diff --git a/packages/debug/src/browser/debug-session-manager.ts b/packages/debug/src/browser/debug-session-manager.ts
index 1b0bd4b9f474a..d5decd2125dc5 100644
--- a/packages/debug/src/browser/debug-session-manager.ts
+++ b/packages/debug/src/browser/debug-session-manager.ts
@@ -27,7 +27,7 @@ import { DebugConfiguration } from '../common/debug-common';
 import { DebugError, DebugService } from '../common/debug-service';
 import { BreakpointManager } from './breakpoint/breakpoint-manager';
 import { DebugConfigurationManager } from './debug-configuration-manager';
-import { DebugSession, DebugState } from './debug-session';
+import { DebugSession, DebugState, debugStateContextValue } from './debug-session';
 import { DebugSessionContributionRegistry, DebugSessionFactory } from './debug-session-contribution';
 import { DebugCompoundRoot, DebugCompoundSessionOptions, DebugConfigurationSessionOptions, DebugSessionOptions, InternalDebugSessionOptions } from './debug-session-options';
 import { DebugStackFrame } from './model/debug-stack-frame';
@@ -106,7 +106,9 @@ export class DebugSessionManager {
     protected readonly onDidChangeEmitter = new Emitter<DebugSession | undefined>();
     readonly onDidChange: Event<DebugSession | undefined> = this.onDidChangeEmitter.event;
     protected fireDidChange(current: DebugSession | undefined): void {
+        this.debugTypeKey.set(current?.configuration.type);
         this.inDebugModeKey.set(this.inDebugMode);
+        this.debugStateKey.set(debugStateContextValue(this.state));
         this.onDidChangeEmitter.fire(current);
     }
 
@@ -154,11 +156,13 @@ export class DebugSessionManager {
 
     protected debugTypeKey: ContextKey<string>;
     protected inDebugModeKey: ContextKey<boolean>;
+    protected debugStateKey: ContextKey<string>;
 
     @postConstruct()
     protected init(): void {
         this.debugTypeKey = this.contextKeyService.createKey<string>('debugType', undefined);
         this.inDebugModeKey = this.contextKeyService.createKey<boolean>('inDebugMode', this.inDebugMode);
+        this.debugStateKey = this.contextKeyService.createKey<string>('debugState', debugStateContextValue(this.state));
         this.breakpoints.onDidChangeMarkers(uri => this.fireDidChangeBreakpoints({ uri }));
         this.labelProvider.onDidChange(event => {
             for (const uriString of this.breakpoints.getUris()) {
diff --git a/packages/debug/src/browser/debug-session.tsx b/packages/debug/src/browser/debug-session.tsx
index 130885be8d19b..c8825227121e2 100644
--- a/packages/debug/src/browser/debug-session.tsx
+++ b/packages/debug/src/browser/debug-session.tsx
@@ -50,6 +50,18 @@ export enum DebugState {
     Running,
     Stopped
 }
+/**
+ * The mapped string values must not change as they are used for the `debugState` when context closure.
+ * For more details see the `Debugger contexts` section of the [official doc](https://code.visualstudio.com/api/references/when-clause-contexts#available-contexts).
+ */
+export function debugStateContextValue(state: DebugState): string {
+    switch (state) {
+        case DebugState.Initializing: return 'initializing';
+        case DebugState.Stopped: return 'stopped';
+        case DebugState.Running: return 'running';
+        default: return 'inactive';
+    }
+}
 
 // FIXME: make injectable to allow easily inject services
 export class DebugSession implements CompositeTreeElement {
@@ -74,7 +86,7 @@ export class DebugSession implements CompositeTreeElement {
     protected readonly childSessions = new Map<string, DebugSession>();
     protected readonly toDispose = new DisposableCollection();
 
