diff --git a/arduino-ide-extension/src/browser/contributions/contribution.ts b/arduino-ide-extension/src/browser/contributions/contribution.ts
index 085558a05..8de4d8ff4 100644
--- a/arduino-ide-extension/src/browser/contributions/contribution.ts
+++ b/arduino-ide-extension/src/browser/contributions/contribution.ts
@@ -68,6 +68,7 @@ import { MainMenuManager } from '../../common/main-menu-manager';
 import { ConfigServiceClient } from '../config/config-service-client';
 import { ApplicationShell } from '@theia/core/lib/browser/shell/application-shell';
 import { DialogService } from '../dialog-service';
+import { ApplicationConnectionStatusContribution } from '../theia/core/connection-status-service';
 
 export {
   Command,
@@ -172,6 +173,9 @@ export abstract class SketchContribution extends Contribution {
   @inject(EnvVariablesServer)
   protected readonly envVariableServer: EnvVariablesServer;
 
+  @inject(ApplicationConnectionStatusContribution)
+  protected readonly connectionStatusService: ApplicationConnectionStatusContribution;
+
   protected async sourceOverride(): Promise<Record<string, string>> {
     const override: Record<string, string> = {};
     const sketch = await this.sketchServiceClient.currentSketch();
diff --git a/arduino-ide-extension/src/browser/contributions/save-as-sketch.ts b/arduino-ide-extension/src/browser/contributions/save-as-sketch.ts
index 876f9c872..26dd6158f 100644
--- a/arduino-ide-extension/src/browser/contributions/save-as-sketch.ts
+++ b/arduino-ide-extension/src/browser/contributions/save-as-sketch.ts
@@ -24,6 +24,7 @@ import {
   RenameCloudSketch,
   RenameCloudSketchParams,
 } from './rename-cloud-sketch';
+import { assertConnectedToBackend } from './save-sketch';
 
 @injectable()
 export class SaveAsSketch extends CloudSketchContribution {
@@ -64,6 +65,10 @@ export class SaveAsSketch extends CloudSketchContribution {
       markAsRecentlyOpened,
     }: SaveAsSketch.Options = SaveAsSketch.Options.DEFAULT
   ): Promise<boolean> {
+    assertConnectedToBackend({
+      connectionStatusService: this.connectionStatusService,
+      messageService: this.messageService,
+    });
     const sketch = await this.sketchServiceClient.currentSketch();
     if (!CurrentSketch.isValid(sketch)) {
       return false;
diff --git a/arduino-ide-extension/src/browser/contributions/save-sketch.ts b/arduino-ide-extension/src/browser/contributions/save-sketch.ts
index d05a47982..ac20d8aa6 100644
--- a/arduino-ide-extension/src/browser/contributions/save-sketch.ts
+++ b/arduino-ide-extension/src/browser/contributions/save-sketch.ts
@@ -1,16 +1,18 @@
-import { injectable } from '@theia/core/shared/inversify';
 import { CommonCommands } from '@theia/core/lib/browser/common-frontend-contribution';
+import { MessageService } from '@theia/core/lib/common/message-service';
+import { nls } from '@theia/core/lib/common/nls';
+import { injectable } from '@theia/core/shared/inversify';
 import { ArduinoMenus } from '../menu/arduino-menus';
-import { SaveAsSketch } from './save-as-sketch';
+import { CurrentSketch } from '../sketches-service-client-impl';
+import { ApplicationConnectionStatusContribution } from '../theia/core/connection-status-service';
 import {
-  SketchContribution,
   Command,
   CommandRegistry,
-  MenuModelRegistry,
   KeybindingRegistry,
+  MenuModelRegistry,
+  SketchContribution,
 } from './contribution';
-import { nls } from '@theia/core/lib/common';
-import { CurrentSketch } from '../sketches-service-client-impl';
+import { SaveAsSketch } from './save-as-sketch';
 
 @injectable()
 export class SaveSketch extends SketchContribution {
@@ -36,6 +38,10 @@ export class SaveSketch extends SketchContribution {
   }
 
   async saveSketch(): Promise<void> {
+    assertConnectedToBackend({
+      connectionStatusService: this.connectionStatusService,
+      messageService: this.messageService,
+    });
     const sketch = await this.sketchServiceClient.currentSketch();
     if (!CurrentSketch.isValid(sketch)) {
       return;
@@ -63,3 +69,18 @@ export namespace SaveSketch {
     };
   }
 }
+
+// https://github.com/arduino/arduino-ide/issues/2081
+export function assertConnectedToBackend(param: {
+  connectionStatusService: ApplicationConnectionStatusContribution;
+  messageService: MessageService;
+}): void {
+  if (param.connectionStatusService.offlineStatus === 'backend') {
+    const message = nls.localize(
+      'theia/core/couldNotSave',
+      'Could not save the sketch. Please copy your unsaved work into your favorite text editor, and restart the IDE.'
+    );
+    param.messageService.error(message);
+    throw new Error(message);
+  }
+}
diff --git a/arduino-ide-extension/src/browser/theia/core/connection-status-service.ts b/arduino-ide-extension/src/browser/theia/core/connection-status-service.ts
index 983850d0c..b38f8d084 100644
--- a/arduino-ide-extension/src/browser/theia/core/connection-status-service.ts
+++ b/arduino-ide-extension/src/browser/theia/core/connection-status-service.ts
@@ -4,6 +4,7 @@ import {
   FrontendConnectionStatusService as TheiaFrontendConnectionStatusService,
 } from '@theia/core/lib/browser/connection-status-service';
 import type { FrontendApplicationContribution } from '@theia/core/lib/browser/frontend-application';
+import { WebSocketConnectionProvider } from '@theia/core/lib/browser/index';
 import { StatusBarAlignment } from '@theia/core/lib/browser/status-bar/status-bar';
 import { Disposable } from '@theia/core/lib/common/disposable';
 import { Emitter, Event } from '@theia/core/lib/common/event';
@@ -16,11 +17,11 @@ import {
   postConstruct,
 } from '@theia/core/shared/inversify';
 import { NotificationManager } from '@theia/messages/lib/browser/notifications-manager';
+import debounce from 'lodash.debounce';
 import { ArduinoDaemon } from '../../../common/protocol';
 import { assertUnreachable } from '../../../common/utils';
 import { CreateFeatures } from '../../create/create-features';
 import { NotificationCenter } from '../../notification-center';
-import debounce from 'lodash.debounce';
 
