diff --git a/scripts/system-check.test.ts b/scripts/system-check.test.ts
index 6937414c..7290ba63 100644
--- a/scripts/system-check.test.ts
+++ b/scripts/system-check.test.ts
@@ -20,6 +20,23 @@ describe('formatReachabilityFailureDetail', () => {
     )
   })
 
+  test('redacts credentials and sensitive query parameters in endpoint details', () => {
+    const detail = formatReachabilityFailureDetail(
+      'http://user:pass@localhost:11434/v1/models?token=abc123&mode=test',
+      502,
+      'bad gateway',
+      {
+        transport: 'chat_completions',
+        requestedModel: 'llama3.1:8b',
+        resolvedModel: 'llama3.1:8b',
+      },
+    )
+
+    expect(detail).toBe(
+      'Unexpected status 502 from http://redacted:redacted@localhost:11434/v1/models?token=redacted&mode=test. Body: bad gateway',
+    )
+  })
+
   test('adds alias/entitlement hint for codex model support 400s', () => {
     const detail = formatReachabilityFailureDetail(
       'https://chatgpt.com/backend-api/codex/responses',
diff --git a/scripts/system-check.ts b/scripts/system-check.ts
index 80e9ef26..8f87b59e 100644
--- a/scripts/system-check.ts
+++ b/scripts/system-check.ts
@@ -7,6 +7,11 @@ import {
   resolveProviderRequest,
   isLocalProviderUrl as isProviderLocalUrl,
 } from '../src/services/api/providerConfig.js'
+import {
+  getLocalOpenAICompatibleProviderLabel,
+  probeOllamaGenerationReadiness,
+} from '../src/utils/providerDiscovery.js'
+import { redactUrlForDisplay } from '../src/utils/urlRedaction.js'
 
 type CheckResult = {
   ok: boolean
@@ -69,7 +74,7 @@ export function formatReachabilityFailureDetail(
   },
 ): string {
   const compactBody = responseBody.trim().replace(/\s+/g, ' ').slice(0, 240)
-  const base = `Unexpected status ${status} from ${endpoint}.`
+  const base = `Unexpected status ${status} from ${redactUrlForDisplay(endpoint)}.`
   const bodySuffix = compactBody ? ` Body: ${compactBody}` : ''
 
   if (request.transport !== 'codex_responses' || status !== 400) {
@@ -255,7 +260,7 @@ function checkOpenAIEnv(): CheckResult[] {
     results.push(pass('OPENAI_MODEL', process.env.OPENAI_MODEL))
   }
 
-  results.push(pass('OPENAI_BASE_URL', request.baseUrl))
+  results.push(pass('OPENAI_BASE_URL', redactUrlForDisplay(request.baseUrl)))
 
   if (request.transport === 'codex_responses') {
     const credentials = resolveCodexApiCredentials(process.env)
@@ -308,7 +313,7 @@ async function checkBaseUrlReachability(): Promise<CheckResult> {
     return pass('Provider reachability', 'Skipped (OpenAI-compatible mode disabled).')
   }
 
-  if (useGithub) {
+  if (useGithub && !useOpenAI) {
     return pass(
       'Provider reachability',
       'Skipped for GitHub Models (inference endpoint differs from OpenAI /models probe).',
@@ -326,6 +331,7 @@ async function checkBaseUrlReachability(): Promise<CheckResult> {
   const endpoint = request.transport === 'codex_responses'
     ? `${request.baseUrl}/responses`
     : `${request.baseUrl}/models`
+  const redactedEndpoint = redactUrlForDisplay(endpoint)
 
   const controller = new AbortController()
   const timeout = setTimeout(() => controller.abort(), 4000)
@@ -375,7 +381,10 @@ async function checkBaseUrlReachability(): Promise<CheckResult> {
     })
 
     if (response.status === 200 || response.status === 401 || response.status === 403) {
-      return pass('Provider reachability', `Reached ${endpoint} (status ${response.status}).`)
+      return pass(
+        'Provider reachability',
+        `Reached ${redactedEndpoint} (status ${response.status}).`,
+      )
     }
 
     const responseBody = await response.text().catch(() => '')
@@ -391,12 +400,100 @@ async function checkBaseUrlReachability(): Promise<CheckResult> {
     )
   } catch (error) {
     const message = error instanceof Error ? error.message : String(error)
-    return fail('Provider reachability', `Failed to reach ${endpoint}: ${message}`)
+    return fail(
+      'Provider reachability',
+      `Failed to reach ${redactedEndpoint}: ${message}`,
+    )
   } finally {
     clearTimeout(timeout)
   }
 }
 
+async function checkProviderGenerationReadiness(): Promise<CheckResult> {
+  const useGemini = isTruthy(process.env.CLAUDE_CODE_USE_GEMINI)
+  const useOpenAI = isTruthy(process.env.CLAUDE_CODE_USE_OPENAI)
+  const useGithub = isTruthy(process.env.CLAUDE_CODE_USE_GITHUB)
+  const useMistral = isTruthy(process.env.CLAUDE_CODE_USE_MISTRAL)
+
+  if (!useGemini && !useOpenAI && !useGithub && !useMistral) {
+    return pass('Provider generation readiness', 'Skipped (OpenAI-compatible mode disabled).')
+  }
+
+  if (useGithub && !useOpenAI) {
+    return pass(
+      'Provider generation readiness',
+      'Skipped for GitHub Models (runtime generation uses a different endpoint flow).',
+    )
+  }
+
+  if (useGemini || useMistral) {
+    return pass(
+      'Provider generation readiness',
+      'Skipped for managed provider mode.',
+    )
+  }
+
+  if (!useOpenAI) {
+    return pass('Provider generation readiness', 'Skipped (OpenAI-compatible mode disabled).')
+  }
+
+  const request = resolveProviderRequest({
+    model: process.env.OPENAI_MODEL,
+    baseUrl: process.env.OPENAI_BASE_URL,
+  })
+
+  if (request.transport === 'codex_responses') {
+    return pass(
+      'Provider generation readiness',
+      'Skipped for Codex responses (reachability probe already performs a lightweight generation request).',
+    )
+  }
+
+  if (!isLocalBaseUrl(request.baseUrl)) {
+    return pass('Provider generation readiness', 'Skipped for non-local provider URL.')
+  }
+
+  const localProviderLabel = getLocalOpenAICompatibleProviderLabel(request.baseUrl)
+  if (localProviderLabel !== 'Ollama') {
+    return pass(
+      'Provider generation readiness',
+      `Skipped for ${localProviderLabel} (no provider-specific generation probe).`,
+    )
+  }
+
+  const readiness = await probeOllamaGenerationReadiness({
+    baseUrl: request.baseUrl,
+    model: request.requestedModel,
+  })
+
+  if (readiness.state === 'ready') {
+    return pass(
+      'Provider generation readiness',
+      `Generated a test response with ${readiness.probeModel ?? request.requestedModel}.`,
+    )
+  }
+
+  if (readiness.state === 'unreachable') {
+    return fail(
+      'Provider generation readiness',
+      `Could not reach Ollama at ${redactUrlForDisplay(request.baseUrl)}.`,
+    )
+  }
+
+  if (readiness.state === 'no_models') {
+    return fail(
+      'Provider generation readiness',
+      'Ollama is reachable, but no installed models were found. Pull a model first (for example: ollama pull qwen2.5-coder:7b).',
+    )
+  }
+
+  const detailSuffix = readiness.detail ? ` Detail: ${readiness.detail}.` : ''
+  return fail(
+    'Provider generation readiness',
+    `Ollama is reachable, but generation failed for ${readiness.probeModel ?? request.requestedModel}.${detailSuffix}`,
+  )
+}
+
 function isAtomicChatUrl(baseUrl: string): boolean {
   try {
     const parsed = new URL(baseUrl)
@@ -567,6 +664,7 @@ async function main(): Promise<void> {
   results.push(checkBuildArtifacts())
   results.push(...checkOpenAIEnv())
   results.push(await checkBaseUrlReachability())
+  results.push(await checkProviderGenerationReadiness())
   results.push(checkOllamaProcessorMode())
 
   if (!options.json) {
diff --git a/src/commands/provider/provider.tsx b/src/commands/provider/provider.tsx
index 0b026f7e..6d954d2a 100644
--- a/src/commands/provider/provider.tsx
+++ b/src/commands/provider/provider.tsx
@@ -66,10 +66,44 @@ import {
 import {
   getOllamaChatBaseUrl,
   getLocalOpenAICompatibleProviderLabel,
-  hasLocalOllama,
-  listOllamaModels,
+  probeOllamaGenerationReadiness,
+  type OllamaGenerationReadiness,
 } from '../../utils/providerDiscovery.js'
 
+function describeOllamaReadinessIssue(
+  readiness: OllamaGenerationReadiness,
+  options?: {
+    baseUrl?: string
+    allowManualFallback?: boolean
+  },
+): string {
+  const endpoint = options?.baseUrl ?? 'http://localhost:11434'
+
+  if (readiness.state === 'unreachable') {
+    return `Could not reach Ollama at ${endpoint}. Start Ollama first, then run /provider again.`
+  }
+
+  if (readiness.state === 'no_models') {
+    const manualSuffix = options?.allowManualFallback
+      ? ', or enter details manually'
+      : ''
+    return `Ollama is running, but no installed models were found. Pull a chat model such as qwen2.5-coder:7b or llama3.1:8b first${manualSuffix}.`
+  }
+
+  if (readiness.state === 'generation_failed') {
+    const modelHint = readiness.probeModel ?? 'the selected model'
+    const detailSuffix = readiness.detail
+      ? ` Details: ${readiness.detail}.`
+      : ''
+    const manualSuffix = options?.allowManualFallback
+      ? ' You can also enter details manually.'
+      : ''
+    return `Ollama is reachable and models are installed, but a generation probe failed for ${modelHint}.${detailSuffix} Run "ollama run ${modelHint}" once and retry.${manualSuffix}`
+  }
+
+  return ''
+}
+
 type ProviderChoice = 'auto' | ProviderProfile | 'codex-oauth' | 'clear'
 
 type Step =
@@ -715,6 +749,7 @@ function AutoRecommendationStep({
     | {
         state: 'openai'
         defaultModel: string
+        reason: string
       }
     | {
         state: 'error'
@@ -728,19 +763,27 @@ function AutoRecommendationStep({
     void (async () => {
       const defaultModel = getGoalDefaultOpenAIModel(goal)
       try {
-        const ollamaAvailable = await hasLocalOllama()
-        if (!ollamaAvailable) {
+        const readiness = await probeOllamaGenerationReadiness()
+        if (readiness.state !== 'ready') {
           if (!cancelled) {
-            setStatus({ state: 'openai', defaultModel })
+            setStatus({
+              state: 'openai',
+              defaultModel,
+              reason: describeOllamaReadinessIssue(readiness),
+            })
           }
           return
         }
 
