diff --git a/tests/tools/test_credential_files.py b/tests/tools/test_credential_files.py
index 67fa8fd1b3..09b11d6ea1 100644
--- a/tests/tools/test_credential_files.py
+++ b/tests/tools/test_credential_files.py
@@ -362,6 +362,39 @@ class TestCacheDirectoryMounts:
 
         assert get_cache_directory_mounts() == []
 
+    def test_images_upload_dir_is_mounted(self, tmp_path, monkeypatch):
+        """The flat top-level ``images/`` upload dir is mounted (#69575).
+
+        Desktop / clipboard / PDF uploads land in ``HERMES_HOME/images``, not
+        under ``cache/``. Without this entry vision_analyze on a desktop upload
+        fails because the file is not reachable inside the sandbox.
+        """
+        hermes_home = tmp_path / ".hermes"
+        (hermes_home / "images").mkdir(parents=True)
+        monkeypatch.setenv("HERMES_HOME", str(hermes_home))
+
+        mounts = get_cache_directory_mounts()
+        by_container = {m["container_path"]: m["host_path"] for m in mounts}
+        assert "/root/.hermes/images" in by_container
+        assert by_container["/root/.hermes/images"] == str(hermes_home / "images")
+
+    def test_images_upload_file_maps_into_container(self, tmp_path, monkeypatch):
+        """A concrete upload under ``images/`` maps to its container path.
+
+        This is the reverse mapping vision uses to translate a container-visible
+        path back to the host mount; it must recognise the ``images/`` dir.
+        """
+        hermes_home = tmp_path / ".hermes"
+        (hermes_home / "images").mkdir(parents=True)
+        upload = hermes_home / "images" / "upload_20260722_181019_1.png"
+        upload.write_bytes(bytes.fromhex("89504e470d0a1a0a"))
+        monkeypatch.setenv("HERMES_HOME", str(hermes_home))
+
+        assert (
+            map_cache_path_to_container(str(upload))
+            == "/root/.hermes/images/upload_20260722_181019_1.png"
+        )
+
 
 class TestMapCachePathToContainer:
     """Tests for map_cache_path_to_container() — the backend-agnostic mapper."""
diff --git a/tests/tools/test_image_source.py b/tests/tools/test_image_source.py
index 8d4887629e..112dbc7037 100644
--- a/tests/tools/test_image_source.py
+++ b/tests/tools/test_image_source.py
@@ -106,6 +106,28 @@ class TestNonLocalBackendConfinement:
         assert res.data == PNG
         assert res.origin == "file"
 
+    @pytest.mark.asyncio
+    async def test_desktop_upload_images_dir_host_read(self, tmp_path, monkeypatch):
+        """Desktop/clipboard uploads under ``HERMES_HOME/images`` are host-read.
+
+        Regression for #69575: uploads land in the flat top-level ``images/``
+        dir (not ``cache/images``). Under a sandbox backend the vision resolver
+        must permit reading them host-side — otherwise it falls through to the
+        task-id-less sandbox reader and fails with "not reachable inside the
+        sandbox".
+        """
+        home = tmp_path / "hermes"
+        isrc = _reload(monkeypatch, home)
+        monkeypatch.setenv("TERMINAL_ENV", "docker")
+        upload = home / "images" / "upload_20260722_181019_1.png"
+        upload.parent.mkdir(parents=True)
+        upload.write_bytes(PNG)
+        # No sandbox env: an uploads path must be host-read directly, not routed
+        # to the in-sandbox exec-read.
+        res = await isrc.resolve_image_source(str(upload), isrc.ResolveContext())
+        assert res.data == PNG
+        assert res.origin == "file"
+
     @pytest.mark.asyncio
     async def test_host_secret_outside_cache_routes_to_sandbox_not_host(self, tmp_path, monkeypatch):
         """A non-cache host path (e.g. /etc/passwd) must NOT be host-read — it
diff --git a/tests/tui_gateway/test_session_images_dir.py b/tests/tui_gateway/test_session_images_dir.py
new file mode 100644
index 0000000000..0393ec80a2
--- /dev/null
+++ b/tests/tui_gateway/test_session_images_dir.py
@@ -0,0 +1,54 @@
+"""Write-side scoping for desktop/clipboard image uploads (#69575).
+
+Attach RPCs (``image.attach_bytes``, ``clipboard.paste``, ``pdf.attach``) run
+before ``prompt.submit`` installs the session's profile HERMES_HOME override, so
+the upload must be written under the session's *stored* ``profile_home`` — the
+same scope the Docker mount and the vision host-read allowlist resolve at run
+time. Otherwise, in a multi-profile / root-gateway deployment, the file is
+written to the launch home while the sandbox mounts (and vision reads) the
+profile home, and the agent can never see the upload it was handed.
+"""
+
+from pathlib import Path
+from unittest.mock import patch
+
+from tui_gateway.server import _session_images_dir
+
+
+def test_profile_home_session_writes_under_profile(tmp_path):
+    """A session pinned to a profile writes uploads under that profile's home."""
+    profile_home = tmp_path / ".hermes" / "profiles" / "coder"
+    session = {"profile_home": str(profile_home)}
+
+    assert _session_images_dir(session) == profile_home / "images"
+
+
+def test_launch_home_fallback_when_no_profile(tmp_path):
+    """No ``profile_home`` on the session → the gateway launch home is used."""
+    launch_home = tmp_path / ".hermes"
+    session = {}
+
+    with patch("tui_gateway.server._hermes_home", launch_home):
+        assert _session_images_dir(session) == launch_home / "images"
+
+
+def test_empty_profile_home_falls_back_to_launch_home(tmp_path):
+    """An empty-string ``profile_home`` is treated as absent, not as ``/images``."""
+    launch_home = tmp_path / ".hermes"
+    session = {"profile_home": ""}
+
+    with patch("tui_gateway.server._hermes_home", launch_home):
+        assert _session_images_dir(session) == launch_home / "images"
+
+
+def test_two_profiles_are_isolated(tmp_path):
+    """Uploads from different profile sessions never share an images dir."""
+    home_a = tmp_path / ".hermes" / "profiles" / "a"
+    home_b = tmp_path / ".hermes" / "profiles" / "b"
+
+    dir_a = _session_images_dir({"profile_home": str(home_a)})
+    dir_b = _session_images_dir({"profile_home": str(home_b)})
+
+    assert dir_a == home_a / "images"
+    assert dir_b == home_b / "images"
+    assert dir_a != dir_b
diff --git a/tools/credential_files.py b/tools/credential_files.py
index a86164ffc3..e57af0bbb4 100644
--- a/tools/credential_files.py
+++ b/tools/credential_files.py
@@ -395,6 +395,11 @@ _CACHE_DIRS: list[tuple[str, str]] = [
     ("cache/screenshots", "browser_screenshots"),
     ("cache/web", "web_cache"),
     ("cache/delegation", "delegation_cache"),
+    # Desktop/clipboard/PDF uploads land in the flat top-level ``images/`` dir
+    # (tui_gateway attach RPCs), not under ``cache/``. Mount it so vision can
+    # reach uploads inside sandbox containers (#69575). No legacy alias exists,
+    # so both tuple slots are ``images``.
+    ("images", "images"),
 ]
 
