diff --git a/arduino-ide-extension/src/browser/arduino-ide-frontend-module.ts b/arduino-ide-extension/src/browser/arduino-ide-frontend-module.ts
index f481dfc21..89b2b218d 100644
--- a/arduino-ide-extension/src/browser/arduino-ide-frontend-module.ts
+++ b/arduino-ide-extension/src/browser/arduino-ide-frontend-module.ts
@@ -180,7 +180,7 @@ import { TabBarRenderer } from './theia/core/tab-bars';
 import { EditorCommandContribution } from './theia/editor/editor-command';
 import { NavigatorTabBarDecorator as TheiaNavigatorTabBarDecorator } from '@theia/navigator/lib/browser/navigator-tab-bar-decorator';
 import { NavigatorTabBarDecorator } from './theia/navigator/navigator-tab-bar-decorator';
-import { Debug } from './contributions/debug';
+import { Debug, DebugDisabledStatusMessageSource } from './contributions/debug';
 import { Sketchbook } from './contributions/sketchbook';
 import { DebugFrontendApplicationContribution } from './theia/debug/debug-frontend-application-contribution';
 import { DebugFrontendApplicationContribution as TheiaDebugFrontendApplicationContribution } from '@theia/debug/lib/browser/debug-frontend-application-contribution';
@@ -365,7 +365,8 @@ import { AutoSelectProgrammer } from './contributions/auto-select-programmer';
 import { HostedPluginSupport } from './hosted/hosted-plugin-support';
 import { DebugSessionManager as TheiaDebugSessionManager } from '@theia/debug/lib/browser/debug-session-manager';
 import { DebugSessionManager } from './theia/debug/debug-session-manager';
-import { DebugWidget } from '@theia/debug/lib/browser/view/debug-widget';
+import { DebugWidget as TheiaDebugWidget } from '@theia/debug/lib/browser/view/debug-widget';
+import { DebugWidget } from './theia/debug/debug-widget';
 import { DebugViewModel } from '@theia/debug/lib/browser/view/debug-view-model';
 import { DebugSessionWidget } from '@theia/debug/lib/browser/view/debug-session-widget';
 import { DebugConfigurationWidget } from './theia/debug/debug-configuration-widget';
@@ -771,6 +772,8 @@ export default new ContainerModule((bind, unbind, isBound, rebind) => {
   bindContributionProvider(bind, StartupTaskProvider);
   bind(StartupTaskProvider).toService(BoardsServiceProvider); // to reuse the boards config in another window
 
+  bind(DebugDisabledStatusMessageSource).toService(Debug);
+
   // Disabled the quick-pick customization from Theia when multiple formatters are available.
   // Use the default VS Code behavior, and pick the first one. In the IDE2, clang-format has `exclusive` selectors.
   bind(MonacoFormattingConflictsContribution).toSelf().inSingletonScope();
@@ -874,7 +877,7 @@ export default new ContainerModule((bind, unbind, isBound, rebind) => {
   // Customized debug widget with its customized config <select> to update it programmatically.
   bind(WidgetFactory)
     .toDynamicValue(({ container }) => ({
-      id: DebugWidget.ID,
+      id: TheiaDebugWidget.ID,
       createWidget: () => {
         const child = new Container({ defaultScope: 'Singleton' });
         child.parent = container;
diff --git a/arduino-ide-extension/src/browser/contributions/debug.ts b/arduino-ide-extension/src/browser/contributions/debug.ts
index d1f205051..cc49b3809 100644
--- a/arduino-ide-extension/src/browser/contributions/debug.ts
+++ b/arduino-ide-extension/src/browser/contributions/debug.ts
@@ -64,8 +64,26 @@ interface StartDebugParams {
 }
 type StartDebugResult = boolean;
 
+export const DebugDisabledStatusMessageSource = Symbol(
+  'DebugDisabledStatusMessageSource'
+);
+export interface DebugDisabledStatusMessageSource {
+  /**
+   * `undefined` if debugging is enabled (for the currently selected board + programmer + config options).
+   * Otherwise, it's the human readable message why it's disabled.
+   */
+  get message(): string | undefined;
+  /**
+   * Emits an event when {@link message} changes.
+   */
+  get onDidChangeMessage(): Event<string | undefined>;
+}
+
 @injectable()
-export class Debug extends SketchContribution {
+export class Debug
+  extends SketchContribution
+  implements DebugDisabledStatusMessageSource
+{
   @inject(HostedPluginSupport)
   private readonly hostedPluginSupport: HostedPluginSupport;
   @inject(NotificationCenter)
@@ -83,10 +101,10 @@ export class Debug extends SketchContribution {
    * If `undefined`, debugging is enabled. Otherwise, the human-readable reason why it's disabled.
    */
   private _message?: string = noBoardSelected; // Initial pessimism.
-  private didChangeMessageEmitter = new Emitter<string | undefined>();
-  private onDidChangeMessage = this.didChangeMessageEmitter.event;
+  private readonly didChangeMessageEmitter = new Emitter<string | undefined>();
+  readonly onDidChangeMessage = this.didChangeMessageEmitter.event;
 
-  private get message(): string | undefined {
+  get message(): string | undefined {
     return this._message;
   }
   private set message(message: string | undefined) {
@@ -349,6 +367,8 @@ export namespace Debug {
 }
 
