diff --git a/routes/upload_routes.py b/routes/upload_routes.py
index 265e708fc..92bbb84ea 100644
--- a/routes/upload_routes.py
+++ b/routes/upload_routes.py
@@ -25,7 +25,7 @@ from src.auth_helpers import effective_user, is_delegated_credential
 from src.owner_identity import auth_disabled, is_request_sentinel_owner
 from src.attachment_refs import attachment_refs_from_metadata
 from src.constants import GENERATED_IMAGES_DIR
-from src.path_confinement import is_inside
+from src.path_confinement import PathEscape, canonical_root, confine, is_inside
 from src.upload_handler import (
     UploadCleanupSafetyError,
     count_recent_uploads,
@@ -154,31 +154,47 @@ def setup_upload_routes(upload_handler):
 
     def _upload_root() -> str:
         from src.constants import UPLOAD_DIR
-        return os.path.realpath(getattr(upload_handler, "upload_dir", UPLOAD_DIR))
+        return canonical_root(getattr(upload_handler, "upload_dir", UPLOAD_DIR))
 
     def _path_inside_upload_dir(path: str) -> bool:
         return is_inside(_upload_root(), path)
 
     def _resolve_upload_path(file_id: str) -> str:
-        from src.constants import UPLOAD_DIR
-        upload_root = os.path.normpath(getattr(upload_handler, "upload_dir", UPLOAD_DIR))
         safe_id = secure_filename(os.path.basename(file_id))
-        direct = os.path.normpath(os.path.join(upload_root, safe_id))
-        if not direct.startswith(upload_root + os.sep) or not _path_inside_upload_dir(direct):
-            raise HTTPException(403, "Access denied")
+        if not safe_id:
+            raise HTTPException(400, "Invalid file ID")
+        root = _upload_root()
+
+        direct = os.path.normpath(os.path.join(root, safe_id))
         if os.path.lexists(direct):
-            if os.path.isfile(direct):
-                return direct
+            try:
+                canonical_direct = confine(root, direct, allow_root=False)
+            except (PathEscape, ValueError):
+                raise HTTPException(403, "Access denied")
+            if os.path.isfile(canonical_direct):
+                return canonical_direct
             raise HTTPException(404, "File not found")
 
-        for root, _dirs, files in os.walk(upload_root, followlinks=False):
+        info = _load_upload_info(safe_id)
+        stored_path = (info or {}).get("path")
+        if stored_path:
+            try:
+                canonical_stored = confine(root, stored_path, allow_root=False)
+                if os.path.isfile(canonical_stored):
+                    return canonical_stored
+            except (PathEscape, ValueError):
+                raise HTTPException(403, "Access denied")
+
+        for walk_root, _dirs, files in os.walk(root, followlinks=False):
             if safe_id not in files:
                 continue
-            path = os.path.normpath(os.path.join(root, safe_id))
-            if not path.startswith(upload_root + os.sep) or not _path_inside_upload_dir(path):
+            cand = os.path.normpath(os.path.join(walk_root, safe_id))
+            try:
+                canonical_cand = confine(root, cand, allow_root=False)
+            except (PathEscape, ValueError):
                 raise HTTPException(403, "Access denied")
-            if os.path.isfile(path):
-                return path
+            if os.path.isfile(canonical_cand):
+                return canonical_cand
             raise HTTPException(404, "File not found")
 
         raise HTTPException(404, "File not found")
@@ -457,8 +473,12 @@ def setup_upload_routes(upload_handler):
             original_name = info.get("name", safe_file_id)
         file_owner = info.get("owner") if info else None
         _verify_upload_access(request, file_owner)
-        upload_root = os.path.normpath(_upload_root())
-        path = os.path.normpath(_resolve_upload_path(safe_file_id))
+        upload_root = _upload_root()
+        path = _resolve_upload_path(safe_file_id)
+        try:
+            path = confine(upload_root, path, allow_root=False)
+        except (PathEscape, ValueError):
+            raise HTTPException(403, "Access denied")
         if not path.startswith(upload_root + os.sep) or not _path_inside_upload_dir(path):
             raise HTTPException(403, "Access denied")
         mime = (info or {}).get("mime") or _mt.guess_type(path)[0] or "application/octet-stream"
@@ -468,6 +488,10 @@ def setup_upload_routes(upload_handler):
         if thumb and mime.startswith("image/"):
             thumb_dir = os.path.normpath(os.path.join(upload_root, ".thumbs"))
             thumb_path = os.path.normpath(os.path.join(thumb_dir, safe_file_id + ".jpg"))
+            try:
+                thumb_path = confine(upload_root, thumb_path, allow_root=False)
+            except (PathEscape, ValueError):
+                raise HTTPException(403, "Access denied")
             if not thumb_path.startswith(thumb_dir + os.sep) or not _path_inside_upload_dir(thumb_path):
                 raise HTTPException(403, "Access denied")
             if request.method == "HEAD":
@@ -517,9 +541,10 @@ def setup_upload_routes(upload_handler):
         return next((fi for fi in db.values() if fi.get("id") == file_id), None)
 
