diff --git a/.changeset/remove-broken-upload-file-button.md b/.changeset/remove-broken-upload-file-button.md
new file mode 100644
index 000000000..ef866f6ec
--- /dev/null
+++ b/.changeset/remove-broken-upload-file-button.md
@@ -0,0 +1,5 @@
+---
+"@inkeep/open-knowledge": patch
+---
+
+Remove the broken "Upload file" button from the file sidebar. This drops the upload-via-file-picker entry points: the sidebar toolbar button, the folder and empty-area right-click menu items, and the empty-state button. Drag-and-drop file upload onto the file tree is unchanged.
diff --git a/packages/app/src/components/FileSidebar.dom.test.tsx b/packages/app/src/components/FileSidebar.dom.test.tsx
index 4b4d4a117..f04384b28 100644
--- a/packages/app/src/components/FileSidebar.dom.test.tsx
+++ b/packages/app/src/components/FileSidebar.dom.test.tsx
@@ -92,7 +92,6 @@ const treeCalls = {
   expandAll: mock(() => {}),
   startCreating: mock((_kind: 'file' | 'folder', _parentDir: string) => {}),
   startCreatingFromTemplate: mock((_parentDir: string) => {}),
-  uploadFiles: mock((_parentDir: string) => {}),
 };
 const projectLocalPatch = mock((_patch: unknown) => projectPatchResult);
 const showItemInFolderMock = mock((_path: string) => Promise.resolve());
@@ -144,7 +143,6 @@ mock.module('@/components/FileTree', () => ({
           treeListeners.add(listener);
           return () => treeListeners.delete(listener);
         },
-        uploadFiles: treeCalls.uploadFiles,
       };
       ref?.(handle);
       return () => ref?.(null);
@@ -402,7 +400,6 @@ describe('FileSidebar runtime behavior', () => {
       treeCalls.expandAll,
       treeCalls.startCreating,
       treeCalls.startCreatingFromTemplate,
-      treeCalls.uploadFiles,
       projectLocalPatch,
       showItemInFolderMock,
       notifyViewMenuStateChangedMock,
@@ -489,11 +486,9 @@ describe('FileSidebar runtime behavior', () => {
     fireEvent.click(screen.getAllByRole('button', { name: 'New from template' })[0]);
     fireEvent.click(screen.getByRole('button', { name: 'Daily' }));
     fireEvent.click(screen.getAllByRole('button', { name: 'New folder' })[0]);
-    fireEvent.click(screen.getAllByRole('button', { name: 'Upload file' })[0]);
     expect(treeCalls.startCreating).toHaveBeenCalledWith('file', 'docs');
     expect(treeCalls.createFromTemplate).toHaveBeenCalledWith('docs', 'daily');
     expect(treeCalls.startCreating).toHaveBeenCalledWith('folder', 'docs');
-    expect(treeCalls.uploadFiles).toHaveBeenCalledWith('docs');
 
     expect(screen.getByRole('button', { name: 'Expand all' })).toBeTruthy();
     expect(screen.getByRole('button', { name: 'Collapse all' })).toBeTruthy();
@@ -520,7 +515,6 @@ describe('FileSidebar runtime behavior', () => {
       'empty-space-menu-new-file',
       'empty-space-menu-new-from-template',
       'empty-space-menu-new-folder',
-      'empty-space-menu-upload-file',
       'empty-space-menu-reveal-in-finder',
       'open-in-agent-empty-space-submenu',
       'empty-space-menu-copy-full-path',
@@ -539,11 +533,9 @@ describe('FileSidebar runtime behavior', () => {
     fireEvent.click(screen.getByTestId('empty-space-menu-new-from-template'));
     fireEvent.click(screen.getByRole('menuitem', { name: 'Root daily' }));
     fireEvent.click(screen.getByTestId('empty-space-menu-new-folder'));
-    fireEvent.click(screen.getByTestId('empty-space-menu-upload-file'));
     expect(treeCalls.startCreating).toHaveBeenCalledWith('file', '');
     expect(treeCalls.createFromTemplate).toHaveBeenCalledWith('', 'root-daily');
     expect(treeCalls.startCreating).toHaveBeenCalledWith('folder', '');
-    expect(treeCalls.uploadFiles).toHaveBeenCalledWith('');
 