-    private isStopping: boolean = false;
+    protected isStopping: boolean = false;
 
     constructor(
         readonly id: string,
@@ -89,6 +101,10 @@ export class DebugSession implements CompositeTreeElement {
         protected readonly fileService: FileService,
         protected readonly debugContributionProvider: ContributionProvider<DebugContribution>,
         protected readonly workspaceService: WorkspaceService,
+        /**
+         * Number of millis after a `stop` request times out. It's 5 seconds by default.
+         */
+        protected readonly stopTimeout = 5_000,
     ) {
         this.connection.onRequest('runInTerminal', (request: DebugProtocol.RunInTerminalRequest) => this.runInTerminal(request));
         this.connection.onDidClose(() => {
@@ -274,19 +290,25 @@ export class DebugSession implements CompositeTreeElement {
     }
 
     protected async initialize(): Promise<void> {
-        const response = await this.connection.sendRequest('initialize', {
-            clientID: 'Theia',
-            clientName: 'Theia IDE',
-            adapterID: this.configuration.type,
-            locale: 'en-US',
-            linesStartAt1: true,
-            columnsStartAt1: true,
-            pathFormat: 'path',
-            supportsVariableType: false,
-            supportsVariablePaging: false,
-            supportsRunInTerminalRequest: true
-        });
-        this.updateCapabilities(response?.body || {});
+        try {
+            const response = await this.connection.sendRequest('initialize', {
+                clientID: 'Theia',
+                clientName: 'Theia IDE',
+                adapterID: this.configuration.type,
+                locale: 'en-US',
+                linesStartAt1: true,
+                columnsStartAt1: true,
+                pathFormat: 'path',
+                supportsVariableType: false,
+                supportsVariablePaging: false,
+                supportsRunInTerminalRequest: true
+            });
+            this.updateCapabilities(response?.body || {});
+            this.didReceiveCapabilities.resolve();
+        } catch (err) {
+            this.didReceiveCapabilities.reject(err);
+            throw err;
+        }
     }
 
     protected async launchOrAttach(): Promise<void> {
@@ -304,8 +326,17 @@ export class DebugSession implements CompositeTreeElement {
         }
     }
 
+    /**
+     * The `send('initialize')` request could resolve later than `on('initialized')` emits the event.
+     * Hence, the `configure` would use the empty object `capabilities`.
+     * Using the empty `capabilities` could result in missing exception breakpoint filters, as
+     * always `capabilities.exceptionBreakpointFilters` is falsy. This deferred promise works
+     * around this timing issue. https://github.com/eclipse-theia/theia/issues/11886
+     */
+    protected didReceiveCapabilities = new Deferred<void>();
     protected initialized = false;
     protected async configure(): Promise<void> {
+        await this.didReceiveCapabilities.promise;
         if (this.capabilities.exceptionBreakpointFilters) {
             const exceptionBreakpoints = [];
             for (const filter of this.capabilities.exceptionBreakpointFilters) {
@@ -340,24 +371,39 @@ export class DebugSession implements CompositeTreeElement {
         if (!this.isStopping) {
             this.isStopping = true;
             if (this.canTerminate()) {
-                const terminated = this.waitFor('terminated', 5000);
+                const terminated = this.waitFor('terminated', this.stopTimeout);
                 try {
-                    await this.connection.sendRequest('terminate', { restart: isRestart }, 5000);
+                    await this.connection.sendRequest('terminate', { restart: isRestart }, this.stopTimeout);
                     await terminated;
                 } catch (e) {
-                    console.error('Did not receive terminated event in time', e);
+                    this.handleTerminateError(e);
                 }
             } else {
+                const terminateDebuggee = this.initialized && this.capabilities.supportTerminateDebuggee;
                 try {
-                    await this.sendRequest('disconnect', { restart: isRestart }, 5000);
+                    await this.sendRequest('disconnect', { restart: isRestart, terminateDebuggee }, this.stopTimeout);
                 } catch (e) {
-                    console.error('Error on disconnect', e);
+                    this.handleDisconnectError(e);
                 }
             }
             callback();
         }
     }
 
