diff --git a/src/vs/workbench/contrib/debug/browser/debugSession.ts b/src/vs/workbench/contrib/debug/browser/debugSession.ts
index 00ed0d36faf4c..5b9c4ac37dd35 100644
--- a/src/vs/workbench/contrib/debug/browser/debugSession.ts
+++ b/src/vs/workbench/contrib/debug/browser/debugSession.ts
@@ -832,6 +832,17 @@ export class DebugSession implements IDebugSession {
 				column: event.body.column ? event.body.column : 1,
 				source: this.getSource(event.body.source)
 			} : undefined;
+
+			if (event.body.group === 'start' || event.body.group === 'startCollapsed') {
+				const expanded = event.body.group === 'start';
+				this.repl.startGroup(event.body.output || '', expanded, source);
+				return;
+			}
+			if (event.body.group === 'end') {
+				this.repl.endGroup();
+				// Do not return, the end event can have additional output in it
+			}
+
 			if (event.body.variablesReference) {
 				const container = new ExpressionContainer(this, undefined, event.body.variablesReference, generateUuid());
 				outpuPromises.push(container.getChildren().then(async children => {
diff --git a/src/vs/workbench/contrib/debug/browser/repl.ts b/src/vs/workbench/contrib/debug/browser/repl.ts
index 8677590347cad..338d74cc9514c 100644
--- a/src/vs/workbench/contrib/debug/browser/repl.ts
+++ b/src/vs/workbench/contrib/debug/browser/repl.ts
@@ -51,12 +51,13 @@ import { RunOnceScheduler } from 'vs/base/common/async';
 import { FuzzyScore } from 'vs/base/common/filters';
 import { IClipboardService } from 'vs/platform/clipboard/common/clipboardService';
 import { PANEL_BACKGROUND } from 'vs/workbench/common/theme';
-import { ReplDelegate, ReplVariablesRenderer, ReplSimpleElementsRenderer, ReplEvaluationInputsRenderer, ReplEvaluationResultsRenderer, ReplRawObjectsRenderer, ReplDataSource, ReplAccessibilityProvider } from 'vs/workbench/contrib/debug/browser/replViewer';
+import { ReplDelegate, ReplVariablesRenderer, ReplSimpleElementsRenderer, ReplEvaluationInputsRenderer, ReplEvaluationResultsRenderer, ReplRawObjectsRenderer, ReplDataSource, ReplAccessibilityProvider, ReplGroupRenderer } from 'vs/workbench/contrib/debug/browser/replViewer';
 import { localize } from 'vs/nls';
 import { ViewPane, IViewPaneOptions } from 'vs/workbench/browser/parts/views/viewPaneContainer';
 import { IKeybindingService } from 'vs/platform/keybinding/common/keybinding';
 import { IViewsService, IViewDescriptorService } from 'vs/workbench/common/views';
 import { IOpenerService } from 'vs/platform/opener/common/opener';
+import { ReplGroup } from 'vs/workbench/contrib/debug/common/replModel';
 
 const $ = dom.$;
 
@@ -425,6 +426,16 @@ export class Repl extends ViewPane implements IHistoryNavigationWidget {
 
