diff --git a/README.md b/README.md
index e218cc26..9455ed0b 100644
--- a/README.md
+++ b/README.md
@@ -331,6 +331,11 @@ services:
       - termix-data:/app/data
     environment:
       PORT: "8080"
+      GUACD_HOST: "guacd"
+      GUACD_TUNNEL_HOST: "termix"
+      GUACD_RECORDING_PATH: "/termix-data/session_recordings/guacamole"
+      # guacd, not the Termix container, reads and writes redirected-drive files.
+      GUACD_DRIVE_PATH: "/termix-data/rdp-drive"
     depends_on:
       - guacd
     networks:
@@ -340,8 +345,10 @@ services:
     image: guacamole/guacd:1.6.0
     container_name: guacd
     restart: unless-stopped
-    ports:
-      - "4822:4822"
+    volumes:
+      # The official guacd image runs as a non-root user. Keep the drive path
+      # in this writable shared volume instead of bind-mounting /drive.
+      - termix-data:/termix-data
     networks:
       - termix-net
 
diff --git a/src/ui/features/guacamole/GuacamoleApp.tsx b/src/ui/features/guacamole/GuacamoleApp.tsx
index eb6f2758..f8310d8b 100644
--- a/src/ui/features/guacamole/GuacamoleApp.tsx
+++ b/src/ui/features/guacamole/GuacamoleApp.tsx
@@ -26,6 +26,8 @@ import { resolveConnectionOrigin } from "@/lib/connection-origin.ts";
 import { useTranslation } from "react-i18next";
 import { GuacamoleToolbar } from "@/features/guacamole/GuacamoleToolbar.tsx";
 import { GuacamoleFileBrowser } from "@/features/guacamole/GuacamoleFileBrowser.tsx";
+import { describeUploadError } from "@/features/guacamole/guacamole-filesystem.ts";
+import { canUploadToRdpDrive } from "@/features/guacamole/guacamole-file-drop.ts";
 import { Button } from "@/components/button.tsx";
 import { Input } from "@/components/input.tsx";
 import { PasswordInput } from "@/components/password-input.tsx";
@@ -212,12 +214,36 @@ const GuacamoleAppInner = React.forwardRef<
   const allowUpload = guacConfig.disableUpload !== true;
   const allowDownload = guacConfig.disableDownload !== true;
 
-  // A dropped file has nowhere to go until the browser is showing the target
-  // directory, so opening it is part of accepting the drop.
-  const handleDropFiles = useCallback((files: File[]) => {
-    setPendingUploads(files);
-    setFileBrowserOpen(true);
-  }, []);
+  // Prefer the browsable filesystem's current directory. guacd may expose the
+  // RDP drive only through the connection-level file stream, in which case the
+  // standard direct upload still lands in the redirected drive.
+  const handleDropFiles = useCallback(
+    (files: File[]) => {
+      if (filesystem) {
+        setPendingUploads(files);
+        setFileBrowserOpen(true);
+        return;
+      }
+
+      void (async () => {
+        for (const file of files) {
+          try {
+            const display = displayRef.current;
+            if (!display) throw new Error("RDP session is not ready");
+            await display.uploadFile(file);
+            toast.success(t("guacamole.files.uploaded", { name: file.name }));
+          } catch (error) {
+            toast.error(
+              describeUploadError(error, (key) =>
+                t(`guacamole.files.${key}`, { name: file.name }),
+              ),
+            );
+          }
+        }
+      })();
+    },
+    [filesystem, t],
+  );
 