+    /**
+     * Invoked when sending the `terminate` request to the debugger is rejected or timed out.
+     */
+    protected handleTerminateError(err: unknown): void {
+        console.error('Did not receive terminated event in time', err);
+    }
+
+    /**
+     * Invoked when sending the `disconnect` request to the debugger is rejected or timed out.
+     */
+    protected handleDisconnectError(err: unknown): void {
+        console.error('Error on disconnect', err);
+    }
+
     async disconnect(isRestart: boolean, callback: () => void): Promise<void> {
         if (!this.isStopping) {
             this.isStopping = true;
@@ -665,12 +711,17 @@ export class DebugSession implements CompositeTreeElement {
                 const response = await this.sendRequest('setFunctionBreakpoints', {
                     breakpoints: enabled.map(b => b.origin.raw)
                 });
-                response.body.breakpoints.forEach((raw, index) => {
-                    // node debug adapter returns more breakpoints sometimes
-                    if (enabled[index]) {
-                        enabled[index].update({ raw });
-                    }
-                });
+                // Apparently, `body` and `breakpoints` can be missing.
+                // https://github.com/eclipse-theia/theia/issues/11885
+                // https://github.com/microsoft/vscode/blob/80004351ccf0884b58359f7c8c801c91bb827d83/src/vs/workbench/contrib/debug/browser/debugSession.ts#L448-L449
+                if (response && response.body) {
+                    response.body.breakpoints.forEach((raw, index) => {
+                        // node debug adapter returns more breakpoints sometimes
+                        if (enabled[index]) {
+                            enabled[index].update({ raw });
+                        }
+                    });
+                }
             } catch (error) {
                 // could be error or promise rejection of DebugProtocol.SetFunctionBreakpoints
                 if (error instanceof Error) {
@@ -699,10 +750,12 @@ export class DebugSession implements CompositeTreeElement {
         );
         const enabled = all.filter(b => b.enabled);
         try {
+            const breakpoints = enabled.map(({ origin }) => origin.raw);
             const response = await this.sendRequest('setBreakpoints', {
                 source: source.raw,
                 sourceModified,
-                breakpoints: enabled.map(({ origin }) => origin.raw)
+                breakpoints,
+                lines: breakpoints.map(({ line }) => line)
             });
             response.body.breakpoints.forEach((raw, index) => {
                 // node debug adapter returns more breakpoints sometimes
diff --git a/packages/debug/src/browser/model/debug-stack-frame.tsx b/packages/debug/src/browser/model/debug-stack-frame.tsx
index 9e70411c4337b..67b3c14ced513 100644
--- a/packages/debug/src/browser/model/debug-stack-frame.tsx
+++ b/packages/debug/src/browser/model/debug-stack-frame.tsx
@@ -64,28 +64,36 @@ export class DebugStackFrame extends DebugStackFrameData implements TreeElement
         }));
     }
 
-    async open(options: WidgetOpenerOptions = {
-        mode: 'reveal'
-    }): Promise<EditorWidget | undefined> {
+    async open(options?: WidgetOpenerOptions): Promise<EditorWidget | undefined> {
         if (!this.source) {
             return undefined;
         }
         const { line, column, endLine, endColumn } = this.raw;
         const selection: RecursivePartial<Range> = {
-            start: Position.create(line - 1, column - 1)
+            start: Position.create(this.clampPositive(line - 1), this.clampPositive(column - 1))
         };
         if (typeof endLine === 'number') {
             selection.end = {
-                line: endLine - 1,
-                character: typeof endColumn === 'number' ? endColumn - 1 : undefined
+                line: this.clampPositive(endLine - 1),
+                character: typeof endColumn === 'number' ? this.clampPositive(endColumn - 1) : undefined
             };
         }
         this.source.open({
+            mode: 'reveal',
             ...options,
             selection
         });
     }
 
+    /**
+     * Debugger can send `column: 0` value despite of initializing the debug session with `columnsStartAt1: true`.
+     * This method can be used to ensure that neither `column` nor `column` are negative numbers.
+     * See https://github.com/microsoft/vscode-mock-debug/issues/85.
+     */
+    protected clampPositive(value: number): number {
+        return Math.max(value, 0);
+    }
+
     protected scopes: Promise<DebugScope[]> | undefined;
     getScopes(): Promise<DebugScope[]> {
         return this.scopes || (this.scopes = this.doGetScopes());
diff --git a/packages/debug/src/browser/style/index.css b/packages/debug/src/browser/style/index.css
index 68a694ee7ed0e..df1f8be4c3fef 100644
--- a/packages/debug/src/browser/style/index.css
+++ b/packages/debug/src/browser/style/index.css
@@ -146,6 +146,17 @@
     opacity: 1;
 }
 
