diff --git a/CHANGELOG.md b/CHANGELOG.md
index 6fa25babc70..2e26fa9254b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## [Unreleased]
 
+### Fixed
+
+- **PR #2382** by @Michaelyklam (closes #2380) — `api/file/raw` now falls back to the requesting session's attachment inbox when a chat-upload filename is not present in the workspace. This keeps existing `api/file/raw?session_id=...&path=<filename>` image URLs working after uploads moved under `~/.hermes/webui/attachments/<session_id>/`, while preserving traversal protection and cross-session isolation.
+
 ## [v0.51.74] — 2026-05-16 — Release AX (stage-367 — 4-PR safe-lane batch — #2362 table-cell spacing + #2363 run-state-consistency RFC + #2365 custom_providers list-format + #2367 settings sidebar i18n)
 
 ### Added
diff --git a/api/routes.py b/api/routes.py
index 3ad444e92c7..d66970589a1 100644
--- a/api/routes.py
+++ b/api/routes.py
@@ -6360,10 +6360,34 @@ def _handle_media(handler, parsed):
             or html_inline_ok
         )
     ) else "attachment"
+    # _serve_file_bytes sends Content-Security-Policy when csp is set.
     csp = "sandbox allow-scripts" if html_inline_ok else None
     return _serve_file_bytes(handler, target, mime, disposition, "private, max-age=3600", csp=csp)
 
 
+def _file_raw_target(session, sid: str, rel: str) -> Path | None:
+    """Resolve /api/file/raw paths from the workspace or this session's uploads."""
+    try:
+        target = safe_resolve(Path(session.workspace), rel)
+    except ValueError:
+        target = None
+    if target and target.exists() and target.is_file():
+        return target
+
+    # Chat uploads now live in a per-session attachment inbox outside the
+    # workspace. Keep the public URL stable while scoping fallback lookup to
+    # the requesting session's own attachment directory.
+    try:
+        from api.upload import _session_attachment_dir
+
+        attachment_target = safe_resolve(_session_attachment_dir(sid), rel)
+    except Exception:
+        return None
+    if attachment_target.exists() and attachment_target.is_file():
+        return attachment_target
+    return None
+
+
 def _handle_file_raw(handler, parsed):
     qs = parse_qs(parsed.query)
     sid = qs.get("session_id", [""])[0]
@@ -6375,8 +6399,8 @@ def _handle_file_raw(handler, parsed):
         return bad(handler, "Session not found", 404)
     rel = qs.get("path", [""])[0]
     force_download = qs.get("download", [""])[0] == "1"
-    target = safe_resolve(Path(s.workspace), rel)
-    if not target.exists() or not target.is_file():
+    target = _file_raw_target(s, sid, rel)
+    if target is None:
         return j(handler, {"error": "not found"}, status=404)
     ext = target.suffix.lower()
     mime = MIME_MAP.get(ext, "application/octet-stream")
diff --git a/tests/test_sprint2.py b/tests/test_sprint2.py
index aa5c5f2aa9b..efb2085bbd7 100644
--- a/tests/test_sprint2.py
+++ b/tests/test_sprint2.py
@@ -67,7 +67,7 @@ def test_raw_endpoint_path_traversal_blocked(cleanup_test_sessions):
         get_raw(f"/api/file/raw?session_id={sid}&path=../../etc/passwd")
         assert False
     except urllib.error.HTTPError as e:
-        assert e.code in (400, 500)
+        assert e.code in (400, 404, 500)
 
 def test_raw_endpoint_missing_file_returns_404(cleanup_test_sessions):
     sid, _ = make_session_tracked(cleanup_test_sessions)
diff --git a/tests/test_sprint6.py b/tests/test_sprint6.py
index 6c2ba1df95c..fcfbbe1e7ff 100644
--- a/tests/test_sprint6.py
+++ b/tests/test_sprint6.py
@@ -1,5 +1,5 @@
 """Sprint 6 tests: Escape from editor, Phase D validation, HTML extraction, cron create, session export."""
-import json, uuid, pathlib, urllib.request, urllib.error
+import json, uuid, pathlib, urllib.parse, urllib.request, urllib.error
 REPO_ROOT = pathlib.Path(__file__).parent.parent.resolve()
 
 from tests._pytest_port import BASE
@@ -74,6 +74,37 @@ def test_file_raw_unknown_session():
     except urllib.error.HTTPError as e:
         assert e.code == 404
 
+def test_file_raw_serves_session_attachment_inbox(cleanup_test_sessions):
+    from api.upload import _session_attachment_dir
+
+    sid, workspace = make_session_tracked(cleanup_test_sessions)
+    filename = f"uploaded-chat-image-{uuid.uuid4().hex}.png"
+    attachment_dir = _session_attachment_dir(sid)
+    attachment_dir.mkdir(parents=True, exist_ok=True)
+    payload = b"fake-png-bytes"
+    (attachment_dir / filename).write_bytes(payload)
+
+    assert not (workspace / filename).exists(), "regression must exercise attachment fallback"
+    raw, headers, status = get_raw(
+        f"/api/file/raw?session_id={sid}&path={urllib.parse.quote(filename)}"
+    )
+    assert status == 200
+    assert raw == payload
+    assert "image/png" in headers.get("Content-Type", "")
+
+def test_file_raw_attachment_fallback_rejects_traversal(cleanup_test_sessions):
+    from api.upload import _session_attachment_dir
+
+    sid, _ = make_session_tracked(cleanup_test_sessions)
+    attachment_dir = _session_attachment_dir(sid)
+    attachment_dir.mkdir(parents=True, exist_ok=True)
+    (attachment_dir / "safe.txt").write_text("safe", encoding="utf-8")
+    try:
+        get_raw(f"/api/file/raw?session_id={sid}&path={urllib.parse.quote('../../safe.txt')}")
+        assert False, "Expected 404"
+    except urllib.error.HTTPError as e:
+        assert e.code == 404
+
 # ── Cron create ──
 
 def test_cron_create_requires_prompt():