   const handleDropUnavailable = useCallback(() => {
     toast.error(
@@ -526,7 +552,11 @@ const GuacamoleAppInner = React.forwardRef<
         }}
         isVisible={isVisible}
         touchMode={touchMode}
-        allowUpload={allowUpload && filesystem !== null}
+        allowUpload={canUploadToRdpDrive(
+          allowUpload,
+          guacConfig.enableDrive === true,
+          filesystem !== null,
+        )}
         onConnect={() => setIsDisplayReady(true)}
         onError={(err) => {
           setConnectionError(err);
diff --git a/src/ui/features/guacamole/GuacamoleDisplay.tsx b/src/ui/features/guacamole/GuacamoleDisplay.tsx
index 14fab6a9..5f6605ab 100644
--- a/src/ui/features/guacamole/GuacamoleDisplay.tsx
+++ b/src/ui/features/guacamole/GuacamoleDisplay.tsx
@@ -25,6 +25,10 @@ import {
   getFileDropDisposition,
   hasDraggedFiles,
 } from "./guacamole-file-drop.ts";
+import {
+  uploadFileToClient,
+  type GuacamoleFileStreamClient,
+} from "./guacamole-filesystem.ts";
 import { guacStateToStage } from "@/components/connection/connection-status.ts";
 import type { ConnectionStage } from "@/types/connection-log.ts";
 import { clampGuacamoleZoom, stepGuacamoleZoom } from "./guacamole-zoom.ts";
@@ -53,6 +57,7 @@ export interface GuacamoleDisplayHandle {
   sendMouse: (x: number, y: number, buttonMask: number) => void;
   setClipboard: (data: string) => void;
   getFilesystem: () => Guacamole.Object | null;
+  uploadFile: (file: File) => Promise<void>;
   zoomIn: () => number;
   zoomOut: () => number;
   resetZoom: () => number;
@@ -193,6 +198,14 @@ export const GuacamoleDisplay = forwardRef<
       }
     },
     getFilesystem: () => filesystemRef.current,
+    uploadFile: (file: File) => {
+      const client = clientRef.current;
+      if (!client) return Promise.reject(new Error("RDP session is not ready"));
+      return uploadFileToClient(
+        client as unknown as GuacamoleFileStreamClient,
+        file,
+      );
+    },
     zoomIn: () => applyZoom(stepGuacamoleZoom(zoomRef.current, 1)),
     zoomOut: () => applyZoom(stepGuacamoleZoom(zoomRef.current, -1)),
     resetZoom: () => applyZoom(1),
diff --git a/src/ui/features/guacamole/guacamole-file-drop.ts b/src/ui/features/guacamole/guacamole-file-drop.ts
index 07b0c8ee..b1fe2273 100644
--- a/src/ui/features/guacamole/guacamole-file-drop.ts
+++ b/src/ui/features/guacamole/guacamole-file-drop.ts
@@ -12,3 +12,11 @@ export function getFileDropDisposition(
   if (!hasDraggedFiles(types) || fileCount === 0) return "ignore";
   return canUpload ? "upload" : "reject";
 }
+
+export function canUploadToRdpDrive(
+  uploadAllowed: boolean,
+  driveEnabled: boolean,
+  hasFilesystem: boolean,
+): boolean {
+  return uploadAllowed && (driveEnabled || hasFilesystem);
+}
diff --git a/src/ui/features/guacamole/guacamole-filesystem.ts b/src/ui/features/guacamole/guacamole-filesystem.ts
index 5504c047..a0ae0a1c 100644
--- a/src/ui/features/guacamole/guacamole-filesystem.ts
+++ b/src/ui/features/guacamole/guacamole-filesystem.ts
@@ -1,5 +1,11 @@
 import Guacamole from "guacamole-common-js";
 
+// The bundled Guacamole runtime exposes Client.createFileStream(), but the
+// package's older TypeScript declaration omits it.
+export interface GuacamoleFileStreamClient {
+  createFileStream(mimetype: string, filename: string): Guacamole.OutputStream;
+}
+
 // The root stream of a Guacamole.Object maps stream name to mimetype; a stream
 // carrying that same mimetype is itself a directory.
 export const STREAM_INDEX_MIMETYPE =
@@ -123,12 +129,45 @@ export function uploadFile(
   file: File,
   onProgress?: (sent: number, total: number) => void,
 ): Promise<void> {
-  return new Promise((resolve, reject) => {
-    const path = joinPath(directory, file.name);
-    const stream = filesystem.createOutputStream(
+  return writeUpload(
+    filesystem.createOutputStream(
       file.type || "application/octet-stream",
-      path,
-    );
+      joinPath(directory, file.name),
+    ),
+    file,
+    onProgress,
+  );
+}
+
+/**
+ * Uploads through Guacamole's connection-level file stream. RDP exposes this
+ * path even when guacd does not advertise a browsable filesystem object, so
+ * display drops must not depend on `Client.onfilesystem` having fired.
+ */
+export function uploadFileToClient(
+  client: GuacamoleFileStreamClient,
+  file: File,
+  onProgress?: (sent: number, total: number) => void,
+): Promise<void> {
+  return writeUpload(createClientFileStream(client, file), file, onProgress);
+}
+
+export function createClientFileStream(
+  client: GuacamoleFileStreamClient,
+  file: File,
+): Guacamole.OutputStream {
+  return client.createFileStream(
+    file.type || "application/octet-stream",
+    file.name,
+  );
+}
+
+function writeUpload(
+  stream: Guacamole.OutputStream,
+  file: File,
+  onProgress?: (sent: number, total: number) => void,
+): Promise<void> {
+  return new Promise((resolve, reject) => {
     const writer = new Guacamole.BlobWriter(stream);
 
