diff --git a/web/packages/shared/components/DesktopSession/DesktopSession.story.tsx b/web/packages/shared/components/DesktopSession/DesktopSession.story.tsx
index 4259fde7fbf56..4fef60b3badc6 100644
--- a/web/packages/shared/components/DesktopSession/DesktopSession.story.tsx
+++ b/web/packages/shared/components/DesktopSession/DesktopSession.story.tsx
@@ -30,6 +30,7 @@ import {
   TdpClient,
   TdpClientEvent,
 } from 'shared/libs/tdp';
+import { TdpError as RemoteTdpError } from 'shared/libs/tdp/client';
 
 import { DesktopSession, DesktopSessionProps } from './DesktopSession';
 
@@ -86,7 +87,15 @@ export const FetchError = () => (
 export const TdpError = () => {
   const client = fakeClient();
   client.connect = async () => {
-    client.emit(TdpClientEvent.ERROR, new Error('some tdp error'));
+    client.emit(
+      TdpClientEvent.ERROR,
+      new RemoteTdpError(
+        'RDP client exited with an error: Connection Timed Out.\n\n' +
+          'Teleport could not connect to the host within the timeout period. This may be due to a firewall blocking the connection, an overloaded system, or network congestion.\n\n' +
+          'To resolve this issue, ensure that the Teleport agent can reach the Windows host.\n\n' +
+          'You can use the command "nc -vz HOST 3389" to help diagnose connectivity problems.'
+      )
+    );
   };
 
   return <DesktopSession {...props} client={client} />;
@@ -96,10 +105,10 @@ export const Connected = () => {
   return <DesktopSession {...props} />;
 };
 
-export const Disconnected = () => {
+export const DisconnectedWithNoMessage = () => {
   const client = fakeClient();
   client.connect = async () => {
-    client.emit(TdpClientEvent.TRANSPORT_CLOSE, 'session disconnected');
+    client.emit(TdpClientEvent.TRANSPORT_CLOSE);
   };
 
   return <DesktopSession {...props} client={client} />;
diff --git a/web/packages/shared/components/DesktopSession/DesktopSession.tsx b/web/packages/shared/components/DesktopSession/DesktopSession.tsx
index fd24992c90f4f..278c5e38ff1d2 100644
--- a/web/packages/shared/components/DesktopSession/DesktopSession.tsx
+++ b/web/packages/shared/components/DesktopSession/DesktopSession.tsx
@@ -37,6 +37,7 @@ import {
   TdpClient,
   useListener,
 } from 'shared/libs/tdp';
+import { TdpError } from 'shared/libs/tdp/client';
 
 import { KeyboardHandler } from './KeyboardHandler';
 import TopBar from './TopBar';
@@ -130,7 +131,8 @@ export function DesktopSession({
       setClipboardSharingState(defaultClipboardSharingState);
       setTdpConnectionStatus({
         status: 'disconnected',
-        message: error.message || error.toString(),
+        fromTdpError: error instanceof TdpError,
+        message: error?.message || error?.toString(),
       });
       initialTdpConnectionSucceeded.current = false;
     },
@@ -166,8 +168,11 @@ export function DesktopSession({
   useListener(
     client.onTransportClose,
     useCallback(
-      statusText => {
-        setTdpConnectionStatus({ status: 'disconnected', message: statusText });
+      error => {
+        setTdpConnectionStatus({
+          status: 'disconnected',
+          message: error?.message || error?.toString(),
+        });
         initialTdpConnectionSucceeded.current = false;
       },
       [setTdpConnectionStatus]
@@ -350,7 +355,7 @@ export function DesktopSession({
         />
       )}
       {screenState.state === 'custom' && screenState.component}
-      {screenState.state === 'error' && (
+      {screenState.state === 'disconnected' && (
         <AlertDialog message={screenState.message} onRetry={onRetry} />
       )}
       {screenState.state === 'processing' && <Processing />}
@@ -447,7 +452,7 @@ function getScreenState(
 
   if (aclAttempt.status === 'error') {
     return {
-      state: 'error',
+      state: 'disconnected',
       message: {
         title: 'Could not fetch session details',
         details: aclAttempt.statusText,
@@ -456,7 +461,7 @@ function getScreenState(
   }
   if (anotherDesktopActiveAttempt.status === 'error') {
     return {
-      state: 'error',
+      state: 'disconnected',
       message: {
         title: 'Could not fetch session details',
         details: anotherDesktopActiveAttempt.statusText,
@@ -465,8 +470,8 @@ function getScreenState(
   }
   if (tdpConnectionStatus.status === 'disconnected') {
     return {
-      state: 'error',
-      message: { title: tdpConnectionStatus.message },
+      state: 'disconnected',
+      message: { title: tdpConnectionStatus.message || 'Session disconnected' },
     };
   }
 
