diff --git a/apps/web/src/components/chat/workspaceFileDrop.test.ts b/apps/web/src/components/chat/workspaceFileDrop.test.ts
index ec5d074a3eb7..3a81e35c2a2d 100644
--- a/apps/web/src/components/chat/workspaceFileDrop.test.ts
+++ b/apps/web/src/components/chat/workspaceFileDrop.test.ts
@@ -8,6 +8,7 @@ import {
 function makeDragEvent(options?: {
   types?: string[];
   files?: File[];
+  items?: NonNullable<WorkspaceFileDragEvent["dataTransfer"]["items"]>;
   movedWithinTarget?: boolean;
 }) {
   const preventDefault = vi.fn();
@@ -16,6 +17,7 @@ function makeDragEvent(options?: {
       types: options?.types ?? ["Files"],
       files: options?.files ?? [],
       dropEffect: "none",
+      ...(options?.items === undefined ? {} : { items: options.items }),
     },
     relatedTarget: options?.movedWithinTarget ? ({} as EventTarget) : null,
     currentTarget: {
@@ -75,4 +77,42 @@ describe("makeWorkspaceFileDropHandlers", () => {
     expect(setDragActive).toHaveBeenCalledWith(false);
     expect(addFiles).toHaveBeenCalledWith([file]);
   });
+
+  it("skips dropped directories in mixed drops", () => {
+    const file = new File(["contents"], "example.txt", { type: "text/plain" });
+    const directory = {
+      kind: "file",
+      getAsFile: () => null,
+      webkitGetAsEntry: () => ({ isDirectory: true }),
+    };
+    const { host, addFiles } = makeHost();
+    const { event } = makeDragEvent({
+      items: [
+        directory,
+        {
+          kind: "file",
+          getAsFile: () => file,
+          webkitGetAsEntry: () => ({ isDirectory: false }),
+        },
+      ],
+    });
+
+    makeWorkspaceFileDropHandlers(host).onDrop(event);
+
+    expect(addFiles).toHaveBeenCalledWith([file]);
+  });
+
+  it("passes an empty list when a drop only contains a directory", () => {
+    const directory = {
+      kind: "file",
+      getAsFile: () => null,
+      webkitGetAsEntry: () => ({ isDirectory: true }),
+    };
+    const { host, addFiles } = makeHost();
+    const { event } = makeDragEvent({ items: [directory] });
+
+    makeWorkspaceFileDropHandlers(host).onDrop(event);
+
+    expect(addFiles).toHaveBeenCalledWith([]);
+  });
 });
diff --git a/apps/web/src/components/chat/workspaceFileDrop.ts b/apps/web/src/components/chat/workspaceFileDrop.ts
index 132a8051e159..3e6dbf3570f4 100644
--- a/apps/web/src/components/chat/workspaceFileDrop.ts
+++ b/apps/web/src/components/chat/workspaceFileDrop.ts
@@ -2,6 +2,11 @@ export interface WorkspaceFileDragEvent {
   readonly dataTransfer: {
     readonly types: ReadonlyArray<string>;
     readonly files: Iterable<File>;
+    readonly items?: Iterable<{
+      readonly kind: string;
+      getAsFile(): File | null;
+      webkitGetAsEntry(): { readonly isDirectory: boolean } | null;
+    }>;
     dropEffect: string;
   };
   readonly relatedTarget: EventTarget | null;
@@ -24,6 +29,18 @@ function movedWithinDropTarget(event: WorkspaceFileDragEvent): boolean {
   return event.relatedTarget !== null && event.currentTarget.contains(event.relatedTarget as Node);
 }
 
+function droppedFiles(dataTransfer: WorkspaceFileDragEvent["dataTransfer"]): File[] {
+  if (dataTransfer.items === undefined) return Array.from(dataTransfer.files);
+
+  const files: File[] = [];
+  for (const item of dataTransfer.items) {
+    if (item.kind !== "file" || item.webkitGetAsEntry()?.isDirectory === true) continue;
+    const file = item.getAsFile();
+    if (file !== null) files.push(file);
+  }
+  return files;
+}
+
 export function makeWorkspaceFileDropHandlers(host: WorkspaceFileDropHost) {
   return {
     onDragEnter(event: WorkspaceFileDragEvent) {
@@ -48,7 +65,7 @@ export function makeWorkspaceFileDropHandlers(host: WorkspaceFileDropHost) {
       if (!isFileDrag(event)) return;
       event.preventDefault();
       host.setDragActive(false);
-      host.addFiles(Array.from(event.dataTransfer.files));
+      host.addFiles(droppedFiles(event.dataTransfer));
     },
   };
 }