diff --git a/ui/src/components/WorkFolderBrowser.selection.test.tsx b/ui/src/components/WorkFolderBrowser.selection.test.tsx
index dd3e5baa43..6ce77a3971 100644
--- a/ui/src/components/WorkFolderBrowser.selection.test.tsx
+++ b/ui/src/components/WorkFolderBrowser.selection.test.tsx
@@ -99,13 +99,13 @@ describe("cached file selection and retained trash", () => {
     expect(checkbox("a.txt")).not.toBeNull();
     expect(deleted).toEqual([]);
   });
-  it("refreshes partial successes and leaves only failed files selected for retry", async () => {
+  it.each([["a.txt", "b.txt"], ["b.txt", "a.txt"]])("refreshes partial successes when selected in order %s, %s", async (first, second) => {
     const operate = api.operation.getMockImplementation()!;
     api.operation.mockImplementation(async (target, operation) => {
       if (operation.path === "b.txt") throw new Error("Storage unavailable");
       return operate(target, operation);
     });
-    await click(checkbox("a.txt")); await click(checkbox("b.txt"));
+    await click(checkbox(first)); await click(checkbox(second));
     await click(button("Move 2 files to trash")!);
     expect(checkbox("a.txt")).toBeNull();
     expect(checkbox("b.txt").checked).toBe(true);
diff --git a/ui/src/components/WorkFolderBrowser.tsx b/ui/src/components/WorkFolderBrowser.tsx
index f6015f9ce2..5ab993f68e 100644
--- a/ui/src/components/WorkFolderBrowser.tsx
+++ b/ui/src/components/WorkFolderBrowser.tsx
@@ -69,11 +69,17 @@ export function WorkFolderBrowser({ owner, exampleFiles, readOnly = false, fillH
     if (action.type === "upload") for (const file of action.files) await workFoldersApi.upload(owner, file, directory ? `${directory}/${file.name}` : file.name, crypto.randomUUID());
     else if (action.type === "mkdir") { await workFoldersApi.operation(owner, { action: "mkdir", path: directory }, crypto.randomUUID()); setExpanded((before) => new Set([...before, directory])); }
     else if (action.type === "deleteSelected") {
+      const failures: string[] = [];
       for (const path of action.paths) {
-        await workFoldersApi.operation(owner, { action: "delete", path }, crypto.randomUUID());
-        setCheckedFiles((before) => new Set([...before].filter((candidate) => candidate !== path && !candidate.startsWith(`${path}/`))));
-        setSelectedPath((before) => before === path || before?.startsWith(`${path}/`) ? null : before);
+        try {
+          await workFoldersApi.operation(owner, { action: "delete", path }, crypto.randomUUID());
+          setCheckedFiles((before) => new Set([...before].filter((candidate) => candidate !== path && !candidate.startsWith(`${path}/`))));
+          setSelectedPath((before) => before === path || before?.startsWith(`${path}/`) ? null : before);
+        } catch (error) {
+          failures.push(`${path}: ${error instanceof Error ? error.message : "Could not move to trash"}`);
+        }
       }
+      if (failures.length > 0) throw new Error(failures.join("; "));
     }
     else if (action.type === "restore" || action.type === "purge") await workFoldersApi.operation(owner, { action: action.type, fileId: action.fileId }, crypto.randomUUID());
     else for (const run of (syncQuery.data ?? []).filter((run) => run.active)) await workFoldersApi.refresh(owner, run.runId);