 @injectable()
 export class IsOnline implements FrontendApplicationContribution {
@@ -113,6 +114,8 @@ export class FrontendConnectionStatusService extends TheiaFrontendConnectionStat
   private readonly daemonPort: DaemonPort;
   @inject(IsOnline)
   private readonly isOnline: IsOnline;
+  @inject(WebSocketConnectionProvider)
+  private readonly connectionProvider: WebSocketConnectionProvider;
 
   @postConstruct()
   protected override async init(): Promise<void> {
@@ -125,6 +128,10 @@ export class FrontendConnectionStatusService extends TheiaFrontendConnectionStat
   }
 
   protected override async performPingRequest(): Promise<void> {
+    if (!this.connectionProvider['socket'].connected) {
+      this.updateStatus(false);
+      return;
+    }
     try {
       await this.pingService.ping();
       this.updateStatus(this.isOnline.online);
@@ -164,6 +171,8 @@ export class ApplicationConnectionStatusContribution extends TheiaApplicationCon
   private readonly notificationManager: NotificationManager;
   @inject(CreateFeatures)
   private readonly createFeatures: CreateFeatures;
+  @inject(WebSocketConnectionProvider)
+  private readonly connectionProvider: WebSocketConnectionProvider;
 
   private readonly offlineStatusDidChangeEmitter = new Emitter<
     OfflineConnectionStatus | undefined
@@ -190,9 +199,10 @@ export class ApplicationConnectionStatusContribution extends TheiaApplicationCon
   }
 
   protected override handleOffline(): void {
-    const params = {
+    const params = <OfflineMessageParams>{
       port: this.daemonPort.port,
       online: this.isOnline.online,
+      backendConnected: this.connectionProvider['socket'].connected, // https://github.com/arduino/arduino-ide/issues/2081
     };
     this._offlineStatus = offlineConnectionStatusType(params);
     const { text, tooltip } = offlineMessage(params);
@@ -248,6 +258,7 @@ export class ApplicationConnectionStatusContribution extends TheiaApplicationCon
 interface OfflineMessageParams {
   readonly port: string | undefined;
   readonly online: boolean;
+  readonly backendConnected: boolean;
 }
 interface OfflineMessage {
   readonly text: string;
@@ -272,8 +283,8 @@ export function offlineMessage(params: OfflineMessageParams): OfflineMessage {
 function offlineConnectionStatusType(
   params: OfflineMessageParams
 ): OfflineConnectionStatus {
-  const { port, online } = params;
-  if (port && online) {
+  const { port, online, backendConnected } = params;
+  if (!backendConnected || (port && online)) {
     return 'backend';
   }
   if (!port) {
diff --git a/arduino-ide-extension/src/test/browser/connection-status-service.test.ts b/arduino-ide-extension/src/test/browser/connection-status-service.test.ts
index 1f1228ce6..c84eade55 100644
--- a/arduino-ide-extension/src/test/browser/connection-status-service.test.ts
+++ b/arduino-ide-extension/src/test/browser/connection-status-service.test.ts
@@ -20,25 +20,41 @@ disableJSDOM();
 describe('connection-status-service', () => {
   describe('offlineMessage', () => {
     it('should warn about the offline backend if connected to both CLI daemon and Internet but offline', () => {
-      const actual = offlineMessage({ port: '50051', online: true });
+      const actual = offlineMessage({
+        port: '50051',
+        online: true,
+        backendConnected: false,
+      });
       expect(actual.text).to.be.equal(backendOfflineText);
       expect(actual.tooltip).to.be.equal(backendOfflineTooltip);
     });
 
     it('should warn about the offline CLI daemon if the CLI daemon port is missing but has Internet connection', () => {
-      const actual = offlineMessage({ port: undefined, online: true });
+      const actual = offlineMessage({
+        port: undefined,
+        online: true,
+        backendConnected: true,
+      });
       expect(actual.text.endsWith(daemonOfflineText)).to.be.true;
       expect(actual.tooltip).to.be.equal(daemonOfflineTooltip);
     });
 
     it('should warn about the offline CLI daemon if the CLI daemon port is missing and has no Internet connection', () => {
-      const actual = offlineMessage({ port: undefined, online: false });
+      const actual = offlineMessage({
+        port: undefined,
+        online: false,
+        backendConnected: true,
+      });
       expect(actual.text.endsWith(daemonOfflineText)).to.be.true;
       expect(actual.tooltip).to.be.equal(daemonOfflineTooltip);
     });
 
     it('should warn about no Internet connection if CLI daemon port is available but the Internet connection is offline', () => {
-      const actual = offlineMessage({ port: '50051', online: false });
+      const actual = offlineMessage({
+        port: '50051',
+        online: false,
+        backendConnected: true,
+      });
       expect(actual.text.endsWith(offlineText)).to.be.true;
       expect(actual.tooltip).to.be.equal(offlineTooltip);
     });