diff --git a/.github/workflows/e2e-v2.yml b/.github/workflows/e2e-v2.yml
index b599dba896..0abaee3d32 100644
--- a/.github/workflows/e2e-v2.yml
+++ b/.github/workflows/e2e-v2.yml
@@ -428,12 +428,28 @@ jobs:
         with:
           model: ${{ env.IOS_DEVICE }}
           os_version: ${{ env.IOS_VERSION }}
+          # Cirrus Labs Tart VMs need more time to fully boot the simulator before
+          # Maestro can connect; without this the boot races with driver startup.
+          wait_for_boot: true
+          # Skip erasing the simulator before boot — each Maestro flow already
+          # reinstalls the app via clearState, and the erase adds overhead that
+          # makes the simulator less stable on nested-virtualisation Tart VMs.
+          erase_before_boot: false
+
+      - name: Warm up iOS simulator
+        if: ${{ matrix.platform == 'ios' }}
+        run: |
+          # Tart VMs are very slow right after boot.  Launch a stock app so
+          # that SpringBoard, backboardd, and other system services finish
+          # their post-boot initialisation before Maestro tries to connect.
+          xcrun simctl launch booted com.apple.Preferences || true
+          sleep 5
+          xcrun simctl terminate booted com.apple.Preferences || true
 
       - name: Run tests on iOS
         if: ${{ matrix.platform == 'ios' }}
         env:
-          # Increase timeout for Maestro iOS driver startup (default is 60s, some CI runners need more time)
-          MAESTRO_DRIVER_STARTUP_TIMEOUT: 120000
+          MAESTRO_DRIVER_STARTUP_TIMEOUT: 180000
         run: ./dev-packages/e2e-tests/cli.mjs ${{ matrix.platform }} --test
 
       - name: Upload logs
diff --git a/dev-packages/e2e-tests/cli.mjs b/dev-packages/e2e-tests/cli.mjs
index fded8479b3..da6ca500e2 100755
--- a/dev-packages/e2e-tests/cli.mjs
+++ b/dev-packages/e2e-tests/cli.mjs
@@ -290,20 +290,50 @@ if (actions.includes('test')) {
   if (!sentryAuthToken) {
     console.log('Skipping maestro test due to unavailable or empty SENTRY_AUTH_TOKEN');
   } else {
+    const maxAttempts = 3;
+    const maestroDir = path.join(e2eDir, 'maestro');
+    const flowFiles = fs.readdirSync(maestroDir)
+      .filter(f => f.endsWith('.yml') && !fs.statSync(path.join(maestroDir, f)).isDirectory())
+      .sort();
+
+    console.log(`Found ${flowFiles.length} test flows: ${flowFiles.join(', ')}`);
+
+    const results = [];
+
     try {
-      execSync(
-        `maestro test maestro \
-          --env=APP_ID="${appId}" \
-          --env=SENTRY_AUTH_TOKEN="${sentryAuthToken}" \
-          --debug-output maestro-logs \
-          --flatten-debug-output`,
-        {
-          stdio: 'inherit',
-          cwd: e2eDir,
-        },
-      );
+      for (const flowFile of flowFiles) {
+        const flowName = flowFile.replace('.yml', '');
+        let passed = false;
+
+        for (let attempt = 1; attempt <= maxAttempts; attempt++) {
+          const label = `[${flowName}] Attempt ${attempt}/${maxAttempts}`;
+          console.log(`\n${'='.repeat(60)}\n${label}\n${'='.repeat(60)}`);
+          try {
+            execFileSync('maestro', [
+              'test', `maestro/${flowFile}`,
+              '--env', `APP_ID=${appId}`,
+              '--env', `SENTRY_AUTH_TOKEN=${sentryAuthToken}`,
+              '--debug-output', 'maestro-logs',
+              '--flatten-debug-output',
+            ], {
+              stdio: 'inherit',
+              cwd: e2eDir,
+            });
+            console.log(`${label} — PASSED`);
+            passed = true;
+            break;
+          } catch (error) {
+            console.error(`${label} — FAILED`);
+            if (attempt < maxAttempts) {
+              console.log(`Retrying ${flowName}…`);
+            }
+          }
+        }
+
+        results.push({ flowName, passed });
+      }
     } finally {
-      // Always redact sensitive data, even if the test fails
+      // Always redact sensitive data, even if a test fails
       const redactScript = `
         if [[ "$(uname)" == "Darwin" ]]; then
           find ./maestro-logs -type f -exec sed -i '' "s/${sentryAuthToken}/[REDACTED]/g" {} +
@@ -320,5 +350,20 @@ if (actions.includes('test')) {
         console.warn('Failed to redact sensitive data from logs:', error.message);
       }
     }
+
+    // Print summary
+    console.log(`\n${'='.repeat(60)}\nTest Summary\n${'='.repeat(60)}`);
+    const failed = [];
+    for (const { flowName, passed } of results) {
+      const icon = passed ? 'PASS' : 'FAIL';
+      console.log(`  ${icon}  ${flowName}`);
+      if (!passed) failed.push(flowName);
+    }
+
+    if (failed.length > 0) {
+      console.error(`\n${failed.length}/${results.length} flows failed after ${maxAttempts} attempts: ${failed.join(', ')}`);
+      process.exit(1);
+    }
+    console.log(`\nAll ${results.length} flows passed.`);
   }
 }
diff --git a/dev-packages/e2e-tests/maestro/crash.yml b/dev-packages/e2e-tests/maestro/crash.yml
index 4a2c41675f..2cab0ff2d2 100644
--- a/dev-packages/e2e-tests/maestro/crash.yml
+++ b/dev-packages/e2e-tests/maestro/crash.yml
@@ -4,6 +4,11 @@ jsEngine: graaljs
 - runFlow: utils/launchTestAppClear.yml
 - tapOn: "Crash"
 
-- launchApp
+# Use clearState to reinstall the app after the intentional crash.
+# Without clearState, Sentry reads the pending crash report on relaunch and
+# crashes immediately (~82ms), which then triggers iOS crash-loop protection
+# and causes the next test in the suite to also fail.
+- launchApp:
+    clearState: true
 
 - runFlow: utils/assertTestReady.yml