diff --git a/src/vs/workbench/parts/debug/electron-browser/repl.ts b/src/vs/workbench/parts/debug/electron-browser/repl.ts
index 8574e52a10eb4d2e34c4c4bfdd4673d3096d1033..bb1122bc2f26bcebe97af929df3ac694c1bc3d35 100644
--- a/src/vs/workbench/parts/debug/electron-browser/repl.ts
+++ b/src/vs/workbench/parts/debug/electron-browser/repl.ts
@@ -24,7 +24,7 @@ import { registerEditorAction, ServicesAccessor, EditorAction, EditorCommand, re
 import { IModelService } from 'vs/editor/common/services/modelService';
 import { MenuId } from 'vs/platform/actions/common/actions';
 import { ServiceCollection } from 'vs/platform/instantiation/common/serviceCollection';
-import { IContextKeyService, ContextKeyExpr } from 'vs/platform/contextkey/common/contextkey';
+import { IContextKeyService, ContextKeyExpr, IContextKey } from 'vs/platform/contextkey/common/contextkey';
 import { ITelemetryService } from 'vs/platform/telemetry/common/telemetry';
 import { IInstantiationService, createDecorator } from 'vs/platform/instantiation/common/instantiation';
 import { IStorageService, StorageScope } from 'vs/platform/storage/common/storage';
@@ -84,6 +84,7 @@ export class Repl extends Panel implements IPrivateReplService, IHistoryNavigati
 	private dimension: dom.Dimension;
 	private replInputHeight: number;
 	private model: ITextModel;
+	private historyNavigationEnablement: IContextKey<boolean>;
 
 	constructor(
 		@IDebugService private debugService: IDebugService,
@@ -164,6 +165,7 @@ export class Repl extends Panel implements IPrivateReplService, IHistoryNavigati
 		this.replInputContainer = dom.append(container, $('.repl-input-wrapper'));
 
 		const { scopedContextKeyService, historyNavigationEnablement } = createAndBindHistoryNavigationWidgetScopedContextKeyService(this.contextKeyService, { target: this.replInputContainer, historyNavigator: this });
+		this.historyNavigationEnablement = historyNavigationEnablement;
 		this.toUnbind.push(scopedContextKeyService);
 		CONTEXT_IN_DEBUG_REPL.bindTo(scopedContextKeyService).set(true);
 
@@ -175,7 +177,7 @@ export class Repl extends Panel implements IPrivateReplService, IHistoryNavigati
 			triggerCharacters: ['.'],
 			provideCompletionItems: (model: ITextModel, position: Position, _context: modes.SuggestContext, token: CancellationToken): Thenable<modes.ISuggestResult> => {
 				// Disable history navigation because up and down are used to navigate through the suggest widget
-				historyNavigationEnablement.set(false);
+				this.historyNavigationEnablement.set(false);
 				const word = this.replInput.getModel().getWordAtPosition(position);
 				const overwriteBefore = word ? word.word.length : 0;
 				const text = this.replInput.getModel().getLineContent(position.lineNumber);
@@ -197,7 +199,7 @@ export class Repl extends Panel implements IPrivateReplService, IHistoryNavigati
 			this.layout(this.dimension);
 		}));
 		this.toUnbind.push(this.replInput.onDidChangeModelContent(() => {
-			historyNavigationEnablement.set(this.replInput.getModel().getLineCount() === 1);
+			this.historyNavigationEnablement.set(this.replInput.getModel().getValue() === '');
 		}));
 
 		this.toUnbind.push(dom.addStandardDisposableListener(this.replInputContainer, dom.EventType.FOCUS, () => dom.addClass(this.replInputContainer, 'synthetic-focus')));
@@ -210,6 +212,7 @@ export class Repl extends Panel implements IPrivateReplService, IHistoryNavigati
 			this.replInput.setValue(historyInput);
 			// always leave cursor at the end.
 			this.replInput.setPosition({ lineNumber: 1, column: historyInput.length + 1 });
+			this.historyNavigationEnablement.set(true);
 		}
 	}