diff --git a/packages/cli/src/commands/pw-test.ts b/packages/cli/src/commands/pw-test.ts
index 36481dee..b0514ecb 100644
--- a/packages/cli/src/commands/pw-test.ts
+++ b/packages/cli/src/commands/pw-test.ts
@@ -21,6 +21,7 @@ import {
   Events,
   MAX_SCHEDULING_DELAY_SECONDS,
   SequenceId,
+  CheckFailure,
 } from '../services/abstract-check-runner.js'
 import { TestResultsShortLinks } from '../rest/test-sessions.js'
 import commonMessages from '../messages/common-messages.js'
@@ -361,13 +362,14 @@ export default class PwTestCommand extends AuthCommand {
         }, testResultId, links))
       })
 
-    runner.on(Events.CHECK_FAILED, (sequenceId: SequenceId, check, message: string) => {
+    runner.on(Events.CHECK_FAILED, (sequenceId: SequenceId, check, message: string, failure?: CheckFailure) => {
       reporters.forEach(r => r.onCheckEnd(sequenceId, {
         ...check,
         logicalId: check.logicalId,
         sourceFile: check.getSourceFile(),
         hasFailures: true,
         runError: message,
+        timedOut: failure?.timedOut ?? false,
       }))
       if (message.includes('No tests found')) {
         this.style.shortInfo('Check your Playwright configuration to ensure it targets your test files.')
diff --git a/packages/cli/src/commands/test.ts b/packages/cli/src/commands/test.ts
index efbd69e6..e6847ab9 100644
--- a/packages/cli/src/commands/test.ts
+++ b/packages/cli/src/commands/test.ts
@@ -6,6 +6,7 @@ import { parseProject } from '../services/project-parser.js'
 import {
   Events,
   SequenceId,
+  CheckFailure,
   DEFAULT_CHECK_RUN_TIMEOUT_SECONDS,
   MAX_SCHEDULING_DELAY_SECONDS,
 } from '../services/abstract-check-runner.js'
@@ -433,13 +434,14 @@ export default class Test extends AuthCommand {
         }, testResultId, links))
       })
 
-    runner.on(Events.CHECK_FAILED, (sequenceId: SequenceId, check, message: string) => {
+    runner.on(Events.CHECK_FAILED, (sequenceId: SequenceId, check, message: string, failure?: CheckFailure) => {
       reporters.forEach(r => r.onCheckEnd(sequenceId, {
         ...check,
         logicalId: check.logicalId,
         sourceFile: check.getSourceFile(),
         hasFailures: true,
         runError: message,
+        timedOut: failure?.timedOut ?? false,
       }))
       process.exitCode = 1
     })
diff --git a/packages/cli/src/commands/trigger.ts b/packages/cli/src/commands/trigger.ts
index f811f44e..7e7b7bed 100644
--- a/packages/cli/src/commands/trigger.ts
+++ b/packages/cli/src/commands/trigger.ts
@@ -12,6 +12,7 @@ import {
   Events,
   PrivateRunLocation,
   SequenceId,
+  CheckFailure,
   DEFAULT_CHECK_RUN_TIMEOUT_SECONDS,
   MAX_SCHEDULING_DELAY_SECONDS,
 } from '../services/abstract-check-runner.js'
@@ -210,11 +211,12 @@ export default class Trigger extends AuthCommand {
         }
         reporters.forEach(r => r.onCheckEnd(sequenceId, result, testResultId, links))
       })
-    runner.on(Events.CHECK_FAILED, (sequenceId: SequenceId, check, message: string) => {
+    runner.on(Events.CHECK_FAILED, (sequenceId: SequenceId, check, message: string, failure?: CheckFailure) => {
       reporters.forEach(r => r.onCheckEnd(sequenceId, {
         ...check,
         hasFailures: true,
         runError: message,
+        timedOut: failure?.timedOut ?? false,
       }))
       process.exitCode = 1
     })
diff --git a/packages/cli/src/reporters/__tests__/abstract-list.spec.ts b/packages/cli/src/reporters/__tests__/abstract-list.spec.ts
index e67cb5b3..85881b2d 100644
--- a/packages/cli/src/reporters/__tests__/abstract-list.spec.ts
+++ b/packages/cli/src/reporters/__tests__/abstract-list.spec.ts
@@ -312,6 +312,28 @@ describe('AbstractListReporter', () => {
     expect(countOccurrences(output, `Open session: ${TEST_SESSION_URL}`)).toBe(1)
   })
 