-        const models = await listOllamaModels()
-        const recommended = recommendOllamaModel(models, goal)
+        const recommended = recommendOllamaModel(readiness.models, goal)
         if (!recommended) {
           if (!cancelled) {
-            setStatus({ state: 'openai', defaultModel })
+            setStatus({
+              state: 'openai',
+              defaultModel,
+              reason:
+                'Ollama responded to a generation probe, but no recommended chat model matched this goal.',
+            })
           }
           return
         }
@@ -796,10 +839,10 @@ function AutoRecommendationStep({
       <Dialog title="Auto setup fallback" onCancel={onCancel}>
         <Box flexDirection="column" gap={1}>
           <Text>
-            No viable local Ollama chat model was detected. Auto setup can
-            continue into OpenAI-compatible setup with a default model of{' '}
+            Auto setup can continue into OpenAI-compatible setup with a default model of{' '}
             {status.defaultModel}.
           </Text>
+          <Text dimColor>{status.reason}</Text>
           <Select
             options={[
               { label: 'Continue to OpenAI-compatible setup', value: 'continue' },
@@ -883,32 +926,19 @@ function OllamaModelStep({
     let cancelled = false
 
     void (async () => {
-      const available = await hasLocalOllama()
-      if (!available) {
+      const readiness = await probeOllamaGenerationReadiness()
+      if (readiness.state !== 'ready') {
         if (!cancelled) {
           setStatus({
             state: 'unavailable',
-            message:
-              'Could not reach Ollama at http://localhost:11434. Start Ollama first, then run /provider again.',
+            message: describeOllamaReadinessIssue(readiness),
           })
         }
         return
       }
 
-      const models = await listOllamaModels()
-      if (models.length === 0) {
-        if (!cancelled) {
-          setStatus({
-            state: 'unavailable',
-            message:
-              'Ollama is running, but no installed models were found. Pull a chat model such as qwen2.5-coder:7b or llama3.1:8b first.',
-          })
-        }
-        return
-      }
-
-      const ranked = rankOllamaModels(models, 'balanced')
-      const recommended = recommendOllamaModel(models, 'balanced')
+      const ranked = rankOllamaModels(readiness.models, 'balanced')
+      const recommended = recommendOllamaModel(readiness.models, 'balanced')
       if (!cancelled) {
         setStatus({
           state: 'ready',
diff --git a/src/components/ProviderManager.test.tsx b/src/components/ProviderManager.test.tsx
index 79dc5110..15833ffa 100644
--- a/src/components/ProviderManager.test.tsx
+++ b/src/components/ProviderManager.test.tsx
@@ -149,17 +149,21 @@ function mockProviderManagerDependencies(
     applySavedProfileToCurrentSession?: (...args: unknown[]) => Promise<string | null>
     clearCodexCredentials?: () => { success: boolean; warning?: string }
     getProviderProfiles?: () => unknown[]
-    hasLocalOllama?: () => Promise<boolean>
-    listOllamaModels?: () => Promise<
-      Array<{
-        name: string
-        sizeBytes?: number | null
-        family?: string | null
-        families?: string[]
-        parameterSize?: string | null
-        quantizationLevel?: string | null
-      }>
-    >
+    probeOllamaGenerationReadiness?: () => Promise<{
+      state: 'ready' | 'unreachable' | 'no_models' | 'generation_failed'
+      models: Array<
+        {
+          name: string
+          sizeBytes?: number | null
+          family?: string | null
+          families?: string[]
+          parameterSize?: string | null
+          quantizationLevel?: string | null
+        }
+      >
+      probeModel?: string
+      detail?: string
+    }>
     codexSyncRead?: () => unknown
     codexAsyncRead?: () => Promise<unknown>
     updateProviderProfile?: (...args: unknown[]) => unknown
@@ -189,8 +193,12 @@ function mockProviderManagerDependencies(
   })
 
   mock.module('../utils/providerDiscovery.js', () => ({
-    hasLocalOllama: options?.hasLocalOllama ?? (async () => false),
-    listOllamaModels: options?.listOllamaModels ?? (async () => []),
+    probeOllamaGenerationReadiness:
+      options?.probeOllamaGenerationReadiness ??
+      (async () => ({
+        state: 'unreachable' as const,
+        models: [],
+      })),
   }))
 
   mock.module('../utils/githubModelsCredentials.js', () => ({
@@ -455,19 +463,22 @@ test('ProviderManager first-run Ollama preset auto-detects installed models', as
     async () => undefined,
     {
       addProviderProfile,
-      hasLocalOllama: async () => true,
-      listOllamaModels: async () => [
-        {
-          name: 'gemma4:31b-cloud',
-          family: 'gemma',
-          parameterSize: '31b',
-        },
-        {
-          name: 'kimi-k2.5:cloud',
-          family: 'kimi',
-          parameterSize: '2.5b',
-        },
-      ],
+      probeOllamaGenerationReadiness: async () => ({
+        state: 'ready',
+        models: [
+          {
+            name: 'gemma4:31b-cloud',
+            family: 'gemma',
+            parameterSize: '31b',
+          },
+          {
+            name: 'kimi-k2.5:cloud',
+            family: 'kimi',
+            parameterSize: '2.5b',
+          },
+        ],
+        probeModel: 'gemma4:31b-cloud',
+      }),
     },
   )
 
diff --git a/src/components/ProviderManager.tsx b/src/components/ProviderManager.tsx
index 6bf0df28..950c51c2 100644
--- a/src/components/ProviderManager.tsx
+++ b/src/components/ProviderManager.tsx
@@ -37,13 +37,14 @@ import {
   readGithubModelsTokenAsync,
 } from '../utils/githubModelsCredentials.js'
 import {
-  hasLocalOllama,
-  listOllamaModels,
+  probeOllamaGenerationReadiness,
+  type OllamaGenerationReadiness,
 } from '../utils/providerDiscovery.js'
 import {
   rankOllamaModels,
   recommendOllamaModel,
 } from '../utils/providerRecommendation.js'
+import { redactUrlForDisplay } from '../utils/urlRedaction.js'
 import { updateSettingsForSource } from '../utils/settings/settings.js'
 import {
   type OptionWithDescription,
@@ -52,7 +53,6 @@ import {
 import { Pane } from './design-system/Pane.js'
 import TextInput from './TextInput.js'
 import { useCodexOAuthFlow } from './useCodexOAuthFlow.js'
-import { useSetAppState } from '../state/AppState.js'
 
 export type ProviderManagerResult = {
   action: 'saved' | 'cancelled'
@@ -222,6 +222,29 @@ function getGithubProviderSummary(
   return `github-models · ${GITHUB_PROVIDER_DEFAULT_BASE_URL} · ${getGithubProviderModel(processEnv)} · ${credentialSummary}${activeSuffix}`
 }
 
+function describeOllamaSelectionIssue(
+  readiness: OllamaGenerationReadiness,
+  baseUrl: string,
+): string {
+  if (readiness.state === 'unreachable') {
+    return `Could not reach Ollama at ${redactUrlForDisplay(baseUrl)}. Start Ollama first, or enter the endpoint manually.`
+  }
+
+  if (readiness.state === 'no_models') {
+    return 'Ollama is running, but no installed models were found. Pull a chat model such as qwen2.5-coder:7b or llama3.1:8b first, or enter details manually.'
+  }
+
+  if (readiness.state === 'generation_failed') {
+    const modelHint = readiness.probeModel ?? 'the selected model'
+    const detailSuffix = readiness.detail
+      ? ` Details: ${readiness.detail}.`
+      : ''
+    return `Ollama is reachable and models are installed, but a generation probe failed for ${modelHint}.${detailSuffix} Run "ollama run ${modelHint}" once and retry, or enter details manually.`
+  }
+
+  return ''
+}
+
 function findCodexOAuthProfile(
   profiles: ProviderProfile[],
   profileId?: string,
@@ -450,32 +473,21 @@ export function ProviderManager({ mode, onDone }: Props): React.ReactNode {
     setOllamaSelection({ state: 'loading' })
 
     void (async () => {
-      const available = await hasLocalOllama(draft.baseUrl)
-      if (!available) {
+      const readiness = await probeOllamaGenerationReadiness({
+        baseUrl: draft.baseUrl,
+      })
+      if (readiness.state !== 'ready') {
         if (!cancelled) {
           setOllamaSelection({
             state: 'unavailable',
-            message:
-              'Could not reach Ollama. Start Ollama first, or enter the endpoint manually.',
+            message: describeOllamaSelectionIssue(readiness, draft.baseUrl),
           })
         }
         return
       }
 
