diff --git a/src/vs/workbench/contrib/debug/browser/repl.ts b/src/vs/workbench/contrib/debug/browser/repl.ts
index a65674a80f96a..b12c97f0b8f54 100644
--- a/src/vs/workbench/contrib/debug/browser/repl.ts
+++ b/src/vs/workbench/contrib/debug/browser/repl.ts
@@ -19,13 +19,14 @@ import { HistoryNavigator } from 'vs/base/common/history';
 import { KeyCode, KeyMod } from 'vs/base/common/keyCodes';
 import { Disposable, IDisposable } from 'vs/base/common/lifecycle';
 import { removeAnsiEscapeCodes } from 'vs/base/common/strings';
+import { ThemeIcon } from 'vs/base/common/themables';
 import { URI as uri } from 'vs/base/common/uri';
 import 'vs/css!./media/repl';
 import { ICodeEditor, isCodeEditor } from 'vs/editor/browser/editorBrowser';
 import { EditorAction, registerEditorAction } from 'vs/editor/browser/editorExtensions';
 import { ICodeEditorService } from 'vs/editor/browser/services/codeEditorService';
 import { CodeEditorWidget } from 'vs/editor/browser/widget/codeEditorWidget';
-import { EditorOption, EDITOR_FONT_DEFAULTS } from 'vs/editor/common/config/editorOptions';
+import { EDITOR_FONT_DEFAULTS, EditorOption } from 'vs/editor/common/config/editorOptions';
 import { Position } from 'vs/editor/common/core/position';
 import { Range } from 'vs/editor/common/core/range';
 import { IDecorationOptions } from 'vs/editor/common/editorCommon';
@@ -55,7 +56,6 @@ import { IStorageService, StorageScope, StorageTarget } from 'vs/platform/storag
 import { ITelemetryService } from 'vs/platform/telemetry/common/telemetry';
 import { editorForeground, resolveColorValue } from 'vs/platform/theme/common/colorRegistry';
 import { IThemeService } from 'vs/platform/theme/common/themeService';
-import { ThemeIcon } from 'vs/base/common/themables';
 import { FilterViewPane, IViewPaneOptions, ViewAction } from 'vs/workbench/browser/parts/views/viewPane';
 import { IViewDescriptorService, IViewsService } from 'vs/workbench/common/views';
 import { getSimpleCodeEditorWidgetOptions, getSimpleEditorOptions } from 'vs/workbench/contrib/codeEditor/browser/simpleEditorOptions';
@@ -63,10 +63,10 @@ import { FocusSessionActionViewItem } from 'vs/workbench/contrib/debug/browser/d
 import { debugConsoleClearAll, debugConsoleEvaluationPrompt } from 'vs/workbench/contrib/debug/browser/debugIcons';
 import { LinkDetector } from 'vs/workbench/contrib/debug/browser/linkDetector';
 import { ReplFilter } from 'vs/workbench/contrib/debug/browser/replFilter';
-import { ReplAccessibilityProvider, ReplDataSource, ReplDelegate, ReplEvaluationInputsRenderer, ReplEvaluationResultsRenderer, ReplGroupRenderer, ReplRawObjectsRenderer, ReplOutputElementRenderer, ReplVariablesRenderer } from 'vs/workbench/contrib/debug/browser/replViewer';
-import { CONTEXT_DEBUG_STATE, CONTEXT_IN_DEBUG_REPL, CONTEXT_MULTI_SESSION_REPL, DEBUG_SCHEME, getStateLabel, IDebugConfiguration, IDebugService, IDebugSession, IReplConfiguration, IReplElement, IReplOptions, REPL_VIEW_ID, State } from 'vs/workbench/contrib/debug/common/debug';
+import { ReplAccessibilityProvider, ReplDataSource, ReplDelegate, ReplEvaluationInputsRenderer, ReplEvaluationResultsRenderer, ReplGroupRenderer, ReplOutputElementRenderer, ReplRawObjectsRenderer, ReplVariablesRenderer } from 'vs/workbench/contrib/debug/browser/replViewer';
+import { CONTEXT_DEBUG_STATE, CONTEXT_IN_DEBUG_REPL, CONTEXT_MULTI_SESSION_REPL, DEBUG_SCHEME, IDebugConfiguration, IDebugService, IDebugSession, IReplConfiguration, IReplElement, IReplOptions, REPL_VIEW_ID, State, getStateLabel } from 'vs/workbench/contrib/debug/common/debug';
 import { Variable } from 'vs/workbench/contrib/debug/common/debugModel';
-import { ReplGroup } from 'vs/workbench/contrib/debug/common/replModel';
+import { ReplEvaluationResult, ReplGroup } from 'vs/workbench/contrib/debug/common/replModel';
 import { IEditorService } from 'vs/workbench/services/editor/common/editorService';
 