+  it('counts and titles a check the CLI stopped waiting for as timed out, not failed', () => {
+    withTty(process.stdout, false, () => {
+      const reporter = new ListReporter(PUBLIC_RUN_LOCATION, false)
+      const slow = { name: 'Slow Check', getSourceFile: () => SOURCE_FILE }
+      const broken = { name: 'Broken Check', getSourceFile: () => SOURCE_FILE }
+      reporter.onBegin([
+        { check: slow, sequenceId: 'seq-slow' },
+        { check: broken, sequenceId: 'seq-broken' },
+      ])
+      reporter.onCheckEnd('seq-slow', {
+        ...makePassingResult(), name: 'Slow Check', hasFailures: true, runError: 'Reached timeout', timedOut: true,
+      })
+      reporter.onCheckEnd('seq-broken', { ...makePassingResult(), name: 'Broken Check', hasFailures: true })
+      printLnMock.mockClear()
+      reporter._printSummary()
+
+      const summary = outputOf(printLnMock)
+      expect(summary).toContain('⏱ Slow Check')
+      expect(summary).toContain('1 failed, 1 timed out, 2 total')
+    })
+  })
+
   describe('after the run stopped at the max failures limit', () => {
     function makeStoppedReporter (
       reporter = new ListReporter(PUBLIC_RUN_LOCATION, false),
diff --git a/packages/cli/src/reporters/__tests__/dot.spec.ts b/packages/cli/src/reporters/__tests__/dot.spec.ts
index a62bccca..df0f1e58 100644
--- a/packages/cli/src/reporters/__tests__/dot.spec.ts
+++ b/packages/cli/src/reporters/__tests__/dot.spec.ts
@@ -117,6 +117,20 @@ describe('DotReporter', () => {
     expect(output).toContain('My Playwright Check')
   })
 
+  it('marks and summarizes a check the CLI stopped waiting for as timed out', () => {
+    const { reporter } = makeReporterWithOneCheck()
+
+    reporter.onCheckEnd(SEQUENCE_ID, makeResult({ hasFailures: true, runError: RUN_ERROR, timedOut: true }))
+    reporter.onEnd()
+
+    expect(marks()).toBe('T')
+    const output = printedOutput()
+    expect(output).toContain('1 timed out, 1 total')
+    expect(output).not.toContain('failed')
+    expect(output).toContain('⏱ My Playwright Check')
+    expect(output).toContain(RUN_ERROR)
+  })
+
   it('should not print execution error details for a passing check', () => {
     const { reporter } = makeReporterWithOneCheck()
 
diff --git a/packages/cli/src/reporters/__tests__/github-md-builder.spec.ts b/packages/cli/src/reporters/__tests__/github-md-builder.spec.ts
index 4af4533e..fdf113cf 100644
--- a/packages/cli/src/reporters/__tests__/github-md-builder.spec.ts
+++ b/packages/cli/src/reporters/__tests__/github-md-builder.spec.ts
@@ -66,6 +66,28 @@ describe('GithubMdBuilder', () => {
     expect(markdown).toContain('## Execution Errors')
     expect(markdown).toContain(runError)
   })
+  test('labels a check the CLI stopped waiting for as timed out, not failed', () => {
+    const row = (name: string, timedOut: boolean) => [`seq-${name}`, {
+      result: { name, sourceFile: 'folder/timeout.check.ts', hasFailures: true, runError: 'Error', timedOut },
+      titleString: name,
+      numRetries: 1,
+    }] as const
+    const map: checkFilesMap = new Map([
+      ['folder/timeout.check.ts', new Map([
+        row('Slow check', true),
+        row('Crashed check', false),
+      ])],
+    ])
+    const markdown = new GithubMdBuilder({
+      testSessionId,
+      numChecks: 2,
+      runLocation,
+      checkFilesMap: map,
+    }).render()
+    expect(markdown).toContain('|⏱️ Timed out (1 retry)|Slow check|')
+    expect(markdown).toContain('|❌ Fail (1 retry)|Crashed check|')
+    expect(markdown).toContain('## Execution Errors')
+  })
   test('shows the retry count in the status cell of a check that needed retries', () => {
     const row = (name: string, hasFailures: boolean, numRetries: number) => [`seq-${name}`, {
       result: { name, sourceFile: 'folder/retry.check.ts', hasFailures, checkType: 'API', responseTime: 10 },
diff --git a/packages/cli/src/reporters/__tests__/json-builder.spec.ts b/packages/cli/src/reporters/__tests__/json-builder.spec.ts
index 2fa2f779..258199e4 100644
--- a/packages/cli/src/reporters/__tests__/json-builder.spec.ts
+++ b/packages/cli/src/reporters/__tests__/json-builder.spec.ts
@@ -135,6 +135,35 @@ describe('JsonBuilder', () => {
     })
   })
 