-      const models = await listOllamaModels(draft.baseUrl)
-      if (models.length === 0) {
-        if (!cancelled) {
-          setOllamaSelection({
-            state: 'unavailable',
-            message:
-              'Ollama is running, but no installed models were found. Pull a chat model such as qwen2.5-coder:7b or llama3.1:8b first, or enter details manually.',
-          })
-        }
-        return
-      }
-
-      const ranked = rankOllamaModels(models, 'balanced')
-      const recommended = recommendOllamaModel(models, 'balanced')
+      const ranked = rankOllamaModels(readiness.models, 'balanced')
+      const recommended = recommendOllamaModel(readiness.models, 'balanced')
       if (!cancelled) {
         setOllamaSelection({
           state: 'ready',
diff --git a/src/components/memory/memoryFileSelectorPaths.test.ts b/src/components/memory/memoryFileSelectorPaths.test.ts
index e3f34401..53fddc13 100644
--- a/src/components/memory/memoryFileSelectorPaths.test.ts
+++ b/src/components/memory/memoryFileSelectorPaths.test.ts
@@ -53,17 +53,20 @@ describe('getProjectMemoryPathForSelector', () => {
   })
 
   test('defaults to a new AGENTS.md in the current cwd when no project file is loaded', () => {
-    expect(getProjectMemoryPathForSelector([], '/repo/packages/app')).toBe(
-      '/repo/packages/app/AGENTS.md',
+    const cwd = join('/repo', 'packages', 'app')
+    expect(getProjectMemoryPathForSelector([], cwd)).toBe(
+      join(cwd, 'AGENTS.md'),
     )
   })
 
   test('ignores loaded project instruction files outside the current cwd ancestry', () => {
+    const outsideRepoPath = join('/other-worktree', 'AGENTS.md')
+    const cwd = join('/repo', 'packages', 'app')
     expect(
       getProjectMemoryPathForSelector(
-        [projectFile('/other-worktree/AGENTS.md')],
-        '/repo/packages/app',
+        [projectFile(outsideRepoPath)],
+        cwd,
       ),
-    ).toBe('/repo/packages/app/AGENTS.md')
+    ).toBe(join(cwd, 'AGENTS.md'))
   })
 })
diff --git a/src/ink/termio/osc.test.ts b/src/ink/termio/osc.test.ts
index d4cfc622..34ee118d 100644
--- a/src/ink/termio/osc.test.ts
+++ b/src/ink/termio/osc.test.ts
@@ -11,14 +11,16 @@ const execFileNoThrowMock = mock(
   async () => ({ code: 0, stdout: '', stderr: '' }),
 )
 
-mock.module('../../utils/execFileNoThrow.js', () => ({
-  execFileNoThrow: execFileNoThrowMock,
-  execFileNoThrowWithCwd: execFileNoThrowMock,
-}))
+function installOscMocks(): void {
+  mock.module('../../utils/execFileNoThrow.js', () => ({
+    execFileNoThrow: execFileNoThrowMock,
+    execFileNoThrowWithCwd: execFileNoThrowMock,
+  }))
 
-mock.module('../../utils/tempfile.js', () => ({
-  generateTempFilePath: generateTempFilePathMock,
-}))
+  mock.module('../../utils/tempfile.js', () => ({
+    generateTempFilePath: generateTempFilePathMock,
+  }))
+}
 
 async function importFreshOscModule() {
   return import(`./osc.ts?ts=${Date.now()}-${Math.random()}`)
@@ -45,6 +47,7 @@ async function waitForExecCall(
 
 describe('Windows clipboard fallback', () => {
   beforeEach(() => {
+    installOscMocks()
     execFileNoThrowMock.mockClear()
     generateTempFilePathMock.mockClear()
     process.env = { ...originalEnv }
@@ -62,14 +65,12 @@ describe('Windows clipboard fallback', () => {
     const { setClipboard } = await importFreshOscModule()
 
     await setClipboard('Привет мир')
-    await flushClipboardCopy()
+    const windowsCall = await waitForExecCall('powershell')
 
     expect(execFileNoThrowMock.mock.calls.some(([cmd]) => cmd === 'clip')).toBe(
       false,
     )
-    expect(
-      execFileNoThrowMock.mock.calls.some(([cmd]) => cmd === 'powershell'),
-    ).toBe(true)
+    expect(windowsCall).toBeDefined()
   })
 
   test('passes Windows clipboard text through a UTF-8 temp file instead of stdin', async () => {
@@ -97,6 +98,7 @@ describe('Windows clipboard fallback', () => {
 
 describe('clipboard path behavior remains stable', () => {
   beforeEach(() => {
+    installOscMocks()
     execFileNoThrowMock.mockClear()
     process.env = { ...originalEnv }
     delete process.env['SSH_CONNECTION']
diff --git a/src/services/api/openaiErrorClassification.ts b/src/services/api/openaiErrorClassification.ts
index 3f86cf96..a18a672a 100644
--- a/src/services/api/openaiErrorClassification.ts
+++ b/src/services/api/openaiErrorClassification.ts
@@ -320,10 +320,7 @@ export function classifyOpenAIHttpFailure(options: {
     }
   }
 