+.debug-toolbar .debug-action>div {
+    font-family: var(--theia-ui-font-family);
+    font-size: var(--theia-ui-font-size0);
+    display: flex;
+    align-items: center;
+    align-self: center;
+    justify-content: center;
+    text-align: center;
+    min-height: inherit;
+}
+
 /** Console */
 
 #debug-console .theia-console-info {
diff --git a/packages/debug/src/browser/view/debug-action.tsx b/packages/debug/src/browser/view/debug-action.tsx
index 4be5ec9d93956..f7ef0a3c19b5b 100644
--- a/packages/debug/src/browser/view/debug-action.tsx
+++ b/packages/debug/src/browser/view/debug-action.tsx
@@ -21,7 +21,10 @@ export class DebugAction extends React.Component<DebugAction.Props> {
 
     override render(): React.ReactNode {
         const { enabled, label, iconClass } = this.props;
-        const classNames = ['debug-action', ...codiconArray(iconClass, true)];
+        const classNames = ['debug-action'];
+        if (iconClass) {
+            classNames.push(...codiconArray(iconClass, true));
+        }
         if (enabled === false) {
             classNames.push(DISABLED_CLASS);
         }
@@ -29,7 +32,9 @@ export class DebugAction extends React.Component<DebugAction.Props> {
             className={classNames.join(' ')}
             title={label}
             onClick={this.props.run}
-            ref={this.setRef} />;
+            ref={this.setRef} >
+            {!iconClass && <div>{label}</div>}
+        </span>;
     }
 
     focus(): void {
diff --git a/packages/debug/src/browser/view/debug-toolbar-widget.tsx b/packages/debug/src/browser/view/debug-toolbar-widget.tsx
index 705c29f6c19bc..66c3d0c08d8db 100644
--- a/packages/debug/src/browser/view/debug-toolbar-widget.tsx
+++ b/packages/debug/src/browser/view/debug-toolbar-widget.tsx
@@ -16,7 +16,8 @@
 
 import * as React from '@theia/core/shared/react';
 import { inject, postConstruct, injectable } from '@theia/core/shared/inversify';
-import { Disposable, DisposableCollection, MenuPath } from '@theia/core';
+import { CommandMenuNode, CommandRegistry, CompoundMenuNode, Disposable, DisposableCollection, MenuModelRegistry, MenuPath } from '@theia/core';
+import { ContextKeyService } from '@theia/core/lib/browser/context-key-service';
 import { ReactWidget } from '@theia/core/lib/browser/widgets';
 import { DebugViewModel } from './debug-view-model';
 import { DebugState } from '../debug-session';
@@ -28,8 +29,10 @@ export class DebugToolBar extends ReactWidget {
 
     static readonly MENU: MenuPath = ['debug-toolbar-menu'];
 
-    @inject(DebugViewModel)
-    protected readonly model: DebugViewModel;
+    @inject(CommandRegistry) protected readonly commandRegistry: CommandRegistry;
+    @inject(MenuModelRegistry) protected readonly menuModelRegistry: MenuModelRegistry;
+    @inject(ContextKeyService) protected readonly contextKeyService: ContextKeyService;
+    @inject(DebugViewModel) protected readonly model: DebugViewModel;
 
     protected readonly onRender = new DisposableCollection();
 