+  test('reports a check the CLI stopped waiting for as timed out', () => {
+    const runError = 'Reached timeout of 600 seconds waiting for check result.'
+    const map: checkFilesMap = new Map([
+      ['folder/timeout.check.ts', new Map([
+        ['seq-timeout', {
+          result: { name: 'Slow check', sourceFile: 'folder/timeout.check.ts', hasFailures: true, runError, timedOut: true },
+          titleString: 'Slow check',
+          numRetries: 0,
+        }],
+        ['seq-crashed', {
+          result: { name: 'Crashed check', sourceFile: 'folder/timeout.check.ts', hasFailures: true, runError: 'Error' },
+          titleString: 'Crashed check',
+          numRetries: 0,
+        }],
+      ])],
+    ])
+    const summary = JSON.parse(new JsonBuilder({
+      testSessionId: undefined,
+      numChecks: 2,
+      runLocation,
+      checkFilesMap: map,
+    }).render())
+
+    expect(summary.checks.map((c: any) => [c.name, c.result, c.runError])).toEqual([
+      ['Slow check', 'Timed out', runError],
+      ['Crashed check', 'Fail', 'Error'],
+    ])
+  })
+
   test('omits stoppedEarly when the run finished', () => {
     const checkFilesMap = generateMapAndTestResultIds({ includeTestResultIds: false })
     const summary = JSON.parse(new JsonBuilder({
diff --git a/packages/cli/src/reporters/__tests__/util.spec.ts b/packages/cli/src/reporters/__tests__/util.spec.ts
index 89091d38..27e823f8 100644
--- a/packages/cli/src/reporters/__tests__/util.spec.ts
+++ b/packages/cli/src/reporters/__tests__/util.spec.ts
@@ -237,6 +237,21 @@ describe('resultToCheckStatus()', () => {
     expect(resultToCheckStatus({ isCancelled: true, hasFailures: true }))
       .toBe(CheckStatus.CANCELLED)
   })
+  it('returns timed out for a check the CLI stopped waiting for', () => {
+    expect(resultToCheckStatus({ hasFailures: true, runError: 'Reached timeout', timedOut: true }))
+      .toBe(CheckStatus.TIMED_OUT)
+  })
+  it('returns failed for a run error that is not a timeout', () => {
+    expect(resultToCheckStatus({ hasFailures: true, runError: 'runner crashed', timedOut: false }))
+      .toBe(CheckStatus.FAILED)
+  })
+})
+
+describe('formatCheckTitle() with TIMED_OUT status', () => {
+  it('should use the ⏱ symbol for a timed-out check title', () => {
+    const result = stripAnsi(formatCheckTitle(CheckStatus.TIMED_OUT, simpleCheckFixture))
+    expect(result).toContain('⏱')
+  })
 })
 