-  if (
-    (options.status >= 200 && options.status < 300 && isMalformedProviderResponse(body)) ||
-    (options.status >= 400 && isMalformedProviderResponse(body))
-  ) {
+  if (options.status >= 400 && isMalformedProviderResponse(body)) {
     return {
       source: 'http',
       category: 'malformed_provider_response',
diff --git a/src/services/api/openaiShim.diagnostics.test.ts b/src/services/api/openaiShim.diagnostics.test.ts
index 9fbcfafd..bf0fe623 100644
--- a/src/services/api/openaiShim.diagnostics.test.ts
+++ b/src/services/api/openaiShim.diagnostics.test.ts
@@ -117,3 +117,170 @@ test('redacts credentials in transport diagnostic URL logs', async () => {
   expect(logLine).not.toContain('user:supersecret')
   expect(logLine).not.toContain('supersecret@')
 })
+test('logs self-heal localhost fallback with redacted from/to URLs', async () => {
+  const debugSpy = mock(() => {})
+  mock.module('../../utils/debug.js', () => ({
+    logForDebugging: debugSpy,
+  }))
+
+  const nonce = `${Date.now()}-${Math.random()}`
+  const { createOpenAIShimClient } = await import(`./openaiShim.ts?ts=${nonce}`)
+
+  process.env.OPENAI_BASE_URL = 'http://user:supersecret@localhost:11434/v1'
+  process.env.OPENAI_API_KEY = 'supersecret'
+
+  globalThis.fetch = mock(async (input: string | Request) => {
+    const url = typeof input === 'string' ? input : input.url
+    if (url.includes('localhost')) {
+      throw Object.assign(new TypeError('fetch failed'), {
+        code: 'ENOTFOUND',
+      })
+    }
+
+    return new Response(
+      JSON.stringify({
+        id: 'chatcmpl-1',
+        model: 'qwen2.5-coder:7b',
+        choices: [
+          {
+            message: {
+              role: 'assistant',
+              content: 'ok',
+            },
+            finish_reason: 'stop',
+          },
+        ],
+        usage: {
+          prompt_tokens: 5,
+          completion_tokens: 2,
+          total_tokens: 7,
+        },
+      }),
+      {
+        status: 200,
+        headers: {
+          'Content-Type': 'application/json',
+        },
+      },
+    )
+  }) as typeof globalThis.fetch
+
+  const client = createOpenAIShimClient({}) as {
+    beta: {
+      messages: {
+        create: (params: Record<string, unknown>) => Promise<unknown>
+      }
+    }
+  }
+
+  await expect(
+    client.beta.messages.create({
+      model: 'qwen2.5-coder:7b',
+      messages: [{ role: 'user', content: 'hello' }],
+      max_tokens: 64,
+      stream: false,
+    }),
+  ).resolves.toBeDefined()
+
+  const fallbackLog = debugSpy.mock.calls.find(call =>
+    typeof call?.[0] === 'string' &&
+    call[0].includes('self-heal retry reason=localhost_resolution_failed'),
+  )
+
+  expect(fallbackLog).toBeDefined()
+  const logLine = String(fallbackLog?.[0])
+  expect(logLine).toContain('from=http://redacted:redacted@localhost:11434/v1/chat/completions')
+  expect(logLine).toContain('to=http://redacted:redacted@127.0.0.1:11434/v1/chat/completions')
+  expect(logLine).not.toContain('supersecret')
+})
+
+test('logs self-heal toolless retry for local tool-call incompatibility', async () => {
+  const debugSpy = mock(() => {})
+  mock.module('../../utils/debug.js', () => ({
+    logForDebugging: debugSpy,
+  }))
+
+  const nonce = `${Date.now()}-${Math.random()}`
+  const { createOpenAIShimClient } = await import(`./openaiShim.ts?ts=${nonce}`)
+
+  process.env.OPENAI_BASE_URL = 'http://localhost:11434/v1'
+  process.env.OPENAI_API_KEY = 'ollama'
+
+  let callCount = 0
+  globalThis.fetch = mock(async () => {
+    callCount += 1
+    if (callCount === 1) {
+      return new Response('tool_calls are not supported', {
+        status: 400,
+        headers: {
+          'Content-Type': 'text/plain',
+        },
+      })
+    }
+
+    return new Response(
+      JSON.stringify({
+        id: 'chatcmpl-1',
+        model: 'qwen2.5-coder:7b',
+        choices: [
+          {
+            message: {
+              role: 'assistant',
+              content: 'ok',
+            },
+            finish_reason: 'stop',
+          },
+        ],
+        usage: {
+          prompt_tokens: 7,
+          completion_tokens: 3,
+          total_tokens: 10,
+        },
+      }),
+      {
+        status: 200,
+        headers: {
+          'Content-Type': 'application/json',
+        },
+      },
+    )
+  }) as typeof globalThis.fetch
+
+  const client = createOpenAIShimClient({}) as {
+    beta: {
+      messages: {
+        create: (params: Record<string, unknown>) => Promise<unknown>
+      }
+    }
+  }
+
+  await expect(
+    client.beta.messages.create({
+      model: 'qwen2.5-coder:7b',
+      messages: [{ role: 'user', content: 'hello' }],
+      tools: [
+        {
+          name: 'Read',
+          description: 'Read file',
+          input_schema: {
+            type: 'object',
+            properties: {
+              filePath: { type: 'string' },
+            },
+            required: ['filePath'],
+          },
+        },
+      ],
+      max_tokens: 64,
+      stream: false,
+    }),
+  ).resolves.toBeDefined()
+
+  const fallbackLog = debugSpy.mock.calls.find(call =>
+    typeof call?.[0] === 'string' &&
+    call[0].includes('self-heal retry reason=tool_call_incompatible mode=toolless'),
+  )
+
+  expect(fallbackLog).toBeDefined()
+  expect(fallbackLog?.[1]).toEqual({ level: 'warn' })
+})
diff --git a/src/services/api/openaiShim.test.ts b/src/services/api/openaiShim.test.ts
index eaf8b590..f4a6bfe9 100644
--- a/src/services/api/openaiShim.test.ts
+++ b/src/services/api/openaiShim.test.ts
@@ -2931,6 +2931,204 @@ test('classifies chat-completions endpoint 404 failures with endpoint_not_found
     }),
   ).rejects.toThrow('openai_category=endpoint_not_found')
 })
+test('self-heals localhost resolution failures by retrying local loopback base URL', async () => {
+  process.env.OPENAI_BASE_URL = 'http://localhost:11434/v1'
+
+  const requestUrls: string[] = []
+  globalThis.fetch = (async (input, _init) => {
+    const url = typeof input === 'string' ? input : input.url
+    requestUrls.push(url)
+
+    if (url.includes('localhost')) {
+      const error = Object.assign(new TypeError('fetch failed'), {
+        code: 'ENOTFOUND',
+      })
+      throw error
+    }
+
+    return new Response(
+      JSON.stringify({
+        id: 'chatcmpl-1',
+        model: 'qwen2.5-coder:7b',
+        choices: [
+          {
+            message: {
+              role: 'assistant',
+              content: 'hello from loopback',
+            },
+            finish_reason: 'stop',
+          },
+        ],
+        usage: {
+          prompt_tokens: 4,
+          completion_tokens: 3,
+          total_tokens: 7,
+        },
+      }),
+      {
+        status: 200,
+        headers: {
+          'Content-Type': 'application/json',
+        },
+      },
+    )
+  }) as FetchType
+
+  const client = createOpenAIShimClient({}) as OpenAIShimClient
+
+  await expect(
+    client.beta.messages.create({
+      model: 'qwen2.5-coder:7b',
+      messages: [{ role: 'user', content: 'hello' }],
+      max_tokens: 64,
+      stream: false,
+    }),
+  ).resolves.toBeDefined()
+
+  expect(requestUrls[0]).toBe('http://localhost:11434/v1/chat/completions')
+  expect(requestUrls).toContain('http://127.0.0.1:11434/v1/chat/completions')
+})
+
+test('self-heals local endpoint_not_found by retrying with /v1 base URL', async () => {
+  process.env.OPENAI_BASE_URL = 'http://localhost:11434'
+
+  const requestUrls: string[] = []
+  globalThis.fetch = (async (input, _init) => {
+    const url = typeof input === 'string' ? input : input.url
+    requestUrls.push(url)
+
+    if (url === 'http://localhost:11434/chat/completions') {
+      return new Response('Not Found', {
+        status: 404,
+        headers: {
+          'Content-Type': 'text/plain',
+        },
+      })
+    }
+
+    return new Response(
+      JSON.stringify({
+        id: 'chatcmpl-1',
+        model: 'qwen2.5-coder:7b',
+        choices: [
+          {
+            message: {
+              role: 'assistant',
+              content: 'hello from /v1',
+            },
+            finish_reason: 'stop',
+          },
+        ],
+        usage: {
+          prompt_tokens: 5,
+          completion_tokens: 2,
+          total_tokens: 7,
+        },
+      }),
+      {
+        status: 200,
+        headers: {
+          'Content-Type': 'application/json',
+        },
+      },
+    )
+  }) as FetchType
+
+  const client = createOpenAIShimClient({}) as OpenAIShimClient
+
+  await expect(
+    client.beta.messages.create({
+      model: 'qwen2.5-coder:7b',
+      messages: [{ role: 'user', content: 'hello' }],
+      max_tokens: 64,
+      stream: false,
+    }),
+  ).resolves.toBeDefined()
+
+  expect(requestUrls).toEqual([
+    'http://localhost:11434/chat/completions',
+    'http://localhost:11434/v1/chat/completions',
+  ])
+})
+
+test('self-heals tool-call incompatibility by retrying local Ollama requests without tools', async () => {
+  process.env.OPENAI_BASE_URL = 'http://localhost:11434/v1'
+
+  const requestBodies: Array<Record<string, unknown>> = []
+  globalThis.fetch = (async (_input, init) => {
+    const requestBody = JSON.parse(String(init?.body)) as Record<string, unknown>
+    requestBodies.push(requestBody)
+
+    if (requestBodies.length === 1) {
+      return new Response('tool_calls are not supported', {
+        status: 400,
+        headers: {
+          'Content-Type': 'text/plain',
+        },
+      })
+    }
+
+    return new Response(
+      JSON.stringify({
+        id: 'chatcmpl-1',
+        model: 'qwen2.5-coder:7b',
+        choices: [
+          {
+            message: {
+              role: 'assistant',
+              content: 'fallback without tools',
+            },
+            finish_reason: 'stop',
+          },
+        ],
+        usage: {
+          prompt_tokens: 8,
+          completion_tokens: 4,
+          total_tokens: 12,
+        },
+      }),
+      {
+        status: 200,
+        headers: {
+          'Content-Type': 'application/json',
+        },
+      },
+    )
+  }) as FetchType
+
+  const client = createOpenAIShimClient({}) as OpenAIShimClient
+
+  await expect(
+    client.beta.messages.create({
+      model: 'qwen2.5-coder:7b',
+      messages: [{ role: 'user', content: 'hello' }],
+      tools: [
+        {
+          name: 'Read',
+          description: 'Read a file',
+          input_schema: {
+            type: 'object',
+            properties: {
+              filePath: { type: 'string' },
+            },
+            required: ['filePath'],
+          },
+        },
+      ],
+      max_tokens: 64,
+      stream: false,
+    }),
+  ).resolves.toBeDefined()
+
+  expect(requestBodies).toHaveLength(2)
+  expect(Array.isArray(requestBodies[0]?.tools)).toBe(true)
+  expect(requestBodies[0]?.tool_choice).toBeUndefined()
+  expect(
+    requestBodies[1]?.tools === undefined ||
+      (Array.isArray(requestBodies[1]?.tools) && requestBodies[1]?.tools.length === 0),
+  ).toBe(true)
+  expect(requestBodies[1]?.tool_choice).toBeUndefined()
+})
 
 test('preserves valid tool_result and drops orphan tool_result', async () => {
   let requestBody: Record<string, unknown> | undefined
@@ -2999,7 +3197,7 @@ test('preserves valid tool_result and drops orphan tool_result', async () => {
           {
             role: 'user',
             content: 'What happened?',
-          }
+          },
         ],
       },
     ],
@@ -3008,14 +3206,14 @@ test('preserves valid tool_result and drops orphan tool_result', async () => {
   })
 
   const messages = requestBody?.messages as Array<Record<string, unknown>>
-  
+
   // Should have: system, user, assistant (tool_use), tool (valid_call_1), user
   // Should NOT have: tool (orphan_call_2)
-  
+
   const toolMessages = messages.filter(m => m.role === 'tool')
   expect(toolMessages.length).toBe(1)
   expect(toolMessages[0].tool_call_id).toBe('valid_call_1')
-  
+
   const orphanMessage = toolMessages.find(m => m.tool_call_id === 'orphan_call_2')
   expect(orphanMessage).toBeUndefined()
 })
diff --git a/src/services/api/openaiShim.ts b/src/services/api/openaiShim.ts
index 6c3c1ffa..e506fc97 100644
--- a/src/services/api/openaiShim.ts
+++ b/src/services/api/openaiShim.ts
@@ -48,10 +48,12 @@ import {
 } from './codexShim.js'
 import { fetchWithProxyRetry } from './fetchWithProxyRetry.js'
 import {
+  getLocalProviderRetryBaseUrls,
+  getGithubEndpointType,
   isLocalProviderUrl,
   resolveRuntimeCodexCredentials,
   resolveProviderRequest,
-  getGithubEndpointType,
+  shouldAttemptLocalToollessRetry,
 } from './providerConfig.js'
 import {
   buildOpenAICompatibilityErrorMessage,
@@ -1427,48 +1429,95 @@ class OpenAIShimMessages {
       headers['X-GitHub-Api-Version'] = '2022-11-28'
     }
 