 
diff --git a/tools/image_source.py b/tools/image_source.py
index e46651e482..d41d3103e9 100644
--- a/tools/image_source.py
+++ b/tools/image_source.py
@@ -230,6 +230,7 @@ def _media_cache_roots() -> list:
     home = get_hermes_home()
     return [
         home / "cache",  # cache/images, cache/vision, cache/video(s), cache/audio
+        home / "images",  # desktop/clipboard/PDF uploads (tui_gateway) — #69575
         home / "image_cache",
         home / "audio_cache",
         home / "video_cache",
diff --git a/tui_gateway/methods_prompt.py b/tui_gateway/methods_prompt.py
index 763de70ac8..098b6aa4c2 100644
--- a/tui_gateway/methods_prompt.py
+++ b/tui_gateway/methods_prompt.py
@@ -301,7 +301,7 @@ def _(rid, params: dict) -> dict:
         return _err(rid, 5027, f"clipboard unavailable: {e}")
 
     session["image_counter"] = session.get("image_counter", 0) + 1
-    img_dir = _hermes_home / "images"
+    img_dir = _session_images_dir(session)
     img_dir.mkdir(parents=True, exist_ok=True)
     img_path = (
         img_dir
diff --git a/tui_gateway/server.py b/tui_gateway/server.py
index 2ecb4c3ed9..327ae0f717 100644
--- a/tui_gateway/server.py
+++ b/tui_gateway/server.py
@@ -9810,6 +9810,26 @@ def _allowed_image_extensions() -> frozenset[str]:
         return frozenset({".png", ".jpg", ".jpeg", ".gif", ".webp", ".bmp"})
 
 
+def _session_images_dir(session: dict) -> Path:
+    """Resolve the uploads ``images/`` dir against the session's effective home.
+
+    Attach RPCs (``image.attach_bytes``, ``clipboard.paste``, ``pdf.attach``)
+    run BEFORE ``prompt.submit`` installs the session's profile HERMES_HOME
+    override, so ``get_hermes_home()`` here would return the gateway's launch
+    home. In a multi-profile / root-gateway deployment that writes the upload to
+    the launch home's ``images/`` while the sandbox mount and the vision host-
+    read allowlist both resolve the *session profile's* ``images/`` at run time
+    — so the file the agent tries to read is never the file we wrote (#69575).
+
+    Anchor the write on the session's stored ``profile_home`` when present
+    (matching the mount/read scope), else fall back to the launch home. Keeps
+    per-profile isolation: a profile's uploads stay under that profile's home.
+    """
+    profile_home = session.get("profile_home")
+    base = Path(profile_home) if profile_home else _hermes_home
+    return base / "images"
+
+
 def _queue_attached_image(session: dict, img_bytes: bytes, ext: str, *, prefix: str) -> Path:
     """Write image bytes into the gateway's images dir and queue them.
 
@@ -9818,7 +9838,7 @@ def _queue_attached_image(session: dict, img_bytes: bytes, ext: str, *, prefix:
     the existing native-image-attach pipeline. Returns the written path.
     """
     session["image_counter"] = session.get("image_counter", 0) + 1
-    img_dir = _hermes_home / "images"
+    img_dir = _session_images_dir(session)
     img_dir.mkdir(parents=True, exist_ok=True)
     ts = datetime.now().strftime("%Y%m%d_%H%M%S")
     img_path = img_dir / f"{prefix}_{ts}_{session['image_counter']}{ext}"