 			const lastElementVisible = this.tree.scrollTop + this.tree.renderHeight >= this.tree.scrollHeight;
 			await this.tree.updateChildren();
+
+			const session = this.tree.getInput();
+			if (session) {
+				const replElements = session.getReplElements();
+				const lastElement = replElements.length ? replElements[replElements.length - 1] : undefined;
+				if (lastElement instanceof ReplGroup && lastElement.autoExpand) {
+					await this.tree.expand(lastElement);
+				}
+			}
+
 			if (lastElementVisible) {
 				// Only scroll if we were scrolled all the way down before tree refreshed #10486
 				revealLastElement(this.tree);
@@ -454,6 +465,7 @@ export class Repl extends ViewPane implements IHistoryNavigationWidget {
 				this.instantiationService.createInstance(ReplVariablesRenderer, linkDetector),
 				this.instantiationService.createInstance(ReplSimpleElementsRenderer, linkDetector),
 				new ReplEvaluationInputsRenderer(),
+				new ReplGroupRenderer(),
 				new ReplEvaluationResultsRenderer(linkDetector),
 				new ReplRawObjectsRenderer(linkDetector),
 			],
diff --git a/src/vs/workbench/contrib/debug/browser/replViewer.ts b/src/vs/workbench/contrib/debug/browser/replViewer.ts
index de9cd9ce40bf4..53772e842addc 100644
--- a/src/vs/workbench/contrib/debug/browser/replViewer.ts
+++ b/src/vs/workbench/contrib/debug/browser/replViewer.ts
@@ -7,7 +7,7 @@ import severity from 'vs/base/common/severity';
 import * as dom from 'vs/base/browser/dom';
 import { IAccessibilityProvider } from 'vs/base/browser/ui/list/listWidget';
 import { Variable } from 'vs/workbench/contrib/debug/common/debugModel';
-import { SimpleReplElement, RawObjectReplElement, ReplEvaluationInput, ReplEvaluationResult } from 'vs/workbench/contrib/debug/common/replModel';
+import { SimpleReplElement, RawObjectReplElement, ReplEvaluationInput, ReplEvaluationResult, ReplGroup } from 'vs/workbench/contrib/debug/common/replModel';
 import { CachedListVirtualDelegate } from 'vs/base/browser/ui/list/list';
 import { ITreeRenderer, ITreeNode, IAsyncDataSource } from 'vs/base/browser/ui/tree/tree';
 import { IEditorService } from 'vs/workbench/services/editor/common/editorService';
@@ -30,6 +30,10 @@ interface IReplEvaluationInputTemplateData {
 	label: HighlightedLabel;
 }
 
+interface IReplGroupTemplateData {
+	label: HighlightedLabel;
+}
+
 interface IReplEvaluationResultTemplateData {
 	value: HTMLElement;
 	annotation: HTMLElement;
@@ -76,6 +80,29 @@ export class ReplEvaluationInputsRenderer implements ITreeRenderer<ReplEvaluatio
 	}
 }
 
+export class ReplGroupRenderer implements ITreeRenderer<ReplGroup, FuzzyScore, IReplGroupTemplateData> {
+	static readonly ID = 'replGroup';
+
+	get templateId(): string {
+		return ReplGroupRenderer.ID;
+	}
+
+	renderTemplate(container: HTMLElement): IReplEvaluationInputTemplateData {
+		const input = dom.append(container, $('.expression'));
+		const label = new HighlightedLabel(input, false);
+		return { label };
+	}
+
+	renderElement(element: ITreeNode<ReplGroup, FuzzyScore>, _index: number, templateData: IReplGroupTemplateData): void {
+		const replGroup = element.element;
+		templateData.label.set(replGroup.name, createMatches(element.filterData));
+	}
+
+	disposeTemplate(_templateData: IReplEvaluationInputTemplateData): void {
+		// noop
+	}
+}
+
 export class ReplEvaluationResultsRenderer implements ITreeRenderer<ReplEvaluationResult, FuzzyScore, IReplEvaluationResultTemplateData> {
 	static readonly ID = 'replEvaluationResult';
 
@@ -296,6 +323,9 @@ export class ReplDelegate extends CachedListVirtualDelegate<IReplElement> {
 			// Variable with no name is a top level variable which should be rendered like a repl element #17404
 			return ReplSimpleElementsRenderer.ID;
 		}
+		if (element instanceof ReplGroup) {
+			return ReplGroupRenderer.ID;
+		}
 
 		return ReplRawObjectsRenderer.ID;
 	}
@@ -317,7 +347,7 @@ export class ReplDataSource implements IAsyncDataSource<IDebugSession, IReplElem
 			return true;
 		}
 