 describe('formatCheckTitle() with CANCELLED status', () => {
diff --git a/packages/cli/src/reporters/abstract-list.ts b/packages/cli/src/reporters/abstract-list.ts
index 993fd89d..ba7b0fc8 100644
--- a/packages/cli/src/reporters/abstract-list.ts
+++ b/packages/cli/src/reporters/abstract-list.ts
@@ -230,7 +230,7 @@ export default abstract class AbstractListReporter implements Reporter {
   } = {}) {
     const write = opts.stream === 'stderr' ? printLnErr : printLn
     const counts = {
-      numFailed: 0, numPassed: 0, numDegraded: 0, numFlaky: 0,
+      numFailed: 0, numTimedOut: 0, numPassed: 0, numDegraded: 0, numFlaky: 0,
       numRunning: 0, numRetrying: 0, scheduling: 0, numCancelled: 0, numNotFinished: 0,
     }
     const status = []
@@ -249,6 +249,8 @@ export default abstract class AbstractListReporter implements Reporter {
           counts.numRetrying++
         } else if (!result) {
           counts.numRunning++
+        } else if (checkStatus === CheckStatus.TIMED_OUT) {
+          counts.numTimedOut++
         } else if (result.hasFailures) {
           counts.numFailed++
         } else if (result.isDegraded) {
@@ -302,6 +304,7 @@ export default abstract class AbstractListReporter implements Reporter {
         counts.numRunning ? chalk.bold.magenta(`${counts.numRunning} running`) : undefined,
         counts.numRetrying ? chalk.bold(`${counts.numRetrying} retrying`) : undefined,
         counts.numFailed ? chalk.bold.red(`${counts.numFailed} failed`) : undefined,
+        counts.numTimedOut ? chalk.bold.red(`${counts.numTimedOut} timed out`) : undefined,
         counts.numDegraded ? chalk.bold.yellow(`${counts.numDegraded} degraded`) : undefined,
         counts.numPassed ? chalk.bold.green(`${counts.numPassed} passed`) : undefined,
         counts.numFlaky ? chalk.bold.yellow(`${counts.numFlaky} flaky`) : undefined,
@@ -331,7 +334,9 @@ export default abstract class AbstractListReporter implements Reporter {
 