-    // Build the chat completions URL
-    // Azure Cognitive Services / Azure OpenAI require a deployment-specific path
-    // and an api-version query parameter.
-    // Standard format: {base}/openai/deployments/{model}/chat/completions?api-version={version}
-    // Non-Azure: {base}/chat/completions
-    let chatCompletionsUrl: string
-    if (isAzure) {
-      const apiVersion = process.env.AZURE_OPENAI_API_VERSION ?? '2024-12-01-preview'
-      const deployment = request.resolvedModel ?? process.env.OPENAI_MODEL ?? 'gpt-4o'
-      // If base URL already contains /deployments/, use it as-is with api-version
-      if (/\/deployments\//i.test(request.baseUrl)) {
-        const base = request.baseUrl.replace(/\/+$/, '')
-        chatCompletionsUrl = `${base}/chat/completions?api-version=${apiVersion}`
-      } else {
-        // Strip trailing /v1 or /openai/v1 if present, then build Azure path
-        const base = request.baseUrl.replace(/\/(openai\/)?v1\/?$/, '').replace(/\/+$/, '')
-        chatCompletionsUrl = `${base}/openai/deployments/${deployment}/chat/completions?api-version=${apiVersion}`
+    const buildChatCompletionsUrl = (baseUrl: string): string => {
+      // Azure Cognitive Services / Azure OpenAI require a deployment-specific
+      // path and an api-version query parameter.
+      if (isAzure) {
+        const apiVersion = process.env.AZURE_OPENAI_API_VERSION ?? '2024-12-01-preview'
+        const deployment = request.resolvedModel ?? process.env.OPENAI_MODEL ?? 'gpt-4o'
+
+        // If base URL already contains /deployments/, use it as-is with api-version.
+        if (/\/deployments\//i.test(baseUrl)) {
+          const normalizedBase = baseUrl.replace(/\/+$/, '')
+          return `${normalizedBase}/chat/completions?api-version=${apiVersion}`
+        }
+
+        // Strip trailing /v1 or /openai/v1 if present, then build Azure path.
+        const normalizedBase = baseUrl
+          .replace(/\/(openai\/)?v1\/?$/, '')
+          .replace(/\/+$/, '')
+
+        return `${normalizedBase}/openai/deployments/${deployment}/chat/completions?api-version=${apiVersion}`
       }
-    } else {
-      chatCompletionsUrl = `${request.baseUrl}/chat/completions`
+
+      return `${baseUrl}/chat/completions`
     }
 
-    const fetchInit = {
+    const localRetryBaseUrls = isLocal
+      ? getLocalProviderRetryBaseUrls(request.baseUrl)
+      : []
+
+    let activeBaseUrl = request.baseUrl
+    let chatCompletionsUrl = buildChatCompletionsUrl(activeBaseUrl)
+    const attemptedLocalBaseUrls = new Set<string>([activeBaseUrl])
+    let didRetryWithoutTools = false
+
+    const promoteNextLocalBaseUrl = (
+      reason: 'endpoint_not_found' | 'localhost_resolution_failed',
+    ): boolean => {
+      for (const candidateBaseUrl of localRetryBaseUrls) {
+        if (attemptedLocalBaseUrls.has(candidateBaseUrl)) {
+          continue
+        }
+
+        const previousUrl = chatCompletionsUrl
+        attemptedLocalBaseUrls.add(candidateBaseUrl)
+        activeBaseUrl = candidateBaseUrl
+        chatCompletionsUrl = buildChatCompletionsUrl(activeBaseUrl)
+
+        logForDebugging(
+          `[OpenAIShim] self-heal retry reason=${reason} method=POST from=${redactUrlForDiagnostics(previousUrl)} to=${redactUrlForDiagnostics(chatCompletionsUrl)} model=${request.resolvedModel}`,
+          { level: 'warn' },
+        )
+
+        return true
+      }
+
+      return false
+    }
+
+    let serializedBody = JSON.stringify(body)
+
+    const refreshSerializedBody = (): void => {
+      serializedBody = JSON.stringify(body)
+    }
+
+    const buildFetchInit = () => ({
       method: 'POST' as const,
       headers,
-      body: JSON.stringify(body),
+      body: serializedBody,
       signal: options?.signal,
-    }
+    })
 
-    const maxAttempts = isGithub ? GITHUB_429_MAX_RETRIES : 1
+    const maxSelfHealAttempts = isLocal
+      ? localRetryBaseUrls.length + 1
+      : 0
+    const maxAttempts = (isGithub ? GITHUB_429_MAX_RETRIES : 1) + maxSelfHealAttempts
 
     const throwClassifiedTransportError = (
       error: unknown,
       requestUrl: string,
+      preclassifiedFailure?: ReturnType<typeof classifyOpenAINetworkFailure>,
     ): never => {
       if (options?.signal?.aborted) {
         throw error
       }
 
-      const failure = classifyOpenAINetworkFailure(error, {
-        url: requestUrl,
-      })
+      const failure =
+        preclassifiedFailure ??
+        classifyOpenAINetworkFailure(error, {
+          url: requestUrl,
+        })
       const redactedUrl = redactUrlForDiagnostics(requestUrl)
       const safeMessage =
         redactSecretValueForDisplay(
@@ -1499,11 +1548,14 @@ class OpenAIShimMessages {
       responseHeaders: Headers,
       requestUrl: string,
       rateHint = '',
+      preclassifiedFailure?: ReturnType<typeof classifyOpenAIHttpFailure>,
     ): never => {
-      const failure = classifyOpenAIHttpFailure({
-        status,
-        body: errorBody,
-      })
+      const failure =
+        preclassifiedFailure ??
+        classifyOpenAIHttpFailure({
+          status,
+          body: errorBody,
+        })
       const redactedUrl = redactUrlForDiagnostics(requestUrl)
 
       logForDebugging(
@@ -1525,10 +1577,13 @@ class OpenAIShimMessages {
     let response: Response | undefined
     for (let attempt = 0; attempt < maxAttempts; attempt++) {
       try {
-        response = await fetchWithProxyRetry(chatCompletionsUrl, fetchInit)
+        response = await fetchWithProxyRetry(
+          chatCompletionsUrl,
+          buildFetchInit(),
+        )
       } catch (error) {
         const isAbortError =
-          fetchInit.signal?.aborted === true ||
+          options?.signal?.aborted === true ||
           (typeof DOMException !== 'undefined' &&
             error instanceof DOMException &&
             error.name === 'AbortError') ||
@@ -1541,7 +1596,19 @@ class OpenAIShimMessages {
           throw error
         }
 
-        throwClassifiedTransportError(error, chatCompletionsUrl)
+        const failure = classifyOpenAINetworkFailure(error, {
+          url: chatCompletionsUrl,
+        })
+
+        if (
+          isLocal &&
+          failure.category === 'localhost_resolution_failed' &&
+          promoteNextLocalBaseUrl('localhost_resolution_failed')
+        ) {
+          continue
+        }
+
+        throwClassifiedTransportError(error, chatCompletionsUrl, failure)
       }
 
       if (response.ok) {
@@ -1633,6 +1700,10 @@ class OpenAIShimMessages {
             return responsesResponse
           }
           const responsesErrorBody = await responsesResponse.text().catch(() => 'unknown error')
+          const responsesFailure = classifyOpenAIHttpFailure({
+            status: responsesResponse.status,
+            body: responsesErrorBody,
+          })
           let responsesErrorResponse: object | undefined
           try { responsesErrorResponse = JSON.parse(responsesErrorBody) } catch { /* raw text */ }
           throwClassifiedHttpError(
@@ -1641,10 +1712,49 @@ class OpenAIShimMessages {
             responsesErrorResponse,
             responsesResponse.headers,
             responsesUrl,
+            '',
+            responsesFailure,
           )
         }
       }
 
+      const failure = classifyOpenAIHttpFailure({
+        status: response.status,
+        body: errorBody,
+      })
+
+      if (
+        isLocal &&
+        failure.category === 'endpoint_not_found' &&
+        promoteNextLocalBaseUrl('endpoint_not_found')
+      ) {
+        continue
+      }
+
+      const hasToolsPayload =
+        Array.isArray(body.tools) &&
+        body.tools.length > 0
+
+      if (
+        !didRetryWithoutTools &&
+        failure.category === 'tool_call_incompatible' &&
+        shouldAttemptLocalToollessRetry({
+          baseUrl: activeBaseUrl,
+          hasTools: hasToolsPayload,
+        })
+      ) {
+        didRetryWithoutTools = true
+        delete body.tools
+        delete body.tool_choice
+        refreshSerializedBody()
+
+        logForDebugging(
+          `[OpenAIShim] self-heal retry reason=tool_call_incompatible mode=toolless method=POST url=${redactUrlForDiagnostics(chatCompletionsUrl)} model=${request.resolvedModel}`,
+          { level: 'warn' },
+        )
+        continue
+      }
+
       let errorResponse: object | undefined
       try { errorResponse = JSON.parse(errorBody) } catch { /* raw text */ }
       throwClassifiedHttpError(
@@ -1654,6 +1764,7 @@ class OpenAIShimMessages {
         response.headers as unknown as Headers,
         chatCompletionsUrl,
         rateHint,
+        failure,
       )
     }
 
diff --git a/src/services/api/providerConfig.local.test.ts b/src/services/api/providerConfig.local.test.ts
index 9622998c..eac5ab11 100644
--- a/src/services/api/providerConfig.local.test.ts
+++ b/src/services/api/providerConfig.local.test.ts
@@ -2,8 +2,10 @@ import { afterEach, expect, test } from 'bun:test'
 
 import {
   getAdditionalModelOptionsCacheScope,
+  getLocalProviderRetryBaseUrls,
   isLocalProviderUrl,
   resolveProviderRequest,
+  shouldAttemptLocalToollessRetry,
 } from './providerConfig.js'
 
 const originalEnv = {
@@ -83,3 +85,42 @@ test('skips local model cache scope for remote openai-compatible providers', ()
 
   expect(getAdditionalModelOptionsCacheScope()).toBeNull()
 })
+
+test('derives local retry base URLs with /v1 and loopback fallback candidates', () => {
+  expect(getLocalProviderRetryBaseUrls('http://localhost:11434')).toEqual([
+    'http://localhost:11434/v1',
+    'http://127.0.0.1:11434',
+    'http://127.0.0.1:11434/v1',
+  ])
+})
+
+test('does not derive local retry base URLs for remote providers', () => {
+  expect(getLocalProviderRetryBaseUrls('https://api.openai.com/v1')).toEqual([])
+})
+
+test('enables local toolless retry for likely Ollama endpoints with tools', () => {
+  expect(
+    shouldAttemptLocalToollessRetry({
+      baseUrl: 'http://localhost:11434/v1',
+      hasTools: true,
+    }),
+  ).toBe(true)
+})
+
+test('disables local toolless retry when no tools are present', () => {
+  expect(
+    shouldAttemptLocalToollessRetry({
+      baseUrl: 'http://localhost:11434/v1',
+      hasTools: false,
+    }),
+  ).toBe(false)
+})
+
+test('disables local toolless retry for non-Ollama local endpoints', () => {
+  expect(
+    shouldAttemptLocalToollessRetry({
+      baseUrl: 'http://localhost:1234/v1',
+      hasTools: true,
+    }),
+  ).toBe(false)
+})
diff --git a/src/services/api/providerConfig.ts b/src/services/api/providerConfig.ts
index e84cab98..27d55cfa 100644
--- a/src/services/api/providerConfig.ts
+++ b/src/services/api/providerConfig.ts
@@ -305,6 +305,101 @@ export function isLocalProviderUrl(baseUrl: string | undefined): boolean {
   }
 }
 