-		return !!(<IExpressionContainer>element).hasChildren;
+		return !!(<IExpressionContainer | ReplGroup>element).hasChildren;
 	}
 
 	getChildren(element: IReplElement | IDebugSession): Promise<IReplElement[]> {
@@ -327,6 +357,9 @@ export class ReplDataSource implements IAsyncDataSource<IDebugSession, IReplElem
 		if (element instanceof RawObjectReplElement) {
 			return element.getChildren();
 		}
+		if (element instanceof ReplGroup) {
+			return Promise.resolve(element.getChildren());
+		}
 
 		return (<IExpression>element).getChildren();
 	}
@@ -343,6 +376,9 @@ export class ReplAccessibilityProvider implements IAccessibilityProvider<IReplEl
 		if (element instanceof RawObjectReplElement) {
 			return localize('replRawObjectAriaLabel', "Repl variable {0} has value {1}, read eval print loop, debug", element.name, element.value);
 		}
+		if (element instanceof ReplGroup) {
+			return localize('replGroup', "Repl group {0}, read eval print loop, debug", element.name);
+		}
 
 		return '';
 	}
diff --git a/src/vs/workbench/contrib/debug/common/replModel.ts b/src/vs/workbench/contrib/debug/common/replModel.ts
index f9c8ae7c43b28..87d3348b97c8c 100644
--- a/src/vs/workbench/contrib/debug/common/replModel.ts
+++ b/src/vs/workbench/contrib/debug/common/replModel.ts
@@ -120,6 +120,60 @@ export class ReplEvaluationResult extends ExpressionContainer implements IReplEl
 	}
 }
 
+export class ReplGroup implements IReplElement {
+
+	private children: IReplElement[] = [];
+	private id: string;
+	private ended = false;
+	static COUNTER = 0;
+
+	constructor(
+		public name: string,
+		public autoExpand: boolean,
+		public sourceData?: IReplElementSource
+	) {
+		this.id = `replGroup:${ReplGroup.COUNTER++}`;
+	}
+
+	get hasChildren() {
+		return true;
+	}
+
+	getId(): string {
+		return this.id;
+	}
+
+	toString(): string {
+		return this.name;
+	}
+
+	addChild(child: IReplElement): void {
+		const lastElement = this.children.length ? this.children[this.children.length - 1] : undefined;
+		if (lastElement instanceof ReplGroup && !lastElement.hasEnded) {
+			lastElement.addChild(child);
+		} else {
+			this.children.push(child);
+		}
+	}
+
+	getChildren(): IReplElement[] {
+		return this.children;
+	}
+
+	end(): void {
+		const lastElement = this.children.length ? this.children[this.children.length - 1] : undefined;
+		if (lastElement instanceof ReplGroup && !lastElement.hasEnded) {
+			lastElement.end();
+		} else {
+			this.ended = true;
+		}
+	}
+
+	get hasEnded(): boolean {
+		return this.ended;
+	}
+}
+
 export class ReplModel {
 	private replElements: IReplElement[] = [];
 	private readonly _onDidChangeElements = new Emitter<void>();
@@ -162,11 +216,29 @@ export class ReplModel {
 		}
 	}
 
+	startGroup(name: string, autoExpand: boolean, sourceData?: IReplElementSource): void {
+		const group = new ReplGroup(name, autoExpand, sourceData);
+		this.addReplElement(group);
+	}
+
+	endGroup(): void {
+		const lastElement = this.replElements[this.replElements.length - 1];
+		if (lastElement instanceof ReplGroup) {
+			lastElement.end();
+		}
+	}
+
 	private addReplElement(newElement: IReplElement): void {
-		this.replElements.push(newElement);
-		if (this.replElements.length > MAX_REPL_LENGTH) {
-			this.replElements.splice(0, this.replElements.length - MAX_REPL_LENGTH);
+		const lastElement = this.replElements.length ? this.replElements[this.replElements.length - 1] : undefined;
+		if (lastElement instanceof ReplGroup && !lastElement.hasEnded) {
+			lastElement.addChild(newElement);
+		} else {
+			this.replElements.push(newElement);
+			if (this.replElements.length > MAX_REPL_LENGTH) {
+				this.replElements.splice(0, this.replElements.length - MAX_REPL_LENGTH);
+			}
 		}
+
 		this._onDidChangeElements.fire();
 	}
 