     fireEvent.click(screen.getByTestId('empty-space-menu-reveal-in-finder'));
     expect(showItemInFolderMock).toHaveBeenCalledWith('/tmp/open-knowledge');
diff --git a/packages/app/src/components/FileSidebar.menu-action.dom.test.tsx b/packages/app/src/components/FileSidebar.menu-action.dom.test.tsx
index d81b1b4e0..7000a63fb 100644
--- a/packages/app/src/components/FileSidebar.menu-action.dom.test.tsx
+++ b/packages/app/src/components/FileSidebar.menu-action.dom.test.tsx
@@ -65,7 +65,6 @@ const treeCalls = {
   expandAll: mock(() => {}),
   startCreating: mock((_kind: 'file' | 'folder', _parentDir: string) => {}),
   startCreatingFromTemplate: mock((_parentDir: string) => {}),
-  uploadFiles: mock((_parentDir: string) => {}),
 };
 const projectLocalPatch = mock((_patch: unknown) => ({ ok: true as const }));
 let menuActionCallback: ((action: MenuAction) => void) | null = null;
@@ -85,7 +84,6 @@ mock.module('@/components/FileTree', () => ({
         startCreating: treeCalls.startCreating,
         startCreatingFromTemplate: treeCalls.startCreatingFromTemplate,
         subscribe: () => () => {},
-        uploadFiles: treeCalls.uploadFiles,
       };
       ref?.(handle);
       return () => ref?.(null);
@@ -232,7 +230,6 @@ describe('FileSidebar menu-action runtime routing', () => {
       treeCalls.expandAll,
       treeCalls.startCreating,
       treeCalls.startCreatingFromTemplate,
-      treeCalls.uploadFiles,
     ]) {
       fn.mockClear();
     }
diff --git a/packages/app/src/components/FileSidebar.tsx b/packages/app/src/components/FileSidebar.tsx
index 777cfd66e..3d55be52d 100644
--- a/packages/app/src/components/FileSidebar.tsx
+++ b/packages/app/src/components/FileSidebar.tsx
@@ -9,7 +9,6 @@ import {
   ListCollapse,
   SquarePen,
   UnfoldVertical,
-  Upload,
 } from 'lucide-react';
 import { type ComponentProps, type FC, type MouseEventHandler, useEffect, useState } from 'react';
 import { ErrorBoundary } from 'react-error-boundary';
@@ -208,10 +207,6 @@ function FileSidebarInner({ onOpenSearch }: FileSidebarProps) {
     if (!workspace) return;
     tree?.startCreating('folder', '');
   };
-  const handleEmptySpaceUploadFile = () => {
-    if (!workspace) return;
-    tree?.uploadFiles('');
-  };
   const handleEmptySpaceReveal = () => {
     if (!workspace || !bridge) return;
     void bridge.shell.showItemInFolder(workspace.contentDir);
@@ -544,11 +539,6 @@ function FileSidebarInner({ onOpenSearch }: FileSidebarProps) {
                   label={t`New folder`}
                   onClick={() => tree?.startCreating('folder', initialCreateDir)}
                 />
-                <ToolbarButton
-                  icon={Upload}
-                  label={t`Upload file`}
-                  onClick={() => tree?.uploadFiles(initialCreateDir)}
-                />
               </div>
             </SidebarHeader>
             {/*
@@ -662,12 +652,12 @@ function FileSidebarInner({ onOpenSearch }: FileSidebarProps) {
         </ContextMenuTrigger>
         <ContextMenuContent>
           {/*
-           * Empty-space menu — 12 items, 4 sections.
+           * Empty-space menu — 11 items, 4 sections.
            *
-           * Section 1: Creation and upload (always visible). New file / from
+           * Section 1: Creation (always visible). New file / from
            * template / folder dispatch the project-root creation flow
-           * (parentDir = '' → contentDir). Upload opens the project-root file
-           * picker. Disabled when workspace hasn't resolved.
+           * (parentDir = '' → contentDir). Disabled when workspace hasn't
+           * resolved.
            *
            * Section 2: Act-on-project. Reveal in Finder
            * is Electron-only (`if (!bridge) return null`); Open with AI submenu
@@ -719,14 +709,6 @@ function FileSidebarInner({ onOpenSearch }: FileSidebarProps) {
             <FolderPlus aria-hidden="true" />
             <Trans>New folder</Trans>
           </ContextMenuItem>
-          <ContextMenuItem
-            disabled={!workspace}
-            onSelect={handleEmptySpaceUploadFile}
-            data-testid="empty-space-menu-upload-file"
-          >
-            <Upload aria-hidden="true" />
-            <Trans>Upload file</Trans>
-          </ContextMenuItem>
           <ContextMenuSeparator />
           {bridge ? (
             <ContextMenuItem
diff --git a/packages/app/src/components/FileTree.tsx b/packages/app/src/components/FileTree.tsx
index 8889a88af..9582adf65 100644
--- a/packages/app/src/components/FileTree.tsx
+++ b/packages/app/src/components/FileTree.tsx
@@ -42,7 +42,6 @@ import {
   Trash2,
   TriangleAlert,
   UnfoldVertical,
-  Upload,
 } from 'lucide-react';
 import { __iconNode as botIcon } from 'lucide-react/dist/esm/icons/bot';
 import { __iconNode as link2Icon } from 'lucide-react/dist/esm/icons/link-2';
@@ -483,7 +482,6 @@ interface FileTreeMenuProps {
    *  (`appearance.sidebar.{showHiddenFiles,showAllFiles}`). */
   mergedConfig: Config | null;
   onStartCreating: (kind: 'file' | 'folder', parentDir: string) => void;
-  onUploadFiles: (parentDir: string) => void;
   /** Inline create-from-template for the given parent dir + template name —
    *  same inline-rename fast path as `onStartCreating`, seeded from a template.
    *  Drives the folder menu's "New from template" hover submenu. */
@@ -544,35 +542,6 @@ function isEditableKeyboardTarget(target: EventTarget | null): boolean {
   );
 }
 