@@ -65,6 +68,7 @@ export class DebugToolBar extends ReactWidget {
     protected render(): React.ReactNode {
         const { state } = this.model;
         return <React.Fragment>
+            {this.renderContributedCommands()}
             {this.renderContinue()}
             <DebugAction enabled={state === DebugState.Stopped} run={this.stepOver} label={nls.localizeByDefault('Step Over')}
                 iconClass='debug-step-over' ref={this.setStepRef} />
@@ -77,6 +81,43 @@ export class DebugToolBar extends ReactWidget {
             {this.renderStart()}
         </React.Fragment>;
     }
+
+    protected renderContributedCommands(): React.ReactNode {
+        const debugActions: React.ReactNode[] = [];
+        // first, search for CompoundMenuNodes:
+        this.menuModelRegistry.getMenu(DebugToolBar.MENU).children.forEach(compoundMenuNode => {
+            if (CompoundMenuNode.is(compoundMenuNode) && this.matchContext(compoundMenuNode.when)) {
+                // second, search for nested CommandMenuNodes:
+                compoundMenuNode.children.forEach(commandMenuNode => {
+                    if (CommandMenuNode.is(commandMenuNode) && this.matchContext(commandMenuNode.when)) {
+                        debugActions.push(this.debugAction(commandMenuNode));
+                    }
+                });
+            }
+        });
+        return debugActions;
+    }
+
+    protected matchContext(when?: string): boolean {
+        return !when || this.contextKeyService.match(when);
+    }
+
+    protected debugAction(commandMenuNode: CommandMenuNode): React.ReactNode {
+        const { command, icon = '', label = '' } = commandMenuNode;
+        if (!label && !icon) {
+            const { when } = commandMenuNode;
+            console.warn(`Neither 'label' nor 'icon' properties were defined for the command menu node. (${JSON.stringify({ command, when })}}. Skipping.`);
+            return;
+        }
+        const run = () => this.commandRegistry.executeCommand(command);
+        return <DebugAction
+            key={command}
+            enabled={true}
+            label={label}
+            iconClass={icon}
+            run={run} />;
+    }
+
     protected renderStart(): React.ReactNode {
         const { state } = this.model;
         if (state === DebugState.Inactive && this.model.sessionCount === 1) {
diff --git a/packages/editor/src/browser/editor-manager.ts b/packages/editor/src/browser/editor-manager.ts
index b9243d3256a6b..a30e6ea4f5ca3 100644
--- a/packages/editor/src/browser/editor-manager.ts
+++ b/packages/editor/src/browser/editor-manager.ts
@@ -253,6 +253,12 @@ export class EditorManager extends NavigatableWidgetOpenHandler<EditorWidget> {
 
     protected getSelection(widget: EditorWidget, selection: RecursivePartial<Range>): Range | Position | undefined {
         const { start, end } = selection;
+        if (Position.is(start)) {
+            if (Position.is(end)) {
+                return widget.editor.document.toValidRange({ start, end });
+            }
+            return widget.editor.document.toValidPosition(start);
+        }
         const line = start && start.line !== undefined && start.line >= 0 ? start.line : undefined;
         if (line === undefined) {
             return undefined;
diff --git a/packages/editor/src/browser/editor.ts b/packages/editor/src/browser/editor.ts
index 2326e52b583b3..97367f57f6935 100644
--- a/packages/editor/src/browser/editor.ts
+++ b/packages/editor/src/browser/editor.ts
@@ -33,6 +33,17 @@ export interface TextEditorDocument extends lsp.TextDocument, Saveable, Disposab
      * @since 1.8.0
      */
     findMatches?(options: FindMatchesOptions): FindMatch[];
+    /**
+     * Creates a valid position. If the position is outside of the backing document, this method will return a position that is ensured to be inside the document and valid.
+     * For example, when the `position` is `{ line: 1, character: 0 }` and the document is empty, this method will return with `{ line: 0, character: 0 }`.
+     */
+    toValidPosition(position: Position): Position;
+    /**
+     * Creates a valid range. If the `range` argument is outside of the document, this method will return with a new range that does not exceed the boundaries of the document.
+     * For example, if the argument is `{ start: { line: 1, character: 0 }, end: { line: 1, character: 0 } }` and the document is empty, the return value is
+     * `{ start: { line: 0, character: 0 }, end: { line: 0, character: 0 } }`.
+     */
+    toValidRange(range: Range): Range;
 }
 
 // Refactoring
diff --git a/packages/monaco/src/browser/monaco-editor-model.ts b/packages/monaco/src/browser/monaco-editor-model.ts
index 105c1fc2d473f..cd0f4b36e0e48 100644
--- a/packages/monaco/src/browser/monaco-editor-model.ts
+++ b/packages/monaco/src/browser/monaco-editor-model.ts
@@ -293,6 +293,15 @@ export class MonacoEditorModel implements IResolvedTextEditorModel, TextEditorDo
         return this.model.getLineMaxColumn(lineNumber);
     }
 
