diff --git a/src/vs/workbench/services/dialogs/browser/simpleFileDialog.ts b/src/vs/workbench/services/dialogs/browser/simpleFileDialog.ts
index e85ce241236b9b..afd0396836e26f 100644
--- a/src/vs/workbench/services/dialogs/browser/simpleFileDialog.ts
+++ b/src/vs/workbench/services/dialogs/browser/simpleFileDialog.ts
@@ -912,8 +912,13 @@ export class SimpleFileDialog extends Disposable implements ISimpleFileDialog {
 			disposableStore.add(prompt.onDidHide(() => {
 				if (!isResolving) {
 					resolve(false);
+					this.filePickBox.show();
+					// The quick pick UI's list is shared between quick picks, so showing the
+					// yes/no prompt above replaced the items in the underlying list. Re-assign
+					// the items so they are rendered again when the file picker is shown.
+					const currentItems = this.filePickBox.items;
+					this.filePickBox.items = currentItems;
 				}
-				this.filePickBox.show();
 				this.hidden = false;
 				disposableStore.dispose();
 			}));