-function chooseSidebarUploadFiles(): Promise<readonly File[]> {
-  if (typeof document === 'undefined') return Promise.resolve([]);
-
-  return new Promise((resolve) => {
-    const input = document.createElement('input');
-    input.type = 'file';
-    input.multiple = true;
-    input.tabIndex = -1;
-    input.style.position = 'fixed';
-    input.style.inlineSize = '1px';
-    input.style.blockSize = '1px';
-    input.style.opacity = '0';
-    input.style.pointerEvents = 'none';
-
-    let settled = false;
-    const settle = (files: readonly File[]) => {
-      if (settled) return;
-      settled = true;
-      input.remove();
-      resolve(files);
-    };
-
-    input.addEventListener('change', () => settle(Array.from(input.files ?? [])), { once: true });
-    input.addEventListener('cancel', () => settle([]), { once: true });
-    document.body.append(input);
-    input.click();
-  });
-}
-
 function collectTabsToCloseForDelete(
   targets: readonly FileTreeTarget[],
   documents: readonly FileEntry[],
@@ -630,7 +599,6 @@ function FileTreeMenu({
   projectLocalBinding,
   mergedConfig,
   onStartCreating,
-  onUploadFiles,
   onCreateFromTemplate,
   onDuplicate,
   onDelete,
@@ -778,16 +746,6 @@ function FileTreeMenu({
               <FolderPlus aria-hidden="true" />
               <Trans>New folder</Trans>
             </DropdownMenuItem>
-            <DropdownMenuItem
-              disabled={anyActionBusy}
-              onSelect={() => {
-                closeForInlineSurface();
-                onUploadFiles(treeDirectoryPathToFolderPath(item.path));
-              }}
-            >
-              <Upload aria-hidden="true" />
-              <Trans>Upload file</Trans>
-            </DropdownMenuItem>
             <DropdownMenuSeparator />
             <RevealInFileManagerMenuItem item={item} workspace={workspace} onClose={close} />
             <OpenInAgentContextSubmenu
@@ -1044,7 +1002,6 @@ function FileTreeMenu({
 
 export interface FileTreeHandle {
   startCreating(kind: 'file' | 'folder', parentDir: string): void;
-  uploadFiles(parentDir: string): void;
   /** Open NewItemDialog at the given parentDir so the template picker is
    *  reachable. Used by the native macOS File menu's "New from Template…"
    *  item, where an inline hover-submenu of templates isn't expressible. */
@@ -2404,17 +2361,6 @@ export function FileTree({ ref }: { ref?: Ref<FileTreeHandle | null> }) {
     }
   }
 
