diff --git a/src/vs/workbench/browser/parts/compositeBar.ts b/src/vs/workbench/browser/parts/compositeBar.ts
index 5e83a9458bdf7..11577775c8e39 100644
--- a/src/vs/workbench/browser/parts/compositeBar.ts
+++ b/src/vs/workbench/browser/parts/compositeBar.ts
@@ -267,6 +267,10 @@ export class CompositeBar extends Widget implements ICompositeBar {
 		return this.model.pinnedItems;
 	}
 
+	getPinnedCompositeIds(): string[] {
+		return this.getPinnedComposites().map(c => c.id);
+	}
+
 	getVisibleComposites(): ICompositeBarItem[] {
 		return this.model.visibleItems;
 	}
@@ -651,19 +655,22 @@ export class CompositeBar extends Widget implements ICompositeBar {
 
 	getContextMenuActions(e?: MouseEvent | GestureEvent): IAction[] {
 		const actions: IAction[] = this.model.visibleItems
-			.map(({ id, name, activityAction }) => (toAction({
-				id,
-				label: this.getAction(id).label || name || id,
-				checked: this.isPinned(id),
-				enabled: activityAction.enabled,
-				run: () => {
-					if (this.isPinned(id)) {
-						this.unpin(id);
-					} else {
-						this.pin(id, true);
+			.map(({ id, name, activityAction }) => {
+				const isPinned = this.isPinned(id);
+				return toAction({
+					id,
+					label: this.getAction(id).label || name || id,
+					checked: isPinned,
+					enabled: activityAction.enabled && (!isPinned || this.getPinnedCompositeIds().length > 1),
+					run: () => {
+						if (this.isPinned(id)) {
+							this.unpin(id);
+						} else {
+							this.pin(id, true);
+						}
 					}
-				}
-			})));
+				});
+			});
 
 		this.options.fillExtraContextMenuActions(actions, e);
 
diff --git a/src/vs/workbench/browser/parts/compositeBarActions.ts b/src/vs/workbench/browser/parts/compositeBarActions.ts
index 15f6b06331c8e..89876b6dffc61 100644
--- a/src/vs/workbench/browser/parts/compositeBarActions.ts
+++ b/src/vs/workbench/browser/parts/compositeBarActions.ts
@@ -45,6 +45,11 @@ export interface ICompositeBar {
 	 */
 	isPinned(compositeId: string): boolean;
 
+	/**
+	 * Get pinned composite ids in the composite bar.
+	 */
+	getPinnedCompositeIds(): string[];
+
 	/**
 	 * Returns if badges are enabled for that specified composite.
 	 * @param compositeId The id of the composite to check
@@ -689,8 +694,10 @@ export class CompositeActionViewItem extends CompositeBarActionViewItem {
 		if (isPinned) {
 			this.toggleCompositePinnedAction.label = localize('hide', "Hide '{0}'", this.compositeBarActionItem.name);
 			this.toggleCompositePinnedAction.checked = false;
+			this.toggleCompositePinnedAction.enabled = this.compositeBar.getPinnedCompositeIds().length > 1;
 		} else {
 			this.toggleCompositePinnedAction.label = localize('keep', "Keep '{0}'", this.compositeBarActionItem.name);
+			this.toggleCompositePinnedAction.enabled = true;
 		}
 
 		const isBadgeEnabled = this.compositeBar.areBadgesEnabled(this.compositeBarActionItem.id);