fixes #53240

src/vs/platform/list/browser/listService.ts

@@ -102,11 +102,6 @@ export const WorkbenchListMultiSelection = new RawContextKey<boolean>('listMulti
 
 function createScopedContextKeyService(contextKeyService: IContextKeyService, widget: ListWidget): IContextKeyService {
 	const result = contextKeyService.createScoped(widget.getHTMLElement());
-
-	if (widget instanceof List || widget instanceof PagedList) {
-		WorkbenchListSupportsMultiSelectContextKey.bindTo(result);
-	}
-
 	RawWorkbenchListFocusContextKey.bindTo(result);
 	return result;
 }
@@ -233,6 +228,10 @@ export class WorkbenchList<T> extends List<T> {
 		);
 
 		this.contextKeyService = createScopedContextKeyService(contextKeyService, this);
+
+		const listSupportsMultiSelect = WorkbenchListSupportsMultiSelectContextKey.bindTo(this.contextKeyService);
+		listSupportsMultiSelect.set(!(options.multipleSelectionSupport === false));
+
 		this.listHasSelectionOrFocus = WorkbenchListHasSelectionOrFocus.bindTo(this.contextKeyService);
 		this.listDoubleSelection = WorkbenchListDoubleSelection.bindTo(this.contextKeyService);
 		this.listMultiSelection = WorkbenchListMultiSelection.bindTo(this.contextKeyService);
@@ -305,6 +304,9 @@ export class WorkbenchPagedList<T> extends PagedList<T> {
 
 		this.contextKeyService = createScopedContextKeyService(contextKeyService, this);
 
+		const listSupportsMultiSelect = WorkbenchListSupportsMultiSelectContextKey.bindTo(this.contextKeyService);
+		listSupportsMultiSelect.set(!(options.multipleSelectionSupport === false));
+
 		this._useAltAsMultipleSelectionModifier = useAltAsMultipleSelectionModifier(configurationService);
 
 		this.disposables.push(combinedDisposable([
@@ -371,6 +373,9 @@ export class WorkbenchTree extends Tree {
 
 		this.disposables = [];
 		this.contextKeyService = createScopedContextKeyService(contextKeyService, this);
+
+		WorkbenchListSupportsMultiSelectContextKey.bindTo(this.contextKeyService);
+
 		this.listHasSelectionOrFocus = WorkbenchListHasSelectionOrFocus.bindTo(this.contextKeyService);
 		this.listDoubleSelection = WorkbenchListDoubleSelection.bindTo(this.contextKeyService);
 		this.listMultiSelection = WorkbenchListMultiSelection.bindTo(this.contextKeyService);

src/vs/workbench/electron-browser/commands.ts

@@ -105,7 +105,7 @@ export function registerCommands(): void {
 	KeybindingsRegistry.registerCommandAndKeybindingRule({
 		id: 'list.expandSelectionDown',
 		weight: KeybindingsRegistry.WEIGHT.workbenchContrib(),
-		when: WorkbenchListFocusContextKey,
+		when: ContextKeyExpr.and(WorkbenchListFocusContextKey, WorkbenchListSupportsMultiSelectContextKey),
 		primary: KeyMod.Shift | KeyCode.DownArrow,
 		handler: (accessor, arg2) => {
 			const focused = accessor.get(IListService).lastFocusedList;
@@ -178,7 +178,7 @@ export function registerCommands(): void {
 	KeybindingsRegistry.registerCommandAndKeybindingRule({
 		id: 'list.expandSelectionUp',
 		weight: KeybindingsRegistry.WEIGHT.workbenchContrib(),
-		when: WorkbenchListFocusContextKey,
+		when: ContextKeyExpr.and(WorkbenchListFocusContextKey, WorkbenchListSupportsMultiSelectContextKey),
 		primary: KeyMod.Shift | KeyCode.UpArrow,
 		handler: (accessor, arg2) => {
 			const focused = accessor.get(IListService).lastFocusedList;