () => {
+      // given
+      mockSweepStaleOmoAgentSessions.mockClear()
+      mockSweepStaleOmoAgentSessions.mockImplementationOnce(async () => {
+        throw new Error('simulated sweep failure')
+      })
+      mockIsInsideTmux.mockReturnValue(true)
+      const { TmuxSessionManager } = await import('./manager')
+      const manager = new TmuxSessionManager(createMockContext(), createTmuxConfig({
+        enabled: true,
+        isolation: 'session',
+      }), mockTmuxDeps)
+
+      // when
+      await manager.onSessionCreated(createSessionCreatedEvent('ses_first', 'ses_parent', 'First'))
+      await manager.onSessionCreated(createSessionCreatedEvent('ses_second', 'ses_parent', 'Second'))
+
+      // then
+      expect(mockSweepStaleOmoAgentSessions).toHaveBeenCalledTimes(2)
+    })
+
+    test('#given sweepStaleOmoAgentSessions succeeds #when additional onSessionCreated events fire in same process #then sweep runs exactly once', async () => {
+      // given
+      mockSweepStaleOmoAgentSessions.mockClear()
+      mockSweepStaleOmoAgentSessions.mockImplementation(async () => 0)
+      mockIsInsideTmux.mockReturnValue(true)
+      const { TmuxSessionManager } = await import('./manager')
+      const manager = new TmuxSessionManager(createMockContext(), createTmuxConfig({
+        enabled: true,
+        isolation: 'session',
+      }), mockTmuxDeps)
+
+      // when
+      await manager.onSessionCreated(createSessionCreatedEvent('ses_a', 'ses_parent', 'A'))
+      await manager.onSessionCreated(createSessionCreatedEvent('ses_b', 'ses_parent', 'B'))
+      await manager.onSessionCreated(createSessionCreatedEvent('ses_c', 'ses_parent', 'C'))
+
+      // then
+      expect(mockSweepStaleOmoAgentSessions).toHaveBeenCalledTimes(1)
+    })
+
     test('#given killTmuxSessionIfExists throws #when cleanup runs #then cleanup still completes without throwing', async () => {
       // given
       mockKillTmuxSessionIfExists.mockClear()
diff --git a/src/features/tmux-subagent/manager.ts b/src/features/tmux-subagent/manager.ts
index 5734ff822..3340fb55d 100644
--- a/src/features/tmux-subagent/manager.ts
+++ b/src/features/tmux-subagent/manager.ts
@@ -67,6 +67,7 @@ export class TmuxSessionManager {
   private isolatedWindowPaneId: string | undefined
   private isolatedContainerNullStateCount = 0
   private staleSweepCompleted = false
+  private staleSweepInProgress = false
   constructor(ctx: PluginInput, tmuxConfig: TmuxConfig, deps: TmuxUtilDeps = defaultTmuxDeps) {
     this.client = ctx.client
     this.tmuxConfig = tmuxConfig
@@ -977,27 +978,32 @@ export class TmuxSessionManager {
     }
 
     this.staleSweepCompleted = false
+    this.staleSweepInProgress = false
 
     log("[tmux-session-manager] cleanup complete")
   }
 
   private async sweepStaleIsolatedSessionsOnce(): Promise<void> {
     if (this.staleSweepCompleted) return
+    if (this.staleSweepInProgress) return
     if (this.tmuxConfig.isolation !== "session") {
       this.staleSweepCompleted = true
       return
     }
 
-    this.staleSweepCompleted = true
+    this.staleSweepInProgress = true
     try {
       const killed = await sweepStaleOmoAgentSessions()
       if (killed > 0) {
         log("[tmux-session-manager] stale isolated sessions swept", { killed })
       }
+      this.staleSweepCompleted = true
     } catch (error) {
       log("[tmux-session-manager] stale sweep failed", {
         error: String(error),
       })
+    } finally {
+      this.staleSweepInProgress = false
     }
   }
 }