   /** `lineEnded`: the reporter already ended its last line, so no empty line opens the summary. */
   _printBriefSummary ({ lineEnded = false }: { lineEnded?: boolean } = {}) {
-    const counts = { numFailed: 0, numDegraded: 0, numPassed: 0, numPending: 0, numCancelled: 0, numNotFinished: 0 }
+    const counts = {
+      numFailed: 0, numTimedOut: 0, numDegraded: 0, numPassed: 0, numPending: 0, numCancelled: 0, numNotFinished: 0,
+    }
     const status = []
     for (const [, checkMap] of this.checkFilesMap!.entries()) {
       for (const [, { result, checkStatus }] of checkMap.entries()) {
@@ -339,6 +344,8 @@ export default abstract class AbstractListReporter implements Reporter {
           counts.numNotFinished++
         } else if (!result) {
           counts.numPending++
+        } else if (checkStatus === CheckStatus.TIMED_OUT) {
+          counts.numTimedOut++
         } else if (result.hasFailures) {
           counts.numFailed++
         } else if (result.isDegraded) {
@@ -355,6 +362,7 @@ export default abstract class AbstractListReporter implements Reporter {
     }
     status.push([
       counts.numFailed ? chalk.bold.red(`${counts.numFailed} failed`) : undefined,
+      counts.numTimedOut ? chalk.bold.red(`${counts.numTimedOut} timed out`) : undefined,
       counts.numDegraded ? chalk.bold.yellow(`${counts.numDegraded} degraded`) : undefined,
       counts.numPassed ? chalk.bold.green(`${counts.numPassed} passed`) : undefined,
       counts.numCancelled ? chalk.bold.grey(`${counts.numCancelled} cancelled`) : undefined,
@@ -379,7 +387,7 @@ export default abstract class AbstractListReporter implements Reporter {
     for (const [, checkMap] of this.checkFilesMap!.entries()) {
       for (const [, { result }] of checkMap.entries()) {
         if (result?.runError) {
-          printLn(formatCheckTitle(CheckStatus.FAILED, result))
+          printLn(formatCheckTitle(resultToCheckStatus(result), result))
           printLn(indentString(formatCheckResult(result), 4), 2, 1)
         }
       }
diff --git a/packages/cli/src/reporters/dot.ts b/packages/cli/src/reporters/dot.ts
index bd42ca90..6c034f3f 100644
--- a/packages/cli/src/reporters/dot.ts
+++ b/packages/cli/src/reporters/dot.ts
@@ -27,7 +27,9 @@ export default class DotReporter extends AbstractListReporter {
   onCheckEnd (sequenceId: SequenceId, checkResult: any) {
     super.onCheckEnd(sequenceId, checkResult)
     this.#printedMarks = true
-    if (checkResult.hasFailures) {
+    if (checkResult.timedOut) {
+      printLnErr(`${chalk.red('T')}`, 0)
+    } else if (checkResult.hasFailures) {
       printLnErr(`${chalk.red('F')}`, 0)
     } else if (checkResult.isDegraded) {
       printLnErr(`${chalk.yellow('D')}`, 0)
diff --git a/packages/cli/src/reporters/github.ts b/packages/cli/src/reporters/github.ts
index b7f59d7e..10d5fea4 100644
--- a/packages/cli/src/reporters/github.ts
+++ b/packages/cli/src/reporters/github.ts
@@ -89,7 +89,9 @@ export class GithubMdBuilder {
           continue
         }
         const checkStatus = resultToCheckStatus(result)
-        const statusCell = checkStatus === CheckStatus.FAILED ? '❌ Fail' : checkStatus === CheckStatus.DEGRADED ? '⚠️ Degraded' : '✅ Pass'
+        const statusCell = checkStatus === CheckStatus.TIMED_OUT
+          ? '⏱️ Timed out'
+          : checkStatus === CheckStatus.FAILED ? '❌ Fail' : checkStatus === CheckStatus.DEGRADED ? '⚠️ Degraded' : '✅ Pass'
         const tableRow: Array<string> = [
           `${statusCell}${retries}`,
           `${result.name}`,
diff --git a/packages/cli/src/reporters/json.ts b/packages/cli/src/reporters/json.ts
index e4fc9205..ddcbc7b4 100644
--- a/packages/cli/src/reporters/json.ts
+++ b/packages/cli/src/reporters/json.ts
@@ -121,7 +121,9 @@ export class JsonBuilder {
         }
         const checkStatus = resultToCheckStatus(result)
         const check: any = {
-          result: checkStatus === CheckStatus.FAILED ? 'Fail' : checkStatus === CheckStatus.DEGRADED ? 'Degraded' : 'Pass',
+          result: checkStatus === CheckStatus.TIMED_OUT
+            ? 'Timed out'
+            : checkStatus === CheckStatus.FAILED ? 'Fail' : checkStatus === CheckStatus.DEGRADED ? 'Degraded' : 'Pass',
           name: result.name,
           checkType: result.checkType,
           durationMilliseconds: result.responseTime ?? null,
diff --git a/packages/cli/src/reporters/list.ts b/packages/cli/src/reporters/list.ts
index 0aadba21..d048ee8f 100644
--- a/packages/cli/src/reporters/list.ts
+++ b/packages/cli/src/reporters/list.ts
@@ -64,7 +64,7 @@ export default class ListReporter extends AbstractListReporter {
       printLn(indentString(formatCheckResult(checkResult), 4), 2, 1)
     } else {
       if (checkResult.hasFailures) {
-        printLn(formatCheckTitle(CheckStatus.FAILED, checkResult))
+        printLn(formatCheckTitle(resultToCheckStatus(checkResult), checkResult))
         printLn(indentString(formatCheckResult(checkResult), 4), 2, 1)
       }
       if (checkResult.isDegraded) {
diff --git a/packages/cli/src/reporters/util.ts b/packages/cli/src/reporters/util.ts
index 3c9d346b..552c7b15 100644
--- a/packages/cli/src/reporters/util.ts
+++ b/packages/cli/src/reporters/util.ts
@@ -24,6 +24,8 @@ export enum CheckStatus {
   CANCELLED,
   // The run stopped early (max failures) before this check reported a result.
   NOT_FINISHED,
+  // The CLI stopped waiting for a result; the check may still have passed in Checkly.
+  TIMED_OUT,
 }
 