     // A rejected blob stops the writer without firing onerror or oncomplete —
diff --git a/src/ui/tests/features/guacamole/GuacamoleToolbar.test.tsx b/src/ui/tests/features/guacamole/GuacamoleToolbar.test.tsx
index 7760e897..c58dc1f9 100644
--- a/src/ui/tests/features/guacamole/GuacamoleToolbar.test.tsx
+++ b/src/ui/tests/features/guacamole/GuacamoleToolbar.test.tsx
@@ -19,6 +19,7 @@ describe("GuacamoleToolbar Windows key", () => {
         sendMouse: vi.fn(),
         setClipboard: vi.fn(),
         getFilesystem: () => null,
+        uploadFile: async () => {},
         zoomIn: vi.fn(() => 1.25),
         zoomOut: vi.fn(() => 0.75),
         resetZoom: vi.fn(() => 1),
@@ -60,6 +61,7 @@ describe("GuacamoleToolbar Windows key", () => {
         sendMouse: vi.fn(),
         setClipboard: vi.fn(),
         getFilesystem: () => null,
+        uploadFile: async () => {},
         zoomIn,
         zoomOut,
         resetZoom,
diff --git a/src/ui/tests/features/guacamole/guacamole-file-drop.test.ts b/src/ui/tests/features/guacamole/guacamole-file-drop.test.ts
index dd2968dd..e7728c99 100644
--- a/src/ui/tests/features/guacamole/guacamole-file-drop.test.ts
+++ b/src/ui/tests/features/guacamole/guacamole-file-drop.test.ts
@@ -1,5 +1,6 @@
 import { describe, expect, it } from "vitest";
 import {
+  canUploadToRdpDrive,
   getFileDropDisposition,
   hasDraggedFiles,
 } from "@/features/guacamole/guacamole-file-drop.ts";
@@ -14,4 +15,11 @@ describe("Guacamole file drop", () => {
     expect(getFileDropDisposition(["Files"], 1, false)).toBe("reject");
     expect(getFileDropDisposition(["Files"], 1, true)).toBe("upload");
   });
+
+  it("accepts an enabled RDP drive before a filesystem object is advertised", () => {
+    expect(canUploadToRdpDrive(true, true, false)).toBe(true);
+    expect(canUploadToRdpDrive(true, false, true)).toBe(true);
+    expect(canUploadToRdpDrive(true, false, false)).toBe(false);
+    expect(canUploadToRdpDrive(false, true, true)).toBe(false);
+  });
 });
diff --git a/src/ui/tests/features/guacamole/guacamole-filesystem.test.ts b/src/ui/tests/features/guacamole/guacamole-filesystem.test.ts
index 3fe20f89..1abc5bf5 100644
--- a/src/ui/tests/features/guacamole/guacamole-filesystem.test.ts
+++ b/src/ui/tests/features/guacamole/guacamole-filesystem.test.ts
@@ -1,4 +1,4 @@
-import { describe, expect, it } from "vitest";
+import { describe, expect, it, vi } from "vitest";
 import {
   STREAM_INDEX_MIMETYPE,
   basename,
@@ -6,7 +6,10 @@ import {
   joinPath,
   parentPath,
   parseDirectoryIndex,
+  createClientFileStream,
+  type GuacamoleFileStreamClient,
 } from "../../../features/guacamole/guacamole-filesystem.js";
+import type Guacamole from "guacamole-common-js";
 
 describe("path helpers", () => {
   it("joins onto the root without doubling the separator", () => {
@@ -86,3 +89,19 @@ describe("parseDirectoryIndex", () => {
     expect(parseDirectoryIndex("{}", "/")).toEqual([]);
   });
 });
+
+describe("direct RDP upload", () => {
+  it("opens a connection-level file stream when no filesystem object is available", () => {
+    const stream = {} as Guacamole.OutputStream;
+    const client = {
+      createFileStream: vi.fn(() => stream),
+    } as GuacamoleFileStreamClient;
+    const file = new File(["hello"], "notes.txt", { type: "text/plain" });
+
+    expect(createClientFileStream(client, file)).toBe(stream);
+    expect(client.createFileStream).toHaveBeenCalledWith(
+      "text/plain",
+      "notes.txt",
+    );
+  });
+});