 const $ = dom.$;
@@ -1045,12 +1045,33 @@ registerAction2(class extends Action2 {
 
 	async run(accessor: ServicesAccessor, element: IReplElement): Promise<void> {
 		const clipboardService = accessor.get(IClipboardService);
+		const debugService = accessor.get(IDebugService);
 		const nativeSelection = window.getSelection();
 		const selectedText = nativeSelection?.toString();
 		if (selectedText && selectedText.length > 0) {
-			await clipboardService.writeText(selectedText);
+			return clipboardService.writeText(selectedText);
 		} else if (element) {
-			await clipboardService.writeText(element.toString());
+			return clipboardService.writeText(await this.tryEvaluateAndCopy(debugService, element) || element.toString());
+		}
+	}
+
+	private async tryEvaluateAndCopy(debugService: IDebugService, element: IReplElement): Promise<string | undefined> {
+		// todo: we should expand DAP to allow copying more types here (#187784)
+		if (!(element instanceof ReplEvaluationResult)) {
+			return;
+		}
+
+		const stackFrame = debugService.getViewModel().focusedStackFrame;
+		const session = debugService.getViewModel().focusedSession;
+		if (!stackFrame || !session || !session.capabilities.supportsClipboardContext) {
+			return;
+		}
+
+		try {
+			const evaluation = await session.evaluate(element.originalExpression, stackFrame.frameId, 'clipboard');
+			return evaluation?.body.result;
+		} catch (e) {
+			return;
 		}
 	}
 });
diff --git a/src/vs/workbench/contrib/debug/browser/replViewer.ts b/src/vs/workbench/contrib/debug/browser/replViewer.ts
index 4193677ab1ec9..1ba443a95f18a 100644
--- a/src/vs/workbench/contrib/debug/browser/replViewer.ts
+++ b/src/vs/workbench/contrib/debug/browser/replViewer.ts
@@ -239,14 +239,14 @@ export class ReplVariablesRenderer extends AbstractExpressionsRenderer<IExpressi
 
 	public renderElement(node: ITreeNode<IExpression | ReplVariableElement, FuzzyScore>, _index: number, data: IExpressionTemplateData): void {
 		const element = node.element;
-		super.renderExpressionElement(element instanceof ReplVariableElement ? element.expr : element, node, data);
+		super.renderExpressionElement(element instanceof ReplVariableElement ? element.expression : element, node, data);
 	}
 
 	protected renderExpression(expression: IExpression | ReplVariableElement, data: IExpressionTemplateData, highlights: IHighlight[]): void {
 		const isReplVariable = expression instanceof ReplVariableElement;
 		if (isReplVariable || !expression.name) {
 			data.label.set('');
-			renderExpressionValue(isReplVariable ? expression.expr : expression, data.value, { showHover: false, colorize: true, linkDetector: this.linkDetector });
+			renderExpressionValue(isReplVariable ? expression.expression : expression, data.value, { showHover: false, colorize: true, linkDetector: this.linkDetector });
 			data.expression.classList.remove('nested-variable');
 		} else {
 			renderVariable(expression as Variable, data, true, highlights, this.linkDetector);
diff --git a/src/vs/workbench/contrib/debug/common/replModel.ts b/src/vs/workbench/contrib/debug/common/replModel.ts
index 9e28f1d66d18d..4402ed3f3b5c9 100644
--- a/src/vs/workbench/contrib/debug/common/replModel.ts
+++ b/src/vs/workbench/contrib/debug/common/replModel.ts
@@ -76,19 +76,19 @@ export class ReplVariableElement implements INestingReplElement {
 	private readonly id = generateUuid();
 
 	constructor(
-		public readonly expr: IExpression,
+		public readonly expression: IExpression,
 		public readonly severity: severity,
 		public readonly sourceData?: IReplElementSource,
 	) {
-		this.hasChildren = expr.hasChildren;
+		this.hasChildren = expression.hasChildren;
 	}
 
 	getChildren(): IReplElement[] | Promise<IReplElement[]> {
-		return this.expr.getChildren();
+		return this.expression.getChildren();
 	}
 
 	toString(): string {
-		return this.expr.toString();
+		return this.expression.toString();
 	}
 
 	getId(): string {
@@ -169,7 +169,7 @@ export class ReplEvaluationResult extends ExpressionContainer implements IReplEl
 		return this._available;
 	}
 
-	constructor() {
+	constructor(public readonly originalExpression: string) {
 		super(undefined, undefined, 0, generateUuid());
 	}
 
@@ -271,7 +271,7 @@ export class ReplModel {
 
 	async addReplExpression(session: IDebugSession, stackFrame: IStackFrame | undefined, name: string): Promise<void> {
 		this.addReplElement(new ReplEvaluationInput(name));
-		const result = new ReplEvaluationResult();
+		const result = new ReplEvaluationResult(name);
 		await result.evaluateExpression(name, session, stackFrame, 'repl');
 		this.addReplElement(result);
 	}
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 276f3e74aecfc..a04f2ed196330 100644
--- a/src/vs/workbench/contrib/debug/test/browser/repl.test.ts
+++ b/src/vs/workbench/contrib/debug/test/browser/repl.test.ts
@@ -51,8 +51,8 @@ suite('Debug - REPL', () => {
 		const keyValueObject = { 'key1': 2, 'key2': 'value' };
 		repl.appendToRepl(session, { output: '', expression: new RawObjectReplElement('fakeid', 'fake', keyValueObject), sev: severity.Info });
 		const element = <ReplVariableElement>repl.getReplElements()[3];
-		assert.strictEqual(element.expr.value, 'Object');
-		assert.deepStrictEqual((element.expr as RawObjectReplElement).valueObj, keyValueObject);
+		assert.strictEqual(element.expression.value, 'Object');
+		assert.deepStrictEqual((element.expression as RawObjectReplElement).valueObj, keyValueObject);
 
 		repl.removeReplExpressions();
 		assert.strictEqual(repl.getReplElements().length, 0);