 export function formatDuration (ms: number): string {
@@ -70,6 +72,9 @@ export function formatCheckTitle (
   } else if (status === CheckStatus.NOT_FINISHED) {
     statusString = '…'
     format = chalk.bold.dim
+  } else if (status === CheckStatus.TIMED_OUT) {
+    statusString = '⏱'
+    format = chalk.bold.red
   } else {
     statusString = '-'
     format = chalk.bold.dim
@@ -776,6 +781,9 @@ export function resultToCheckStatus (checkResult: any): CheckStatus {
   if (checkResult.isCancelled) {
     return CheckStatus.CANCELLED
   }
+  if (checkResult.timedOut) {
+    return CheckStatus.TIMED_OUT
+  }
   return checkResult.hasFailures
     ? CheckStatus.FAILED
     : checkResult.isDegraded
diff --git a/packages/cli/src/services/__tests__/abstract-check-runner.spec.ts b/packages/cli/src/services/__tests__/abstract-check-runner.spec.ts
index 795d158e..74e5a2cc 100644
--- a/packages/cli/src/services/__tests__/abstract-check-runner.spec.ts
+++ b/packages/cli/src/services/__tests__/abstract-check-runner.spec.ts
@@ -747,6 +747,23 @@ describe('AbstractCheckRunner — per-check timeouts vs scheduling delay', () =>
     ;(runner as any).disableAllTimeouts()
   })
 
+  it('flags a timeout as timed out, unlike other run errors', async () => {
+    const runner = new StubCheckRunner('acc-1', TIMEOUT_SECONDS, false)
+    runner.checks = new Map([['seq-1', { check: {} }], ['seq-2', { check: {} }]])
+    const failures: Array<{ sequenceId: string, failure?: { timedOut?: boolean } }> = []
+    runner.on(Events.CHECK_FAILED, (sequenceId, _check, _message, failure) => failures.push({ sequenceId, failure }))
+    ;(runner as any).setAllTimeouts()
+
+    await (runner as any).processMessage('seq-2', 'error', 'runner crashed')
+    await vi.advanceTimersByTimeAsync((TIMEOUT_SECONDS + MAX_SCHEDULING_DELAY_SECONDS) * 1000)
+
+    expect(failures).toEqual([
+      { sequenceId: 'seq-2', failure: undefined },
+      { sequenceId: 'seq-1', failure: { timedOut: true } },
+    ])
+    ;(runner as any).disableAllTimeouts()
+  })
+
   it('a final result before the timeout produces no failure', async () => {
     const { runner, failures } = makeArmedRunner()
     const successes: string[] = []
diff --git a/packages/cli/src/services/abstract-check-runner.ts b/packages/cli/src/services/abstract-check-runner.ts
index 3e7f1948..9789306a 100644
--- a/packages/cli/src/services/abstract-check-runner.ts
+++ b/packages/cli/src/services/abstract-check-runner.ts
@@ -44,6 +44,12 @@ export type RunLocation = PublicRunLocation | PrivateRunLocation
 export type CheckRunId = string
 export type SequenceId = string
 
+// Optional details emitted with CHECK_FAILED alongside the error message.
+export type CheckFailure = {
+  // The CLI stopped waiting for a result; the check may still have passed in Checkly.
+  timedOut?: boolean
+}
+
 export const DEFAULT_CHECK_RUN_TIMEOUT_SECONDS = 600
 export const DEFAULT_PLAYWRIGHT_CHECK_RUN_TIMEOUT_SECONDS = 1200
 
@@ -493,7 +499,7 @@ export default abstract class AbstractCheckRunner extends EventEmitter {
       } else if (!started || this.timeout === DEFAULT_CHECK_RUN_TIMEOUT_SECONDS) {
         errorMessage += ' Checkly may be experiencing problems. Please check https://is.checkly.online or reach out to support@checklyhq.com.'
       }
-      this.emit(Events.CHECK_FAILED, sequenceId, check, errorMessage)
+      this.emit(Events.CHECK_FAILED, sequenceId, check, errorMessage, { timedOut: true })
       this.emit(Events.CHECK_FINISHED, check)
     }, checkTimeout * 1000))
   }