+    toValidPosition(position: Position): Position {
+        const { lineNumber, column } = this.model.validatePosition(this.p2m.asPosition(position));
+        return this.m2p.asPosition(lineNumber, column);
+    }
+
+    toValidRange(range: Range): Range {
+        return this.m2p.asRange(this.model.validateRange(this.p2m.asRange(range)));
+    }
+
     get readOnly(): boolean {
         return this.resource.saveContents === undefined;
     }
diff --git a/packages/plugin-ext/src/common/plugin-api-rpc.ts b/packages/plugin-ext/src/common/plugin-api-rpc.ts
index d803933c75dc5..e31f1085bffa4 100644
--- a/packages/plugin-ext/src/common/plugin-api-rpc.ts
+++ b/packages/plugin-ext/src/common/plugin-api-rpc.ts
@@ -1800,6 +1800,7 @@ export interface DebugExt {
     $onSessionCustomEvent(sessionId: string, event: string, body?: any): void;
     $breakpointsDidChange(added: Breakpoint[], removed: string[], changed: Breakpoint[]): void;
     $sessionDidCreate(sessionId: string): void;
+    $sessionDidStart(sessionId: string): void;
     $sessionDidDestroy(sessionId: string): void;
     $sessionDidChange(sessionId: string | undefined): void;
     $provideDebugConfigurationsByHandle(handle: number, workspaceFolder: string | undefined): Promise<theia.DebugConfiguration[]>;
diff --git a/packages/plugin-ext/src/main/browser/debug/debug-main.ts b/packages/plugin-ext/src/main/browser/debug/debug-main.ts
index cbeb416440475..4221473312236 100644
--- a/packages/plugin-ext/src/main/browser/debug/debug-main.ts
+++ b/packages/plugin-ext/src/main/browser/debug/debug-main.ts
@@ -114,6 +114,7 @@ export class DebugMainImpl implements DebugMain, Disposable {
             this.breakpointsManager.onDidChangeBreakpoints(fireDidChangeBreakpoints),
             this.breakpointsManager.onDidChangeFunctionBreakpoints(fireDidChangeBreakpoints),
             this.sessionManager.onDidCreateDebugSession(debugSession => this.debugExt.$sessionDidCreate(debugSession.id)),
+            this.sessionManager.onDidStartDebugSession(debugSession => this.debugExt.$sessionDidStart(debugSession.id)),
             this.sessionManager.onDidDestroyDebugSession(debugSession => this.debugExt.$sessionDidDestroy(debugSession.id)),
             this.sessionManager.onDidChangeActiveDebugSession(event => this.debugExt.$sessionDidChange(event.current && event.current.id)),
             this.sessionManager.onDidReceiveDebugSessionCustomEvent(event => this.debugExt.$onSessionCustomEvent(event.session.id, event.event, event.body))
diff --git a/packages/plugin-ext/src/main/browser/menus/plugin-menu-command-adapter.ts b/packages/plugin-ext/src/main/browser/menus/plugin-menu-command-adapter.ts
index a76881060108c..bd82d054dbb38 100644
--- a/packages/plugin-ext/src/main/browser/menus/plugin-menu-command-adapter.ts
+++ b/packages/plugin-ext/src/main/browser/menus/plugin-menu-command-adapter.ts
@@ -89,6 +89,7 @@ export class PluginMenuCommandAdapter implements MenuCommandAdapter {
             ['comments/comment/title', toCommentArgs],
             ['comments/commentThread/context', toCommentArgs],
             ['debug/callstack/context', firstArgOnly],
+            ['debug/variables/context', firstArgOnly],
             ['debug/toolBar', noArgs],
             ['editor/context', selectedResource],
             ['editor/title', widgetURI],
diff --git a/packages/plugin-ext/src/main/browser/menus/vscode-theia-menu-mappings.ts b/packages/plugin-ext/src/main/browser/menus/vscode-theia-menu-mappings.ts
index 4b7c47f157871..97c04d2bb387c 100644
--- a/packages/plugin-ext/src/main/browser/menus/vscode-theia-menu-mappings.ts