-  async function uploadFilesToTargetFromPicker(parentDir: string) {
-    if (busyPathRef.current !== null) return;
-    const files = await chooseSidebarUploadFiles();
-    if (files.length === 0) return;
-    const uploadBusyPath =
-      parentDir === ''
-        ? FILE_TREE_EXTERNAL_FILE_DROP_BUSY_PATH
-        : folderPathToTreeDirectoryPath(parentDir);
-    await uploadExternalFilesToTarget(files, parentDir, uploadBusyPath);
-  }
-
   function startCreatingFromTemplate(parentDir: string) {
     setNewItemRequest({ parentDir });
   }
@@ -2756,11 +2702,9 @@ export function FileTree({ ref }: { ref?: Ref<FileTreeHandle | null> }) {
 
   const startCreatingRef = useRef(startCreating);
   const startCreatingFromTemplateRef = useRef(startCreatingFromTemplate);
-  const uploadFilesRef = useRef(uploadFilesToTargetFromPicker);
   useEffect(() => {
     startCreatingRef.current = startCreating;
     startCreatingFromTemplateRef.current = startCreatingFromTemplate;
-    uploadFilesRef.current = uploadFilesToTargetFromPicker;
   });
 
   useImperativeHandle(
@@ -2769,9 +2713,6 @@ export function FileTree({ ref }: { ref?: Ref<FileTreeHandle | null> }) {
       startCreating(kind, parentDir) {
         void startCreatingRef.current(kind, parentDir);
       },
-      uploadFiles(parentDir) {
-        void uploadFilesRef.current(parentDir);
-      },
       startCreatingFromTemplate(parentDir) {
         startCreatingFromTemplateRef.current(parentDir);
       },
@@ -3337,17 +3278,6 @@ export function FileTree({ ref }: { ref?: Ref<FileTreeHandle | null> }) {
         >
           <Trans>Create your first file</Trans>
         </Button>
-        <Button
-          variant="link"
-          size="sm"
-          className="font-mono uppercase"
-          onClick={() => {
-            void uploadFilesToTargetFromPicker('');
-          }}
-        >
-          <Upload aria-hidden="true" />
-          <Trans>Upload file</Trans>
-        </Button>
       </section>
     );
   }
@@ -3394,9 +3324,6 @@ export function FileTree({ ref }: { ref?: Ref<FileTreeHandle | null> }) {
               projectLocalBinding={projectLocalBinding}
               mergedConfig={merged}
               onStartCreating={startCreating}
-              onUploadFiles={(parentDir) => {
-                void uploadFilesToTargetFromPicker(parentDir);
-              }}
               onCreateFromTemplate={(parentDir, templateName) =>
                 startCreating('file', parentDir, { template: templateName })
               }
diff --git a/packages/app/src/locales/en/messages.po b/packages/app/src/locales/en/messages.po
index 44bad04b5..9c0374aa6 100644
--- a/packages/app/src/locales/en/messages.po
+++ b/packages/app/src/locales/en/messages.po
@@ -5961,8 +5961,6 @@ msgstr "Upload failed — please try again"
 msgid "Upload failed: {message}"
 msgstr "Upload failed: {message}"
 
-#: src/components/FileSidebar.tsx
-#: src/components/FileTree.tsx
 #: src/editor/components/PropPanel.tsx
 msgid "Upload file"
 msgstr "Upload file"
diff --git a/packages/app/src/locales/pseudo/messages.po b/packages/app/src/locales/pseudo/messages.po
index e3ead4719..43bd4d807 100644
--- a/packages/app/src/locales/pseudo/messages.po
+++ b/packages/app/src/locales/pseudo/messages.po
@@ -5956,8 +5956,6 @@ msgstr ""
 msgid "Upload failed: {message}"
 msgstr ""
 
-#: src/components/FileSidebar.tsx
-#: src/components/FileTree.tsx
 #: src/editor/components/PropPanel.tsx
 msgid "Upload file"
 msgstr ""