diff --git a/src/vs/workbench/contrib/debug/test/browser/repl.test.ts b/src/vs/workbench/contrib/debug/test/browser/repl.test.ts
index 297496be06471..1356848adc34c 100644
--- a/src/vs/workbench/contrib/debug/test/browser/repl.test.ts
+++ b/src/vs/workbench/contrib/debug/test/browser/repl.test.ts
@@ -8,7 +8,7 @@ import * as assert from 'assert';
 import severity from 'vs/base/common/severity';
 import { DebugModel, StackFrame, Thread } from 'vs/workbench/contrib/debug/common/debugModel';
 import { MockRawSession, MockDebugAdapter } from 'vs/workbench/contrib/debug/test/common/mockDebug';
-import { SimpleReplElement, RawObjectReplElement, ReplEvaluationInput, ReplModel, ReplEvaluationResult } from 'vs/workbench/contrib/debug/common/replModel';
+import { SimpleReplElement, RawObjectReplElement, ReplEvaluationInput, ReplModel, ReplEvaluationResult, ReplGroup } from 'vs/workbench/contrib/debug/common/replModel';
 import { RawDebugSession } from 'vs/workbench/contrib/debug/browser/rawDebugSession';
 import { timeout } from 'vs/base/common/async';
 import { createMockSession } from 'vs/workbench/contrib/debug/test/browser/callStack.test';
@@ -151,4 +151,42 @@ suite('Debug - REPL', () => {
 		assert.equal((<ReplEvaluationResult>session.getReplElements()[4]).value, '=after.2');
 		assert.equal((<SimpleReplElement>session.getReplElements()[5]).value, 'after.2');
 	});
+
+	test('repl groups', async () => {
+		const session = createMockSession(model);
+		const repl = new ReplModel();
+
+		repl.appendToRepl(session, 'first global line', severity.Info);
+		repl.startGroup('group_1', true);
+		repl.appendToRepl(session, 'first line in group', severity.Info);
+		repl.appendToRepl(session, 'second line in group', severity.Info);
+		const elements = repl.getReplElements();
+		assert.equal(elements.length, 2);
+		const group = elements[1] as ReplGroup;
+		assert.equal(group.name, 'group_1');
+		assert.equal(group.autoExpand, true);
+		assert.equal(group.hasChildren, true);
+		assert.equal(group.hasEnded, false);
+
+		repl.startGroup('group_2', false);
+		repl.appendToRepl(session, 'first line in subgroup', severity.Info);
+		repl.appendToRepl(session, 'second line in subgroup', severity.Info);
+		const children = group.getChildren();
+		assert.equal(children.length, 3);
+		assert.equal((<SimpleReplElement>children[0]).value, 'first line in group');
+		assert.equal((<SimpleReplElement>children[1]).value, 'second line in group');
+		assert.equal((<ReplGroup>children[2]).name, 'group_2');
+		assert.equal((<ReplGroup>children[2]).hasEnded, false);
+		assert.equal((<ReplGroup>children[2]).getChildren().length, 2);
+		repl.endGroup();
+		assert.equal((<ReplGroup>children[2]).hasEnded, true);
+		repl.appendToRepl(session, 'third line in group', severity.Info);
+		assert.equal(group.getChildren().length, 4);
+		assert.equal(group.hasEnded, false);
+		repl.endGroup();
+		assert.equal(group.hasEnded, true);
+		repl.appendToRepl(session, 'second global line', severity.Info);
+		assert.equal(repl.getReplElements().length, 3);
+		assert.equal((<SimpleReplElement>repl.getReplElements()[2]).value, 'second global line');
+	});
 });