+++ b/packages/plugin-ext/src/main/browser/menus/vscode-theia-menu-mappings.ts
@@ -21,6 +21,8 @@ import { injectable } from '@theia/core/shared/inversify';
 import { URI as CodeUri } from '@theia/core/shared/vscode-uri';
 import { DebugStackFramesWidget } from '@theia/debug/lib/browser/view/debug-stack-frames-widget';
 import { DebugThreadsWidget } from '@theia/debug/lib/browser/view/debug-threads-widget';
+import { DebugToolBar } from '@theia/debug/lib/browser/view/debug-toolbar-widget';
+import { DebugVariablesWidget } from '@theia/debug/lib/browser/view/debug-variables-widget';
 import { EditorWidget, EDITOR_CONTEXT_MENU } from '@theia/editor/lib/browser';
 import { NAVIGATOR_CONTEXT_MENU } from '@theia/navigator/lib/browser/navigator-contribution';
 import { ScmTreeWidget } from '@theia/scm/lib/browser/scm-tree-widget';
@@ -38,6 +40,8 @@ export const implementedVSCodeContributionPoints = [
     'comments/comment/title',
     'comments/commentThread/context',
     'debug/callstack/context',
+    'debug/variables/context',
+    'debug/toolBar',
     'editor/context',
     'editor/title',
     'editor/title/context',
@@ -59,6 +63,8 @@ export const codeToTheiaMappings = new Map<ContributionPoint, MenuPath[]>([
     ['comments/comment/title', [COMMENT_TITLE]],
     ['comments/commentThread/context', [COMMENT_THREAD_CONTEXT]],
     ['debug/callstack/context', [DebugStackFramesWidget.CONTEXT_MENU, DebugThreadsWidget.CONTEXT_MENU]],
+    ['debug/variables/context', [DebugVariablesWidget.CONTEXT_MENU]],
+    ['debug/toolBar', [DebugToolBar.MENU]],
     ['editor/context', [EDITOR_CONTEXT_MENU]],
     ['editor/title', [PLUGIN_EDITOR_TITLE_MENU]],
     ['editor/title/context', [SHELL_TABBAR_CONTEXT_MENU]],
diff --git a/packages/plugin-ext/src/plugin/debug/debug-ext.ts b/packages/plugin-ext/src/plugin/debug/debug-ext.ts
index 146d4d3b65d71..4bf42e7129a50 100644
--- a/packages/plugin-ext/src/plugin/debug/debug-ext.ts
+++ b/packages/plugin-ext/src/plugin/debug/debug-ext.ts
@@ -67,6 +67,7 @@ export class DebugExtImpl implements DebugExt {
     private readonly onDidChangeBreakpointsEmitter = new Emitter<theia.BreakpointsChangeEvent>();
     private readonly onDidChangeActiveDebugSessionEmitter = new Emitter<theia.DebugSession | undefined>();
     private readonly onDidTerminateDebugSessionEmitter = new Emitter<theia.DebugSession>();
+    private readonly onDidCreateDebugSessionEmitter = new Emitter<theia.DebugSession>();
     private readonly onDidStartDebugSessionEmitter = new Emitter<theia.DebugSession>();
     private readonly onDidReceiveDebugSessionCustomEmitter = new Emitter<theia.DebugSessionCustomEvent>();
 
@@ -131,6 +132,10 @@ export class DebugExtImpl implements DebugExt {
         return this.onDidTerminateDebugSessionEmitter.event;
     }
 
+    get onDidCreateDebugSession(): theia.Event<theia.DebugSession> {
+        return this.onDidCreateDebugSessionEmitter.event;
+    }
+
     get onDidStartDebugSession(): theia.Event<theia.DebugSession> {
         return this.onDidStartDebugSessionEmitter.event;
     }
@@ -253,6 +258,13 @@ export class DebugExtImpl implements DebugExt {
     }
 
     async $sessionDidCreate(sessionId: string): Promise<void> {
+        const session = this.sessions.get(sessionId);
+        if (session) {
+            this.onDidCreateDebugSessionEmitter.fire(session);
+        }
+    }
+
+    async $sessionDidStart(sessionId: string): Promise<void> {
         const session = this.sessions.get(sessionId);
         if (session) {
             this.onDidStartDebugSessionEmitter.fire(session);