+function trimTrailingSlash(value: string): string {
+  return value.replace(/\/+$/, '')
+}
+
+function normalizePathWithV1(pathname: string): string {
+  const trimmed = trimTrailingSlash(pathname)
+  if (!trimmed || trimmed === '/') {
+    return '/v1'
+  }
+
+  if (trimmed.toLowerCase().endsWith('/v1')) {
+    return trimmed
+  }
+
+  return `${trimmed}/v1`
+}
+
+function isLikelyOllamaEndpoint(baseUrl: string): boolean {
+  try {
+    const parsed = new URL(baseUrl)
+    const hostname = parsed.hostname.toLowerCase()
+    const pathname = parsed.pathname.toLowerCase()
+
+    if (parsed.port === '11434') {
+      return true
+    }
+
+    return (
+      hostname.includes('ollama') ||
+      pathname.includes('ollama')
+    )
+  } catch {
+    return false
+  }
+}
+
+export function getLocalProviderRetryBaseUrls(baseUrl: string): string[] {
+  if (!isLocalProviderUrl(baseUrl)) {
+    return []
+  }
+
+  try {
+    const parsed = new URL(baseUrl)
+    const original = trimTrailingSlash(parsed.toString())
+    const seen = new Set<string>([original])
+    const candidates: string[] = []
+
+    const addCandidate = (hostname: string, pathname: string): void => {
+      const next = new URL(parsed.toString())
+      next.hostname = hostname
+      next.pathname = pathname
+      next.search = ''
+      next.hash = ''
+
+      const normalized = trimTrailingSlash(next.toString())
+      if (seen.has(normalized)) {
+        return
+      }
+
+      seen.add(normalized)
+      candidates.push(normalized)
+    }
+
+    const v1Pathname = normalizePathWithV1(parsed.pathname)
+    if (v1Pathname !== trimTrailingSlash(parsed.pathname)) {
+      addCandidate(parsed.hostname, v1Pathname)
+    }
+
+    const hostname = parsed.hostname.toLowerCase().replace(/^\[|\]$/g, '')
+    if (hostname === 'localhost' || hostname === '::1') {
+      addCandidate('127.0.0.1', parsed.pathname || '/')
+      addCandidate('127.0.0.1', v1Pathname)
+    }
+
+    return candidates
+  } catch {
+    return []
+  }
+}
+
+export function shouldAttemptLocalToollessRetry(options: {
+  baseUrl: string
+  hasTools: boolean
+}): boolean {
+  if (!options.hasTools) {
+    return false
+  }
+
+  if (!isLocalProviderUrl(options.baseUrl)) {
+    return false
+  }
+
+  return isLikelyOllamaEndpoint(options.baseUrl)
+}
+
 export function isCodexBaseUrl(baseUrl: string | undefined): boolean {
   if (!baseUrl) return false
   try {
@@ -412,6 +507,9 @@ export function resolveProviderRequest(options?: {
     ? normalizedGeminiEnvBaseUrl
     : asNamedEnvUrl(process.env.OPENAI_BASE_URL, 'OPENAI_BASE_URL')
 
+  // In Mistral mode, a literal "undefined" MISTRAL_BASE_URL is treated as
+  // misconfiguration and falls back to OPENAI_API_BASE, then
+  // DEFAULT_MISTRAL_BASE_URL for a safe default endpoint.
   const fallbackEnvBaseUrl = isMistralMode
     ? (primaryEnvBaseUrl === undefined
       ? asNamedEnvUrl(process.env.OPENAI_API_BASE, 'OPENAI_API_BASE') ?? DEFAULT_MISTRAL_BASE_URL
diff --git a/src/services/autoFix/autoFixRunner.test.ts b/src/services/autoFix/autoFixRunner.test.ts
index 616d6170..56465f84 100644
--- a/src/services/autoFix/autoFixRunner.test.ts
+++ b/src/services/autoFix/autoFixRunner.test.ts
@@ -70,7 +70,7 @@ describe('runAutoFixCheck', () => {
 
   test('handles timeout gracefully', async () => {
     const result = await runAutoFixCheck({
-      lint: 'sleep 10',
+      lint: 'node -e "setTimeout(() => {}, 10000)"',
       timeout: 100,
 
       cwd: '/tmp',
diff --git a/src/services/autoFix/autoFixRunner.ts b/src/services/autoFix/autoFixRunner.ts
index a24268a7..48907e0e 100644
--- a/src/services/autoFix/autoFixRunner.ts
+++ b/src/services/autoFix/autoFixRunner.ts
@@ -46,14 +46,31 @@ async function runCommand(
 
     const killTree = () => {
       try {
-        if (!isWindows && proc.pid) {
+        if (isWindows && proc.pid) {
+          // shell=true on Windows can leave child commands running unless we
+          // terminate the full process tree.
+          const killer = spawn('taskkill', ['/pid', String(proc.pid), '/T', '/F'], {
+            windowsHide: true,
+            stdio: 'ignore',
+          })
+          killer.unref()
+          return
+        }
+
+        if (proc.pid) {
           // Kill the entire process group
           process.kill(-proc.pid, 'SIGTERM')
-        } else {
-          proc.kill('SIGTERM')
+          return
         }
+
+        proc.kill('SIGTERM')
       } catch {
-        // Process may have already exited
+        // Process may have already exited; fallback to direct child kill.
+        try {
+          proc.kill('SIGTERM')
+        } catch {
+          // Ignore final fallback errors.
+        }
       }
     }
 
diff --git a/src/services/wiki/init.test.ts b/src/services/wiki/init.test.ts
index db767366..ecd10bb6 100644
--- a/src/services/wiki/init.test.ts
+++ b/src/services/wiki/init.test.ts
@@ -26,10 +26,10 @@ test('initializeWiki creates the expected wiki scaffold', async () => {
 
   expect(result.alreadyExisted).toBe(false)
   expect(result.createdFiles).toEqual([
-    '.openclaude/wiki/schema.md',
-    '.openclaude/wiki/index.md',
-    '.openclaude/wiki/log.md',
-    '.openclaude/wiki/pages/architecture.md',
+    join('.openclaude', 'wiki', 'schema.md'),
+    join('.openclaude', 'wiki', 'index.md'),
+    join('.openclaude', 'wiki', 'log.md'),
+    join('.openclaude', 'wiki', 'pages', 'architecture.md'),
   ])
   expect(await readFile(paths.schemaFile, 'utf8')).toContain(
     '# OpenClaude Wiki Schema',
diff --git a/src/utils/localInstaller.ts b/src/utils/localInstaller.ts
index b2f4e678..824c10dc 100644
--- a/src/utils/localInstaller.ts
+++ b/src/utils/localInstaller.ts
@@ -44,9 +44,10 @@ function getCandidateLocalBinaryPaths(localInstallDir: string): string[] {
 }
 
 export function isManagedLocalInstallationPath(execPath: string): boolean {
+  const normalizedExecPath = execPath.replace(/\\+/g, '/')
   return (
-    execPath.includes('/.openclaude/local/node_modules/') ||
-    execPath.includes('/.claude/local/node_modules/')
+    normalizedExecPath.includes('/.openclaude/local/node_modules/') ||
+    normalizedExecPath.includes('/.claude/local/node_modules/')
   )
 }
 
diff --git a/src/utils/providerDiscovery.test.ts b/src/utils/providerDiscovery.test.ts
index acf62748..1f6bfa89 100644
--- a/src/utils/providerDiscovery.test.ts
+++ b/src/utils/providerDiscovery.test.ts
@@ -1,9 +1,9 @@
 import { afterEach, expect, mock, test } from 'bun:test'
 
-import {
-  getLocalOpenAICompatibleProviderLabel,
-  listOpenAICompatibleModels,
-} from './providerDiscovery.js'
+async function loadProviderDiscoveryModule() {
+  // @ts-expect-error cache-busting query string for Bun module mocks
+  return import(`./providerDiscovery.js?ts=${Date.now()}-${Math.random()}`)
+}
 
 const originalFetch = globalThis.fetch
 const originalEnv = {
@@ -16,6 +16,8 @@ afterEach(() => {
 })
 
 test('lists models from a local openai-compatible /models endpoint', async () => {
+  const { listOpenAICompatibleModels } = await loadProviderDiscoveryModule()
+
   globalThis.fetch = mock((input, init) => {
     const url = typeof input === 'string' ? input : input.url
     expect(url).toBe('http://localhost:1234/v1/models')
@@ -47,6 +49,8 @@ test('lists models from a local openai-compatible /models endpoint', async () =>
 })
 
 test('returns null when a local openai-compatible /models request fails', async () => {
+  const { listOpenAICompatibleModels } = await loadProviderDiscoveryModule()
+
   globalThis.fetch = mock(() =>
     Promise.resolve(new Response('not available', { status: 503 })),
   ) as typeof globalThis.fetch
@@ -56,13 +60,19 @@ test('returns null when a local openai-compatible /models request fails', async
   ).resolves.toBeNull()
 })
 
