diff --git a/pkgs/dart_mcp_server/CHANGELOG.md b/pkgs/dart_mcp_server/CHANGELOG.md
index 83c27103..32429e8d 100644
--- a/pkgs/dart_mcp_server/CHANGELOG.md
+++ b/pkgs/dart_mcp_server/CHANGELOG.md
@@ -40,3 +40,4 @@
 * Instruct clients to prefer MCP tools over running tools in the shell.
 * Reduce output size of `run_tests` tool to save on input tokens.
 * Add `--log-file` argument to log all protocol traffic to a file.
+* Improve error text for failed DTD connections as well as the tool description.
diff --git a/pkgs/dart_mcp_server/lib/src/mixins/dtd.dart b/pkgs/dart_mcp_server/lib/src/mixins/dtd.dart
index 1dfffe44..6d585910 100644
--- a/pkgs/dart_mcp_server/lib/src/mixins/dtd.dart
+++ b/pkgs/dart_mcp_server/lib/src/mixins/dtd.dart
@@ -12,6 +12,7 @@ import 'package:json_rpc_2/json_rpc_2.dart';
 import 'package:meta/meta.dart';
 import 'package:vm_service/vm_service.dart';
 import 'package:vm_service/vm_service_io.dart';
+import 'package:web_socket/web_socket.dart';
 
 import '../utils/constants.dart';
 
@@ -182,10 +183,19 @@ base mixin DartToolingDaemonSupport
       return CallToolResult(
         content: [TextContent(text: 'Connection succeeded')],
       );
+    } on WebSocketException catch (_) {
+      return CallToolResult(
+        isError: true,
+        content: [
+          Content.text(
+            text: 'Connection failed, make sure your DTD Uri is up to date.',
+          ),
+        ],
+      );
     } catch (e) {
       return CallToolResult(
         isError: true,
-        content: [TextContent(text: 'Connection failed: $e')],
+        content: [Content.text(text: 'Connection failed: $e')],
       );
     }
   }
@@ -602,9 +612,11 @@ base mixin DartToolingDaemonSupport
   static final connectTool = Tool(
     name: 'connect_dart_tooling_daemon',
     description:
-        'Connects to the Dart Tooling Daemon. You should ask the user for the '
-        'dart tooling daemon URI, and suggest the "Copy DTD Uri to clipboard" '
-        'command. Do not just make up a random URI to pass.',
+        'Connects to the Dart Tooling Daemon. You should get the uri either '
+        'from available tools or the user, do not just make up a random URI to '
+        'pass. When asking the user for the uri, you should suggest the "Copy '
+        'DTD Uri to clipboard" action. Do . When reconnecting after losing a '
+        'connection, always request a new uri first.',
     annotations: ToolAnnotations(title: 'Connect to DTD', readOnlyHint: true),
     inputSchema: Schema.object(
       properties: {ParameterNames.uri: Schema.string()},
diff --git a/pkgs/dart_mcp_server/pubspec.yaml b/pkgs/dart_mcp_server/pubspec.yaml
index b560d110..03e1aea4 100644
--- a/pkgs/dart_mcp_server/pubspec.yaml
+++ b/pkgs/dart_mcp_server/pubspec.yaml
@@ -35,6 +35,7 @@ dependencies:
   stream_channel: ^2.1.4
   vm_service: ^15.0.0
   watcher: ^1.1.1
+  web_socket: ^1.0.1
   yaml: ^3.1.3
 
 dev_dependencies: