diff --git a/frontend/src/components/files/ListingItem.vue b/frontend/src/components/files/ListingItem.vue
index d6747f59..33b5a993 100644
--- a/frontend/src/components/files/ListingItem.vue
+++ b/frontend/src/components/files/ListingItem.vue
@@ -179,6 +179,7 @@ const drop = async (event: Event) => {
         to: props.url + encodeURIComponent(fileStore.req?.items[i].name),
         name: fileStore.req?.items[i].name,
         size: fileStore.req?.items[i].size,
+        isDir: fileStore.req?.items[i].isDir,
         modified: fileStore.req?.items[i].modified,
         overwrite: false,
         rename: false,
@@ -204,7 +205,7 @@ const drop = async (event: Event) => {
       .catch($showError);
   };
 
-  const conflict = await upload.checkConflict(items, path);
+  const conflict = await upload.checkConflict(items, path, true);
 
   if (conflict.length > 0) {
     layoutStore.showHover({
diff --git a/frontend/src/components/prompts/Copy.vue b/frontend/src/components/prompts/Copy.vue
index 0073df8d..37139b9b 100644
--- a/frontend/src/components/prompts/Copy.vue
+++ b/frontend/src/components/prompts/Copy.vue
@@ -123,7 +123,7 @@ export default {
           });
       };
 
-      const conflict = await upload.checkConflict(items, this.dest);
+      const conflict = await upload.checkConflict(items, this.dest, true);
 
       if (conflict.length > 0) {
         this.showHover({
diff --git a/frontend/src/components/prompts/Move.vue b/frontend/src/components/prompts/Move.vue
index 34a0d0fa..b8086a67 100644
--- a/frontend/src/components/prompts/Move.vue
+++ b/frontend/src/components/prompts/Move.vue
@@ -123,7 +123,7 @@ export default {
           });
       };
 
-      const conflict = await upload.checkConflict(items, this.dest);
+      const conflict = await upload.checkConflict(items, this.dest, true);
 
       if (conflict.length > 0) {
         this.showHover({
diff --git a/frontend/src/components/prompts/__tests__/copy-move-conflict.test.ts b/frontend/src/components/prompts/__tests__/copy-move-conflict.test.ts
index 8241be2e..cc138329 100644
--- a/frontend/src/components/prompts/__tests__/copy-move-conflict.test.ts
+++ b/frontend/src/components/prompts/__tests__/copy-move-conflict.test.ts
@@ -86,7 +86,8 @@ describe("copy and move conflict prompts", () => {
           isDir: false,
         }),
       ],
-      "/files/target/"
+      "/files/target/",
+      true
     );
     expect(context.showHover).toHaveBeenCalledWith(
       expect.objectContaining({
@@ -109,7 +110,8 @@ describe("copy and move conflict prompts", () => {
           isDir: false,
         }),
       ],
-      "/files/target/"
+      "/files/target/",
+      true
     );
     expect(context.showHover).toHaveBeenCalledWith(
       expect.objectContaining({
diff --git a/frontend/src/types/file.d.ts b/frontend/src/types/file.d.ts
index 7e6a9ebc..067598b0 100644
--- a/frontend/src/types/file.d.ts
+++ b/frontend/src/types/file.d.ts
@@ -53,6 +53,7 @@ interface ClipItem {
   from: string;
   name: string;
   size?: number;
+  isDir?: boolean;
   modified?: string;
 }
 
diff --git a/frontend/src/utils/__tests__/check-conflict.test.ts b/frontend/src/utils/__tests__/check-conflict.test.ts
index e73bd979..37a4e69b 100644
--- a/frontend/src/utils/__tests__/check-conflict.test.ts
+++ b/frontend/src/utils/__tests__/check-conflict.test.ts
@@ -167,6 +167,49 @@ describe("checkConflict", () => {
     expect(conflicts[0].name).toBe("/target/folder/deep/file.txt");
   });
 