 /**
+ * Resolves with the FQBN to use for the `debug --info --programmer p --fqbn $FQBN` command. Otherwise, rejects.
+ *
  * (non-API)
  */
 export async function isDebugEnabled(
diff --git a/arduino-ide-extension/src/browser/style/debug.css b/arduino-ide-extension/src/browser/style/debug.css
index 62f2a07f9..a5a37abd9 100644
--- a/arduino-ide-extension/src/browser/style/debug.css
+++ b/arduino-ide-extension/src/browser/style/debug.css
@@ -1,36 +1,13 @@
-/* TODO: remove after https://github.com/eclipse-theia/theia/pull/9256/ */
-
-/* To fix colors in Theia. */
-.theia-debug-hover-title.number,
-.theia-debug-console-variable.number {
-    color: var(--theia-variable-number-variable-color);
-}
-.theia-debug-hover-title.boolean,
-.theia-debug-console-variable.boolean {
-    color: var(--theia-variable-boolean-variable-color);
-}
-.theia-debug-hover-title.string,
-.theia-debug-console-variable.string {
-    color: var(--theia-variable-string-variable-color);
+/* Naive way of hiding the debug widget when the debug functionality is disabled https://github.com/arduino/arduino-ide/issues/14 */
+.theia-debug-container .debug-toolbar.hidden,
+.theia-debug-container .theia-session-container.hidden {
+    visibility: hidden;
 }
 
-/* To unset the default debug hover dimension. */
-.theia-debug-hover {
-    min-width: unset;
-    min-height: unset;
-    width: unset;
-    height: unset;
-}
-
-/* To adjust the left padding in the hover title. */
-.theia-debug-hover-title {
-    padding-left: 5px;
-}
+.theia-debug-container .status-message {
+    font-family: "Open Sans";
+    font-style: normal;
+    font-size: 12px;
 
-/* Use the default Theia dimensions only iff the expression is complex (`!!expression.hasChildren~) */
-.theia-debug-hover.complex-value {
-    min-width: 324px;
-    min-height: 324px;
-    width: 324px;
-    height: 324px;
+    padding: 10px;
 }
diff --git a/arduino-ide-extension/src/browser/theia/debug/debug-configuration-widget.tsx b/arduino-ide-extension/src/browser/theia/debug/debug-configuration-widget.tsx
index 7d05a4b68..cabaabf39 100644
--- a/arduino-ide-extension/src/browser/theia/debug/debug-configuration-widget.tsx
+++ b/arduino-ide-extension/src/browser/theia/debug/debug-configuration-widget.tsx
@@ -1,3 +1,4 @@
+import { SelectOption } from '@theia/core/lib/browser/widgets/select-component';
 import { DisposableCollection } from '@theia/core/lib/common/disposable';
 import { nls } from '@theia/core/lib/common/nls';
 import { injectable } from '@theia/core/shared/inversify';
@@ -51,6 +52,24 @@ class DebugConfigurationSelect extends TheiaDebugConfigurationSelect {
     );
   }
 
+  protected override renderOptions(): SelectOption[] {
+    const options = super.renderOptions();
+    const addConfiguration = options[options.length - 1];
+    const separator = options[options.length - 2];
+    // Remove "Add configuration..." and the preceding separator options.
+    // They're expected to be the last two items.
+    if (
+      addConfiguration.value ===
+        TheiaDebugConfigurationSelect.ADD_CONFIGURATION &&
+      separator.separator
+    ) {
+      options.splice(options.length - 2, 2);
+      return options;
+    }
+    // Something is unexpected with the select options.
+    return options;
+  }
+
   override componentWillUnmount(): void {
     this.toDisposeOnUnmount.dispose();
   }
diff --git a/arduino-ide-extension/src/browser/theia/debug/debug-widget.ts b/arduino-ide-extension/src/browser/theia/debug/debug-widget.ts
new file mode 100644
index 000000000..cca4d1b06
--- /dev/null
+++ b/arduino-ide-extension/src/browser/theia/debug/debug-widget.ts
@@ -0,0 +1,57 @@
+import {
+  codicon,
+  PanelLayout,
+  Widget,
+} from '@theia/core/lib/browser/widgets/widget';
+import {
+  inject,
+  injectable,
+  postConstruct,
+} from '@theia/core/shared/inversify';
+import { DebugWidget as TheiaDebugWidget } from '@theia/debug/lib/browser/view/debug-widget';
+import { DebugDisabledStatusMessageSource } from '../../contributions/debug';
+
+@injectable()
+export class DebugWidget extends TheiaDebugWidget {
+  @inject(DebugDisabledStatusMessageSource)
+  private readonly debugStatusMessageSource: DebugDisabledStatusMessageSource;
+
+  private readonly statusMessageWidget = new Widget();
+  private readonly messageNode = document.createElement('div');
+
+  @postConstruct()
+  protected override init(): void {
+    super.init();
+    this.messageNode.classList.add('status-message', 'noselect');
+    this.statusMessageWidget.node.appendChild(this.messageNode);
+    this.updateState();
+    this.toDisposeOnDetach.pushAll([
+      this.debugStatusMessageSource.onDidChangeMessage((message) =>
+        this.updateState(message)
+      ),
+      this.statusMessageWidget,
+    ]);
+  }
+
+  private updateState(message = this.debugStatusMessageSource.message): void {
+    requestAnimationFrame(() => {
+      this.messageNode.textContent = message ?? '';
+      const enabled = !message;
+      updateVisibility(enabled, this.toolbar, this.sessionWidget);
+      if (this.layout instanceof PanelLayout) {
+        if (enabled) {
+          this.layout.removeWidget(this.statusMessageWidget);
+        } else {
+          this.layout.insertWidget(0, this.statusMessageWidget);
+        }
+      }
+      this.title.iconClass = enabled ? codicon('debug-alt') : 'fa fa-ban'; // TODO: find a better icon?
+    });
+  }
+}
+
+function updateVisibility(visible: boolean, ...widgets: Widget[]): void {
+  widgets.forEach((widget) =>
+    visible ? widget.removeClass('hidden') : widget.addClass('hidden')
+  );
+}