-test('detects LM Studio from the default localhost port', () => {
+test('detects LM Studio from the default localhost port', async () => {
+  const { getLocalOpenAICompatibleProviderLabel } =
+    await loadProviderDiscoveryModule()
+
   expect(getLocalOpenAICompatibleProviderLabel('http://localhost:1234/v1')).toBe(
     'LM Studio',
   )
 })
 
-test('detects common local openai-compatible providers by hostname', () => {
+test('detects common local openai-compatible providers by hostname', async () => {
+  const { getLocalOpenAICompatibleProviderLabel } =
+    await loadProviderDiscoveryModule()
+
   expect(
     getLocalOpenAICompatibleProviderLabel('http://localai.local:8080/v1'),
   ).toBe('LocalAI')
@@ -71,8 +81,212 @@ test('detects common local openai-compatible providers by hostname', () => {
   ).toBe('vLLM')
 })
 
-test('falls back to a generic local openai-compatible label', () => {
+test('falls back to a generic local openai-compatible label', async () => {
+  const { getLocalOpenAICompatibleProviderLabel } =
+    await loadProviderDiscoveryModule()
+
   expect(
     getLocalOpenAICompatibleProviderLabel('http://127.0.0.1:8080/v1'),
   ).toBe('Local OpenAI-compatible')
+})
+
+test('ollama generation readiness reports unreachable when tags endpoint is down', async () => {
+  const { probeOllamaGenerationReadiness } = await loadProviderDiscoveryModule()
+
+  const calledUrls: string[] = []
+  globalThis.fetch = mock(input => {
+    const url = typeof input === 'string' ? input : input.url
+    calledUrls.push(url)
+    return Promise.resolve(new Response('not available', { status: 503 }))
+  }) as typeof globalThis.fetch
+
+  await expect(
+    probeOllamaGenerationReadiness({
+      baseUrl: 'http://localhost:11434',
+    }),
+  ).resolves.toMatchObject({
+    state: 'unreachable',
+    models: [],
+  })
+
+  expect(calledUrls).toEqual([
+    'http://localhost:11434/api/tags',
+  ])
+})
+
+test('ollama generation readiness reports no models when server is reachable', async () => {
+  const { probeOllamaGenerationReadiness } = await loadProviderDiscoveryModule()
+
+  const calledUrls: string[] = []
+  globalThis.fetch = mock(input => {
+    const url = typeof input === 'string' ? input : input.url
+    calledUrls.push(url)
+    return Promise.resolve(
+      new Response(JSON.stringify({ models: [] }), {
+        status: 200,
+        headers: { 'Content-Type': 'application/json' },
+      }),
+    )
+  }) as typeof globalThis.fetch
+
+  await expect(
+    probeOllamaGenerationReadiness({
+      baseUrl: 'http://localhost:11434',
+    }),
+  ).resolves.toMatchObject({
+    state: 'no_models',
+    models: [],
+  })
+
+  expect(calledUrls).toEqual([
+    'http://localhost:11434/api/tags',
+  ])
+})
+
+test('ollama generation readiness reports generation_failed when requested model is missing', async () => {
+  const { probeOllamaGenerationReadiness } = await loadProviderDiscoveryModule()
+
+  const calledUrls: string[] = []
+  globalThis.fetch = mock(input => {
+    const url = typeof input === 'string' ? input : input.url
+    calledUrls.push(url)
+    return Promise.resolve(
+      new Response(
+        JSON.stringify({
+          models: [{ name: 'llama3.1:8b', size: 1024 }],
+        }),
+        {
+          status: 200,
+          headers: { 'Content-Type': 'application/json' },
+        },
+      ),
+    )
+  }) as typeof globalThis.fetch
+
+  await expect(
+    probeOllamaGenerationReadiness({
+      baseUrl: 'http://localhost:11434',
+      model: 'qwen2.5-coder:7b',
+    }),
+  ).resolves.toMatchObject({
+    state: 'generation_failed',
+    probeModel: 'qwen2.5-coder:7b',
+    detail: 'requested model not installed: qwen2.5-coder:7b',
+  })
+
+  expect(calledUrls).toEqual(['http://localhost:11434/api/tags'])
+})
+
+test('ollama generation readiness reports generation failures when chat probe fails', async () => {
+  const { probeOllamaGenerationReadiness } = await loadProviderDiscoveryModule()
+
+  globalThis.fetch = mock(input => {
+    const url = typeof input === 'string' ? input : input.url
+    if (url.endsWith('/api/tags')) {
+      return Promise.resolve(
+        new Response(
+          JSON.stringify({
+            models: [{ name: 'qwen2.5-coder:7b', size: 42 }],
+          }),
+          {
+            status: 200,
+            headers: { 'Content-Type': 'application/json' },
+          },
+        ),
+      )
+    }
+
+    return Promise.resolve(new Response('model not found', { status: 404 }))
+  }) as typeof globalThis.fetch
+
+  await expect(
+    probeOllamaGenerationReadiness({
+      baseUrl: 'http://localhost:11434',
+      model: 'qwen2.5-coder:7b',
+    }),
+  ).resolves.toMatchObject({
+    state: 'generation_failed',
+    probeModel: 'qwen2.5-coder:7b',
+  })
+})
+
+test('ollama generation readiness reports generation_failed when chat probe returns invalid JSON', async () => {
+  const { probeOllamaGenerationReadiness } = await loadProviderDiscoveryModule()
+
+  globalThis.fetch = mock(input => {
+    const url = typeof input === 'string' ? input : input.url
+    if (url.endsWith('/api/tags')) {
+      return Promise.resolve(
+        new Response(
+          JSON.stringify({
+            models: [{ name: 'llama3.1:8b', size: 1024 }],
+          }),
+          {
+            status: 200,
+            headers: { 'Content-Type': 'application/json' },
+          },
+        ),
+      )
+    }
+
+    return Promise.resolve(
+      new Response('<html>proxy error</html>', {
+        status: 200,
+        headers: { 'Content-Type': 'text/html' },
+      }),
+    )
+  }) as typeof globalThis.fetch
+
+  await expect(
+    probeOllamaGenerationReadiness({
+      baseUrl: 'http://localhost:11434',
+    }),
+  ).resolves.toMatchObject({
+    state: 'generation_failed',
+    probeModel: 'llama3.1:8b',
+    detail: 'invalid JSON response',
+  })
+})
+
+test('ollama generation readiness reports ready when chat probe succeeds', async () => {
+  const { probeOllamaGenerationReadiness } = await loadProviderDiscoveryModule()
+
+  globalThis.fetch = mock(input => {
+    const url = typeof input === 'string' ? input : input.url
+    if (url.endsWith('/api/tags')) {
+      return Promise.resolve(
+        new Response(
+          JSON.stringify({
+            models: [{ name: 'llama3.1:8b', size: 1024 }],
+          }),
+          {
+            status: 200,
+            headers: { 'Content-Type': 'application/json' },
+          },
+        ),
+      )
+    }
+
+    return Promise.resolve(
+      new Response(
+        JSON.stringify({
+          message: { role: 'assistant', content: 'OK' },
+          done: true,
+        }),
+        {
+          status: 200,
+          headers: { 'Content-Type': 'application/json' },
+        },
+      ),
+    )
+  }) as typeof globalThis.fetch
+
+  await expect(
+    probeOllamaGenerationReadiness({
+      baseUrl: 'http://localhost:11434',
+    }),
+  ).resolves.toMatchObject({
+    state: 'ready',
+    probeModel: 'llama3.1:8b',
+  })
 })
\ No newline at end of file
diff --git a/src/utils/providerDiscovery.ts b/src/utils/providerDiscovery.ts
index 89a21d01..8bc64565 100644
--- a/src/utils/providerDiscovery.ts
+++ b/src/utils/providerDiscovery.ts
@@ -4,6 +4,13 @@ import { DEFAULT_OPENAI_BASE_URL } from '../services/api/providerConfig.js'
 export const DEFAULT_OLLAMA_BASE_URL = 'http://localhost:11434'
 export const DEFAULT_ATOMIC_CHAT_BASE_URL = 'http://127.0.0.1:1337'
 
+export type OllamaGenerationReadiness = {
+  state: 'ready' | 'unreachable' | 'no_models' | 'generation_failed'
+  models: OllamaModelDescriptor[]
+  probeModel?: string
+  detail?: string
+}
+
 function withTimeoutSignal(timeoutMs: number): {
   signal: AbortSignal
   clear: () => void
@@ -20,6 +27,83 @@ function trimTrailingSlash(value: string): string {
   return value.replace(/\/+$/, '')
 }
 
