diff --git a/lib/services_gae.dart b/lib/services_gae.dart
index cfe4aaa..90692bd 100644
--- a/lib/services_gae.dart
+++ b/lib/services_gae.dart
@@ -117,7 +117,7 @@
   }
 
   Future _processReadynessRequest(io.HttpRequest request) async {
-    if (commonServerImpl.running) {
+    if (!commonServerImpl.isRestarting) {
       request.response.statusCode = io.HttpStatus.ok;
     } else {
       request.response.statusCode = io.HttpStatus.internalServerError;
@@ -128,9 +128,9 @@
   }
 
   Future _processHealthRequest(io.HttpRequest request) async {
-    if (commonServerImpl.running && !commonServerImpl.analysisServersRunning) {
-      _logger.severe('CommonServer running without analysis servers. '
-          'Intentionally failing healthcheck.');
+    if (!commonServerImpl.isHealthy) {
+      _logger.severe('CommonServer is no longer healthy.'
+          ' Intentionally failing health check.');
       request.response.statusCode = io.HttpStatus.internalServerError;
     } else {
       try {
@@ -140,15 +140,20 @@
           await file.writeAsString('testing123\n' * 1000, flush: true);
           final stat = await file.stat();
           if (stat.size > 10000) {
+            _logger.info('CommonServer healthy and file system working.'
+                ' Passing health check.');
             request.response.statusCode = io.HttpStatus.ok;
           } else {
+            _logger.severe('CommonServer healthy, but filesystem is not.'
+                ' Intentionally failing health check.');
             request.response.statusCode = io.HttpStatus.internalServerError;
           }
         } finally {
           await tempDir.delete(recursive: true);
         }
       } catch (e) {
-        _logger.severe('Failed to create temporary file: $e');
+        _logger.severe('CommonServer healthy, but failed to create temporary'
+            ' file: $e');
         request.response.statusCode = io.HttpStatus.internalServerError;
       }
     }
diff --git a/lib/src/common_server_impl.dart b/lib/src/common_server_impl.dart
index 4030ffa..5f13521 100644
--- a/lib/src/common_server_impl.dart
+++ b/lib/src/common_server_impl.dart
@@ -27,6 +27,7 @@
 
 class BadRequest implements Exception {
   String cause;
+
   BadRequest(this.cause);
 }
 
@@ -48,8 +49,17 @@
       analysisServer.analysisServer != null &&
       flutterAnalysisServer.analysisServer != null;
 
-  bool _running = false;
-  bool get running => _running;
+  // If non-null, this value indicates that the server is starting/restarting
+  // and holds the time at which that process began. If null, the server is
+  // ready to handle requests.
+  DateTime _restartingSince = DateTime.now();
+
+  bool get isRestarting => (_restartingSince != null);
+
+  // If the server has been trying and failing to restart for more than a half
+  // hour, something is seriously wrong.
+  bool get isHealthy => (_restartingSince == null ||
+      DateTime.now().difference(_restartingSince).inMinutes < 30);
 
   CommonServerImpl(
     this.sdkPath,
@@ -90,7 +100,7 @@
       }
     }));
 
-    _running = true;
+    _restartingSince = null;
   }
 
   Future<void> warmup({bool useHtml = false}) async {
@@ -112,7 +122,8 @@
   }
 
   Future<dynamic> shutdown() {
-    _running = false;
+    _restartingSince = DateTime.now();
+
     return Future.wait(<Future<dynamic>>[
       analysisServer.shutdown(),
       flutterAnalysisServer.shutdown(),