diff --git a/src/vs/workbench/contrib/files/browser/fileActions.contribution.ts b/src/vs/workbench/contrib/files/browser/fileActions.contribution.ts
index b1f2f64fa31d35859f2867785602a76aeb9f12ee..aabb8afd4afb66a94e0133ec5f9c0c65e349917d 100644
--- a/src/vs/workbench/contrib/files/browser/fileActions.contribution.ts
+++ b/src/vs/workbench/contrib/files/browser/fileActions.contribution.ts
@@ -77,7 +77,7 @@ const MOVE_FILE_TO_TRASH_ID = 'moveFileToTrash';
 KeybindingsRegistry.registerCommandAndKeybindingRule({
 	id: MOVE_FILE_TO_TRASH_ID,
 	weight: KeybindingWeight.WorkbenchContrib + explorerCommandsWeightBonus,
-	when: ContextKeyExpr.and(FilesExplorerFocusCondition, ExplorerRootContext.toNegated(), ExplorerResourceNotReadonlyContext, ExplorerResourceMoveableToTrash),
+	when: ContextKeyExpr.and(FilesExplorerFocusCondition, ExplorerResourceNotReadonlyContext, ExplorerResourceMoveableToTrash),
 	primary: KeyCode.Delete,
 	mac: {
 		primary: KeyMod.CtrlCmd | KeyCode.Backspace
@@ -89,7 +89,7 @@ const DELETE_FILE_ID = 'deleteFile';
 KeybindingsRegistry.registerCommandAndKeybindingRule({
 	id: DELETE_FILE_ID,
 	weight: KeybindingWeight.WorkbenchContrib + explorerCommandsWeightBonus,
-	when: ContextKeyExpr.and(FilesExplorerFocusCondition, ExplorerRootContext.toNegated(), ExplorerResourceNotReadonlyContext),
+	when: ContextKeyExpr.and(FilesExplorerFocusCondition, ExplorerResourceNotReadonlyContext),
 	primary: KeyMod.Shift | KeyCode.Delete,
 	mac: {
 		primary: KeyMod.CtrlCmd | KeyMod.Alt | KeyCode.Backspace
@@ -100,7 +100,7 @@ KeybindingsRegistry.registerCommandAndKeybindingRule({
 KeybindingsRegistry.registerCommandAndKeybindingRule({
 	id: DELETE_FILE_ID,
 	weight: KeybindingWeight.WorkbenchContrib + explorerCommandsWeightBonus,
-	when: ContextKeyExpr.and(FilesExplorerFocusCondition, ExplorerRootContext.toNegated(), ExplorerResourceNotReadonlyContext, ExplorerResourceMoveableToTrash.toNegated()),
+	when: ContextKeyExpr.and(FilesExplorerFocusCondition, ExplorerResourceNotReadonlyContext, ExplorerResourceMoveableToTrash.toNegated()),
 	primary: KeyCode.Delete,
 	mac: {
 		primary: KeyMod.CtrlCmd | KeyCode.Backspace
diff --git a/src/vs/workbench/contrib/files/browser/fileActions.ts b/src/vs/workbench/contrib/files/browser/fileActions.ts
index b21409c7e6318cb00e241f40ffa42eb133693a26..0e1d4b4801acdee094e0270ec57521379b0a172e 100644
--- a/src/vs/workbench/contrib/files/browser/fileActions.ts
+++ b/src/vs/workbench/contrib/files/browser/fileActions.ts
@@ -937,17 +937,21 @@ export const renameHandler = (accessor: ServicesAccessor) => {
 	});
 };
 
-export const moveFileToTrashHandler = (accessor: ServicesAccessor) => {
+export const moveFileToTrashHandler = async (accessor: ServicesAccessor) => {
 	const explorerService = accessor.get(IExplorerService);
-	const stats = explorerService.getContext(true);
-	return deleteFiles(accessor.get(ITextFileService), accessor.get(IDialogService), accessor.get(IConfigurationService), accessor.get(IFileService), stats, true);
+	const stats = explorerService.getContext(true).filter(s => !s.isRoot);
+	if (stats.length) {
+		await deleteFiles(accessor.get(ITextFileService), accessor.get(IDialogService), accessor.get(IConfigurationService), accessor.get(IFileService), stats, true);
+	}
 };
 
-export const deleteFileHandler = (accessor: ServicesAccessor) => {
+export const deleteFileHandler = async (accessor: ServicesAccessor) => {
 	const explorerService = accessor.get(IExplorerService);
-	const stats = explorerService.getContext(true);
+	const stats = explorerService.getContext(true).filter(s => !s.isRoot);
 
-	return deleteFiles(accessor.get(ITextFileService), accessor.get(IDialogService), accessor.get(IConfigurationService), accessor.get(IFileService), stats, false);
+	if (stats.length) {
+		await deleteFiles(accessor.get(ITextFileService), accessor.get(IDialogService), accessor.get(IConfigurationService), accessor.get(IFileService), stats, false);
+	}
 };
 
 let pasteShouldMove = false;
diff --git a/src/vs/workbench/contrib/files/browser/views/explorerView.ts b/src/vs/workbench/contrib/files/browser/views/explorerView.ts
index 9d585d6d276e431c6c91abc06493d7d0b6e3ba6d..050e0a9f8c791d89fac9a665660f1fc28c378ebe 100644
--- a/src/vs/workbench/contrib/files/browser/views/explorerView.ts
+++ b/src/vs/workbench/contrib/files/browser/views/explorerView.ts
@@ -293,10 +293,6 @@ export class ExplorerView extends ViewletPanel {
 			focusedStat = focus.length ? focus[0] : undefined;
 		}
 
-		if (!focusedStat) {
-			return [];
-		}
-
 		const selectedStats: ExplorerItem[] = [];
 
 		for (const stat of this.tree.getSelection()) {
@@ -308,6 +304,13 @@ export class ExplorerView extends ViewletPanel {
 				selectedStats.push(stat);
 			}
 		}
+		if (!focusedStat) {
+			if (respectMultiSelection) {
+				return selectedStats;
+			} else {
+				return [];
+			}
+		}
 
 		if (respectMultiSelection && selectedStats.indexOf(focusedStat) >= 0) {
 			return selectedStats;