+function compactDetail(value: string, maxLength = 180): string {
+  const compact = value.trim().replace(/\s+/g, ' ')
+  if (!compact) {
+    return ''
+  }
+
+  if (compact.length <= maxLength) {
+    return compact
+  }
+
+  return `${compact.slice(0, maxLength)}...`
+}
+
+type OllamaTagsPayload = {
+  models?: Array<{
+    name?: string
+    size?: number
+    details?: {
+      family?: string
+      families?: string[]
+      parameter_size?: string
+      quantization_level?: string
+    }
+  }>
+}
+
+function normalizeOllamaModels(
+  payload: OllamaTagsPayload,
+): OllamaModelDescriptor[] {
+  return (payload.models ?? [])
+    .filter(model => Boolean(model.name))
+    .map(model => ({
+      name: model.name!,
+      sizeBytes: typeof model.size === 'number' ? model.size : null,
+      family: model.details?.family ?? null,
+      families: model.details?.families ?? [],
+      parameterSize: model.details?.parameter_size ?? null,
+      quantizationLevel: model.details?.quantization_level ?? null,
+    }))
+}
+
+async function fetchOllamaModelsProbe(
+  baseUrl?: string,
+  timeoutMs = 5000,
+): Promise<{
+  reachable: boolean
+  models: OllamaModelDescriptor[]
+}> {
+  const { signal, clear } = withTimeoutSignal(timeoutMs)
+  try {
+    const response = await fetch(`${getOllamaApiBaseUrl(baseUrl)}/api/tags`, {
+      method: 'GET',
+      signal,
+    })
+
+    if (!response.ok) {
+      return {
+        reachable: false,
+        models: [],
+      }
+    }
+
+    const payload = (await response.json().catch(() => ({}))) as OllamaTagsPayload
+    return {
+      reachable: true,
+      models: normalizeOllamaModels(payload),
+    }
+  } catch {
+    return {
+      reachable: false,
+      models: [],
+    }
+  } finally {
+    clear()
+  }
+}
+
 export function getOllamaApiBaseUrl(baseUrl?: string): string {
   const parsed = new URL(
     baseUrl || process.env.OLLAMA_BASE_URL || DEFAULT_OLLAMA_BASE_URL,
@@ -121,61 +205,15 @@ export function getLocalOpenAICompatibleProviderLabel(baseUrl?: string): string
 }
 
 export async function hasLocalOllama(baseUrl?: string): Promise<boolean> {
-  const { signal, clear } = withTimeoutSignal(1200)
-  try {
-    const response = await fetch(`${getOllamaApiBaseUrl(baseUrl)}/api/tags`, {
-      method: 'GET',
-      signal,
-    })
-    return response.ok
-  } catch {
-    return false
-  } finally {
-    clear()
-  }
+  const { reachable } = await fetchOllamaModelsProbe(baseUrl, 1200)
+  return reachable
 }
 
 export async function listOllamaModels(
   baseUrl?: string,
 ): Promise<OllamaModelDescriptor[]> {
-  const { signal, clear } = withTimeoutSignal(5000)
-  try {
-    const response = await fetch(`${getOllamaApiBaseUrl(baseUrl)}/api/tags`, {
-      method: 'GET',
-      signal,
-    })
-    if (!response.ok) {
-      return []
-    }
-
-    const data = (await response.json()) as {
-      models?: Array<{
-        name?: string
-        size?: number
-        details?: {
-          family?: string
-          families?: string[]
-          parameter_size?: string
-          quantization_level?: string
-        }
-      }>
-    }
-
-    return (data.models ?? [])
-      .filter(model => Boolean(model.name))
-      .map(model => ({
-        name: model.name!,
-        sizeBytes: typeof model.size === 'number' ? model.size : null,
-        family: model.details?.family ?? null,
-        families: model.details?.families ?? [],
-        parameterSize: model.details?.parameter_size ?? null,
-        quantizationLevel: model.details?.quantization_level ?? null,
-      }))
-  } catch {
-    return []
-  } finally {
-    clear()
-  }
+  const { models } = await fetchOllamaModelsProbe(baseUrl, 5000)
+  return models
 }
 
 export async function listOpenAICompatibleModels(options?: {
@@ -294,3 +332,106 @@ export async function benchmarkOllamaModel(
     clear()
   }
 }
+
+export async function probeOllamaGenerationReadiness(options?: {
+  baseUrl?: string
+  model?: string
+  timeoutMs?: number
+}): Promise<OllamaGenerationReadiness> {
+  const timeoutMs = options?.timeoutMs ?? 8000
+  const { reachable, models } = await fetchOllamaModelsProbe(
+    options?.baseUrl,
+    timeoutMs,
+  )
+  if (!reachable) {
+    return {
+      state: 'unreachable',
+      models: [],
+    }
+  }
+
+  if (models.length === 0) {
+    return {
+      state: 'no_models',
+      models: [],
+    }
+  }
+
+  const requestedModel = options?.model?.trim() || undefined
+  if (requestedModel && !models.some(model => model.name === requestedModel)) {
+    return {
+      state: 'generation_failed',
+      models,
+      probeModel: requestedModel,
+      detail: `requested model not installed: ${requestedModel}`,
+    }
+  }
+
+  const probeModel = requestedModel ?? models[0]!.name
+  const { signal, clear } = withTimeoutSignal(timeoutMs)
+
+  try {
+    const response = await fetch(`${getOllamaApiBaseUrl(options?.baseUrl)}/api/chat`, {
+      method: 'POST',
+      headers: {
+        'Content-Type': 'application/json',
+      },
+      signal,
+      body: JSON.stringify({
+        model: probeModel,
+        stream: false,
+        messages: [{ role: 'user', content: 'Reply with OK.' }],
+        options: {
+          temperature: 0,
+          num_predict: 8,
+        },
+      }),
+    })
+
+    if (!response.ok) {
+      const responseBody = await response.text().catch(() => '')
+      const detailSuffix = compactDetail(responseBody)
+      return {
+        state: 'generation_failed',
+        models,
+        probeModel,
+        detail: detailSuffix
+          ? `status ${response.status}: ${detailSuffix}`
+          : `status ${response.status}`,
+      }
+    }
+
+    try {
+      await response.json()
+    } catch {
+      return {
+        state: 'generation_failed',
+        models,
+        probeModel,
+        detail: 'invalid JSON response',
+      }
+    }
+
+    return {
+      state: 'ready',
+      models,
+      probeModel,
+    }
+  } catch (error) {
+    const detail =
+      error instanceof Error
+        ? error.name === 'AbortError'
+          ? 'request timed out'
+          : error.message
+        : String(error)
+
+    return {
+      state: 'generation_failed',
+      models,
+      probeModel,
+      detail,
+    }
+  } finally {
+    clear()
+  }
+}
diff --git a/src/utils/settings/settings.ts b/src/utils/settings/settings.ts
index 6d3da9ae..a10a6e71 100644
--- a/src/utils/settings/settings.ts
+++ b/src/utils/settings/settings.ts
@@ -300,9 +300,9 @@ export function getRelativeSettingsFilePathForSource(
 ): string {
   switch (source) {
     case 'projectSettings':
-      return join('.openclaude', 'settings.json')
+      return '.openclaude/settings.json'
     case 'localSettings':
-      return join('.openclaude', 'settings.local.json')
+      return '.openclaude/settings.local.json'
   }
 }
 
diff --git a/src/utils/urlRedaction.test.ts b/src/utils/urlRedaction.test.ts
new file mode 100644
index 00000000..17ccd5df
--- /dev/null
+++ b/src/utils/urlRedaction.test.ts
@@ -0,0 +1,38 @@
+import { describe, expect, test } from 'bun:test'
+
+import { redactUrlForDisplay } from './urlRedaction.ts'
+
+describe('redactUrlForDisplay', () => {
+  test('redacts credentials and sensitive query params for valid URLs', () => {
+    const redacted = redactUrlForDisplay(
+      'http://user:pass@localhost:11434/v1?api_key=secret&foo=bar',
+    )
+
+    expect(redacted).toBe(
+      'http://redacted:redacted@localhost:11434/v1?api_key=redacted&foo=bar',
+    )
+  })
+
+  test('redacts token-like query parameter names', () => {
+    const redacted = redactUrlForDisplay(
+      'https://example.com/v1?x_access_token=abc123&model=qwen2.5-coder',
+    )
+
+    expect(redacted).toBe(
+      'https://example.com/v1?x_access_token=redacted&model=qwen2.5-coder',
+    )
+  })
+
+  test('falls back to regex redaction for malformed URLs', () => {
+    const redacted = redactUrlForDisplay(
+      '//user:pass@localhost:11434?token=abc&mode=test',
+    )
+
+    expect(redacted).toBe('//redacted@localhost:11434?token=redacted&mode=test')
+  })
+
+  test('keeps non-sensitive URLs unchanged', () => {
+    const url = 'http://localhost:11434/v1?model=llama3.1:8b'
+    expect(redactUrlForDisplay(url)).toBe(url)
+  })
+})
\ No newline at end of file
diff --git a/src/utils/urlRedaction.ts b/src/utils/urlRedaction.ts
new file mode 100644
index 00000000..64eefabd
--- /dev/null
+++ b/src/utils/urlRedaction.ts
@@ -0,0 +1,48 @@
+const SENSITIVE_URL_QUERY_PARAM_TOKENS = [
+  'api_key',
+  'apikey',
+  'key',
+  'token',
+  'access_token',
+  'refresh_token',
+  'signature',
+  'sig',
+  'secret',
+  'password',
+  'passwd',
+  'pwd',
+  'auth',
+  'authorization',
+]
+
+function shouldRedactUrlQueryParam(name: string): boolean {
+  const lower = name.toLowerCase()
+  return SENSITIVE_URL_QUERY_PARAM_TOKENS.some(token => lower.includes(token))
+}
+
+export function redactUrlForDisplay(rawUrl: string): string {
+  try {
+    const parsed = new URL(rawUrl)
+    if (parsed.username) {
+      parsed.username = 'redacted'
+    }
+    if (parsed.password) {
+      parsed.password = 'redacted'
+    }
+
+    for (const key of parsed.searchParams.keys()) {
+      if (shouldRedactUrlQueryParam(key)) {
+        parsed.searchParams.set(key, 'redacted')
+      }
+    }
+
+    return parsed.toString()
+  } catch {
+    return rawUrl
+      .replace(/\/\/[^/@\s]+(?::[^/@\s]*)?@/g, '//redacted@')
+      .replace(
+        /([?&](?:token|access_token|refresh_token|api_key|apikey|key|password|passwd|pwd|auth|authorization|signature|sig|secret)=)[^&#]*/gi,
+        '$1redacted',
+      )
+  }
+}
\ No newline at end of file