@@ -499,6 +504,7 @@ type TdpConnectionStatus =
    */
   | {
       status: 'disconnected';
+      fromTdpError?: boolean;
       message: string;
     };
 
@@ -508,6 +514,11 @@ type ScreenState =
   | { state: 'processing' }
   | { state: 'canvas-visible' }
   | {
-      state: 'error';
-      message: { title: string; details?: string };
+      state: 'disconnected';
+      message: DisconnectedMessage;
     };
+
+interface DisconnectedMessage {
+  title: string;
+  details?: string;
+}
diff --git a/web/packages/shared/libs/tdp/client.ts b/web/packages/shared/libs/tdp/client.ts
index 122e91ffa40af..fe694939c0154 100644
--- a/web/packages/shared/libs/tdp/client.ts
+++ b/web/packages/shared/libs/tdp/client.ts
@@ -144,7 +144,7 @@ export class TdpClient extends EventEmitter {
         this.transportAbortController.signal
       );
     } catch (error) {
-      this.emit(TdpClientEvent.ERROR, error.message);
+      this.emit(TdpClientEvent.ERROR, error);
       return;
     }
 
@@ -183,11 +183,11 @@ export class TdpClient extends EventEmitter {
 
     // 'Processing' errors are the most important.
     if (processingError) {
-      this.emit(TdpClientEvent.ERROR, processingError.message);
+      this.emit(TdpClientEvent.ERROR, processingError);
     } else if (connectionError) {
-      this.emit(TdpClientEvent.TRANSPORT_CLOSE, connectionError.message);
+      this.emit(TdpClientEvent.TRANSPORT_CLOSE, connectionError);
     } else {
-      this.emit(TdpClientEvent.TRANSPORT_CLOSE, 'Session disconnected');
+      this.emit(TdpClientEvent.TRANSPORT_CLOSE);
     }
 
     this.logger.info('Transport is closed');
@@ -235,7 +235,7 @@ export class TdpClient extends EventEmitter {
     return () => this.off(TdpClientEvent.TDP_WARNING, listener);
   };
 
-  onTransportClose = (listener: (message: string) => void) => {
+  onTransportClose = (listener: (error?: Error) => void) => {
     this.on(TdpClientEvent.TRANSPORT_CLOSE, listener);
     return () => this.off(TdpClientEvent.TRANSPORT_CLOSE, listener);
   };
@@ -391,7 +391,7 @@ export class TdpClient extends EventEmitter {
   handleTdpNotification(buffer: ArrayBuffer) {
     const notification = this.codec.decodeNotification(buffer);
     if (notification.severity === Severity.Error) {
-      throw new Error(notification.message);
+      throw new TdpError(notification.message);
     } else if (notification.severity === Severity.Warning) {
       this.handleWarning(notification.message, TdpClientEvent.TDP_WARNING);
     } else {
@@ -799,3 +799,11 @@ export function useListener<T extends any[]>(
     };
   }, [emitter, listener]);
 }
+
+/** Represents an alert emitted by the TDP service with "error" severity. */
+export class TdpError extends Error {
+  constructor(message: string) {
+    super(message);
+    this.name = 'TdpError';
+  }
+}
diff --git a/web/packages/teleport/src/lib/tdp/webSocketTransportAdapter.ts b/web/packages/teleport/src/lib/tdp/webSocketTransportAdapter.ts
index 0eed87426a0ad..92c8c153f4aca 100644
--- a/web/packages/teleport/src/lib/tdp/webSocketTransportAdapter.ts
+++ b/web/packages/teleport/src/lib/tdp/webSocketTransportAdapter.ts
@@ -30,6 +30,9 @@ export async function adaptWebSocketToTdpTransport(
   socket: WebSocket,
   signal: AbortSignal
 ): Promise<TdpTransport> {
+  if (signal.aborted) {
+    throw new DOMException('Websocket was aborted.', 'AbortError');
+  }
   // WebsocketCloseCode.NORMAL
   signal.addEventListener('abort', () => socket.close(1000));
   socket.binaryType = 'arraybuffer';