diff --git a/src/renderer/src/components/sidebar/LinearAgentSkillSetupPrompt.test.tsx b/src/renderer/src/components/sidebar/LinearAgentSkillSetupPrompt.test.tsx
index cef69177f0f..9ed0ccf3263 100644
--- a/src/renderer/src/components/sidebar/LinearAgentSkillSetupPrompt.test.tsx
+++ b/src/renderer/src/components/sidebar/LinearAgentSkillSetupPrompt.test.tsx
@@ -682,6 +682,45 @@ describe('LinearAgentSkillSetupPrompt', () => {
     expect(document.body.textContent).not.toContain('Linear ticket access is ready')
   })
 
+  it('accepts same-context prerequisite CLI status callbacks after a newer Re-check', async () => {
+    let reportHostCliStatus: ((status: CliInstallStatus) => void) | null = null
+    let resolveEnsureCli: () => void = () => {}
+    mocks.ensureCli.mockImplementationOnce(
+      async (options?: { onStatusChange?: (status: CliInstallStatus) => void }) => {
+        reportHostCliStatus = options?.onStatusChange ?? null
+        await new Promise<void>((resolve) => {
+          resolveEnsureCli = resolve
+        })
+        return null
+      }
+    )
+    await renderPrompt({ linked: true, remote: false, surface: 'modal' })
+
+    await act(async () => {
+      findBodyButton('Mock install')?.dispatchEvent(new MouseEvent('click', { bubbles: true }))
+    })
+
+    mocks.getCliStatus.mockResolvedValue(
+      cliStatus({ state: 'not_installed', pathConfigured: false })
+    )
+    await act(async () => {
+      findBodyButton('Re-check')?.dispatchEvent(new MouseEvent('click', { bubbles: true }))
+    })
+    await settleRender()
+
+    await act(async () => {
+      reportHostCliStatus?.(cliStatus({}))
+      resolveEnsureCli()
+    })
+    await settleRender()
+
+    expect(document.body.textContent).toContain(
+      'Enable agents to read and edit the attached Linear ticket.'
+    )
+    expect(document.body.textContent).toContain('Linear agent skill is missing.')
+    expect(document.body.textContent).not.toContain('Orca CLI is missing.')
+  })
+
   it('ignores older same-context CLI refreshes that finish after a newer Re-check', async () => {
     const rendered = await renderPrompt({ linked: true, remote: false })
     const recheckButton = Array.from(rendered.querySelectorAll('button')).find(
diff --git a/src/renderer/src/components/sidebar/LinearAgentSkillSetupPrompt.tsx b/src/renderer/src/components/sidebar/LinearAgentSkillSetupPrompt.tsx
index 8884ad87c8c..a330acb4587 100644
--- a/src/renderer/src/components/sidebar/LinearAgentSkillSetupPrompt.tsx
+++ b/src/renderer/src/components/sidebar/LinearAgentSkillSetupPrompt.tsx
@@ -134,6 +134,12 @@ export function LinearAgentSkillSetupPrompt({
     []
   )
 
+  const writeCliStatusForIdentity = useCallback((requestIdentity: string, write: () => void) => {
+    if (currentSetupCheckIdentityRef.current === requestIdentity) {
+      write()
+    }
+  }, [])
+
   const refreshCliStatus = useCallback(async (): Promise<void> => {
     const requestIdentity = setupCheckIdentity
     const requestGeneration = ++cliRefreshGenerationRef.current
@@ -280,9 +286,8 @@ export function LinearAgentSkillSetupPrompt({
       }
       onBeforeOpenTerminal={async () => {
         const requestIdentity = setupCheckIdentity
-        const requestGeneration = ++cliRefreshGenerationRef.current
         const writeIfCurrent = (write: () => void): void => {
-          writeCliStatusIfCurrent(requestIdentity, requestGeneration, write)
+          writeCliStatusForIdentity(requestIdentity, write)
         }
         const nextStatus =
           agentRuntime.runtime === 'wsl'