diff --git a/src/vs/workbench/parts/debug/common/debug.ts b/src/vs/workbench/parts/debug/common/debug.ts
index 6d05e411b14d4..7b6338bcad8e8 100644
--- a/src/vs/workbench/parts/debug/common/debug.ts
+++ b/src/vs/workbench/parts/debug/common/debug.ts
@@ -36,9 +36,9 @@ export const BREAKPOINTS_VIEW_ID = 'workbench.debug.breakPointsView';
 export const REPL_ID = 'workbench.panel.repl';
 export const DEBUG_SERVICE_ID = 'debugService';
 export const CONTEXT_DEBUG_TYPE = new RawContextKey<string>('debugType', undefined);
-export const CONTEXT_DEBUG_STATE = new RawContextKey<string>('debugState', undefined);
-export const CONTEXT_IN_DEBUG_MODE = new RawContextKey<boolean>('inDebugMode', false);
-export const CONTEXT_NOT_IN_DEBUG_MODE: ContextKeyExpr = CONTEXT_IN_DEBUG_MODE.toNegated();
+export const CONTEXT_DEBUG_STATE = new RawContextKey<string>('debugState', 'inactive');
+export const CONTEXT_NOT_IN_DEBUG_MODE = CONTEXT_DEBUG_STATE.isEqualTo('inactive');
+export const CONTEXT_IN_DEBUG_MODE = CONTEXT_DEBUG_STATE.notEqualsTo('inactive');
 export const CONTEXT_IN_DEBUG_REPL = new RawContextKey<boolean>('inDebugRepl', false);
 export const CONTEXT_NOT_IN_DEBUG_REPL: ContextKeyExpr = CONTEXT_IN_DEBUG_REPL.toNegated();
 export const CONTEXT_BREAKPOINT_WIDGET_VISIBLE = new RawContextKey<boolean>('breakpointWidgetVisible', false);
diff --git a/src/vs/workbench/parts/debug/electron-browser/debugService.ts b/src/vs/workbench/parts/debug/electron-browser/debugService.ts
index bc11ac3f751e9..637e1aed9df21 100644
--- a/src/vs/workbench/parts/debug/electron-browser/debugService.ts
+++ b/src/vs/workbench/parts/debug/electron-browser/debugService.ts
@@ -76,7 +76,6 @@ export class DebugService implements debug.IDebugService {
 	private configurationManager: ConfigurationManager;
 	private toDispose: lifecycle.IDisposable[];
 	private toDisposeOnSessionEnd: Map<string, lifecycle.IDisposable[]>;
-	private inDebugMode: IContextKey<boolean>;
 	private debugType: IContextKey<string>;
 	private debugState: IContextKey<string>;
 	private breakpointsToSendOnResourceSaved: Set<string>;
@@ -120,7 +119,6 @@ export class DebugService implements debug.IDebugService {
 
 		this.configurationManager = this.instantiationService.createInstance(ConfigurationManager);
 		this.toDispose.push(this.configurationManager);
-		this.inDebugMode = debug.CONTEXT_IN_DEBUG_MODE.bindTo(contextKeyService);
 		this.debugType = debug.CONTEXT_DEBUG_TYPE.bindTo(contextKeyService);
 		this.debugState = debug.CONTEXT_DEBUG_STATE.bindTo(contextKeyService);
 
@@ -909,7 +907,6 @@ export class DebugService implements debug.IDebugService {
 
 		const resolved = configuration.resolved;
 		resolved.__sessionId = sessionId;
-		this.inDebugMode.set(true);
 
 		const dbg = this.configurationManager.getDebugger(resolved.type);
 		return this.initializeRawSession(root, configuration, sessionId).then(session => {
@@ -985,9 +982,6 @@ export class DebugService implements debug.IDebugService {
 					if (this.model.getReplElements().length > 0) {
 						this.panelService.openPanel(debug.REPL_ID, false).done(undefined, errors.onUnexpectedError);
 					}
-					if (this.model.getSessions().length === 0) {
-						this.inDebugMode.reset();
-					}
 
 					this.showError(errorMessage, errors.isErrorWithActions(error) ? error.actions : []);
 					return undefined;
@@ -1209,7 +1203,6 @@ export class DebugService implements debug.IDebugService {
 		this.updateStateAndEmit(raw.getId(), debug.State.Inactive);
 
 		if (this.model.getSessions().length === 0) {
-			this.inDebugMode.reset();
 			this.debugType.reset();
 			this.viewModel.setMultiSessionView(false);