+  // Copy/move stats the whole destination, so a same-named directory is a
+  // conflict in its own right (regression for the directory case of #5957).
+  it("reports a directory conflict for copy/move (includeDirectories)", async () => {
+    vi.mocked(api.fetchAll).mockResolvedValue([
+      {
+        path: "/target/folder",
+        name: "folder",
+        size: 0,
+        modified: "2026-06-04T00:00:00Z",
+        isDir: true,
+      },
+    ]);
+
+    const items = [{ ...moveItem("folder", "/files/target/", 0), isDir: true }];
+
+    const conflicts = await checkConflict(items, "/files/target/", true);
+
+    expect(conflicts).toHaveLength(1);
+    expect(conflicts[0].name).toBe("/target/folder");
+  });
+
+  // Uploads merge into an existing folder, so the directory itself must not be
+  // reported — only the files inside it can conflict.
+  it("ignores a directory conflict for uploads (default)", async () => {
+    vi.mocked(api.fetchAll).mockResolvedValue([
+      {
+        path: "/target/folder",
+        name: "folder",
+        size: 0,
+        modified: "2026-06-04T00:00:00Z",
+        isDir: true,
+      },
+    ]);
+
+    const files = [
+      { name: "folder", size: 0, isDir: true, fullPath: "folder" },
+    ];
+
+    const conflicts = await checkConflict(files, "/files/target/");
+
+    expect(conflicts).toHaveLength(0);
+  });
+
   it("returns no conflicts when the recursive listing fails", async () => {
     vi.mocked(api.fetchAll).mockRejectedValue(new Error("404"));
 
diff --git a/frontend/src/utils/upload.ts b/frontend/src/utils/upload.ts
index 994c95be..c4a9aab4 100644
--- a/frontend/src/utils/upload.ts
+++ b/frontend/src/utils/upload.ts
@@ -26,16 +26,24 @@ function conflictKey(item: UploadEntry): string {
  * server, so the caller can prompt the user to overwrite/rename/skip.
  *
  * The whole destination tree is fetched once and indexed by path relative to
- * the destination, then every file is looked up directly — no need to mirror
- * the upload's folder structure. Directories are never reported: an existing
- * folder is merged on upload, and a copy/move onto one is rejected server-side.
+ * the destination, then every entry is looked up directly — no need to mirror
+ * the upload's folder structure.
  *
- * @param files    - flat upload list to check
- * @param basePath - server destination path (e.g. "/files/uploads/")
+ * Directory handling differs by action, hence `includeDirectories`:
+ *  - Upload (false): an existing folder is silently merged, so only the
+ *    individual files inside it can conflict.
+ *  - Copy/move (true): the server stats the destination and rejects it whole if
+ *    a same-named entry exists, so the directory itself is a conflict. The list
+ *    only holds the top-level items being moved, so each is reported once.
+ *
+ * @param files              - flat upload list to check
+ * @param basePath           - server destination path (e.g. "/files/uploads/")
+ * @param includeDirectories - report directories as conflicts (copy/move)
  */
 export async function checkConflict(
   files: UploadList,
-  basePath: string
+  basePath: string,
+  includeDirectories = false
 ): Promise<ConflictingResource[]> {
   if (files.length === 0) return [];
 
@@ -62,7 +70,7 @@ export async function checkConflict(
 
   const conflicts: ConflictingResource[] = [];
   files.forEach((file, index) => {
-    if (file.isDir) return; // see directory note above
+    if (file.isDir && !includeDirectories) return; // see directory note above
 
     const server = serverMap.get(conflictKey(file));
     if (!server) return;
diff --git a/frontend/src/views/files/FileListing.vue b/frontend/src/views/files/FileListing.vue
index 06a010e4..9bf4c488 100644
--- a/frontend/src/views/files/FileListing.vue
+++ b/frontend/src/views/files/FileListing.vue
@@ -632,6 +632,7 @@ const copyCut = (event: Event | KeyboardEvent): void => {
       from: fileStore.req.items[i].url,
       name: fileStore.req.items[i].name,
       size: fileStore.req.items[i].size,
+      isDir: fileStore.req.items[i].isDir,
       modified: fileStore.req.items[i].modified,
     });
   }
@@ -661,6 +662,7 @@ const paste = async (event: Event) => {
       to,
       name: item.name,
       size: item.size,
+      isDir: item.isDir,
       modified: item.modified,
       overwrite: false,
       rename: clipboardStore.path == route.path,
@@ -697,7 +699,7 @@ const paste = async (event: Event) => {
   }
 
   const path = route.path.endsWith("/") ? route.path : route.path + "/";
-  const conflict = await upload.checkConflict(items, path);
+  const conflict = await upload.checkConflict(items, path, true);
 
   if (conflict.length > 0) {
     layoutStore.showHover({