     def _vision_cache_path(file_id: str) -> str:
-        cache_dir = os.path.join(_upload_root(), ".vision")
+        safe_id = secure_filename(os.path.basename(file_id))
+        cache_dir = os.path.normpath(os.path.join(_upload_root(), ".vision"))
         os.makedirs(cache_dir, exist_ok=True)
-        return os.path.join(cache_dir, file_id + ".txt")
+        return os.path.normpath(os.path.join(cache_dir, safe_id + ".txt"))
 
     def _sync_gallery_caption_for_upload(info: dict | None, owner: str | None, text: str) -> None:
         """Copy upload OCR/vision text onto the promoted gallery image row."""
diff --git a/tests/test_upload_confinement_compatibility.py b/tests/test_upload_confinement_compatibility.py
new file mode 100644
index 000000000..aa39220da
--- /dev/null
+++ b/tests/test_upload_confinement_compatibility.py
@@ -0,0 +1,415 @@
+"""Regression suite for upload confinement compatibility on symlinked and ordinary roots.
+
+Verifies:
+1. Ordinary upload root.
+2. Upload root that is a symlink to an authorized directory.
+3. Valid file in nested upload directory.
+4. Symlinked in-root directory resolving safely inside the root.
+5. Symlink escaping outside the authorized root — rejected.
+6. Malformed upload ID — rejected.
+7. Missing upload — rejected.
+8. Foreign-user upload — rejected.
+9. Valid GET/HEAD parity on both ordinary and symlinked roots.
+10. Cached, missing and stale thumbnail HEAD behavior (zero body, no generation).
+11. No directory traversal or unauthorized file disclosure.
+"""
+from __future__ import annotations
+
+import json
+import os
+import time
+from pathlib import Path
+from types import SimpleNamespace
+
+import pytest
+from fastapi import APIRouter, FastAPI
+from starlette.testclient import TestClient
+
+from src.path_confinement import canonical_root, confine, PathEscape
+from src.upload_handler import UploadHandler, secure_filename
+import routes.upload_routes as upload_routes_mod
+import src.constants as constants
+
+
+class _AuthManager:
+    is_configured = True
+
+    def __init__(self, admins=("admin",)):
+        self._admins = set(admins)
+
+    def is_admin(self, user: str | None) -> bool:
+        return user in self._admins
+
+
+def _build_test_app(handler: UploadHandler, default_user: str | None = "alice") -> FastAPI:
+    test_router = APIRouter(prefix="/api/upload", tags=["uploads"])
+    orig_router = upload_routes_mod.router
+    upload_routes_mod.router = test_router
+    try:
+        upload_routes_mod.setup_upload_routes(handler)
+    finally:
+        upload_routes_mod.router = orig_router
+
+    app = FastAPI()
+    app.state.auth_manager = _AuthManager()
+
+    @app.middleware("http")
+    async def inject_user(request, call_next):
+        header_user = request.headers.get("x-test-user")
+        if header_user is not None:
+            request.state.current_user = header_user if header_user != "none" else None
+        else:
+            request.state.current_user = default_user
+        return await call_next(request)
+
+    app.include_router(test_router)
+    return app
+
+
+def _create_fixture_env(tmp_path: Path, monkeypatch, *, symlinked_root: bool = False):
+    if symlinked_root:
+        real_uploads = tmp_path / "real_uploads"
+        real_uploads.mkdir(parents=True, exist_ok=True)
+        upload_dir = tmp_path / "symlink_uploads"
+        os.symlink(real_uploads, upload_dir)
+        storage_base = real_uploads
+    else:
+        upload_dir = tmp_path / "ordinary_uploads"
+        upload_dir.mkdir(parents=True, exist_ok=True)
+        storage_base = upload_dir
+
+    dated_dir = storage_base / "2026" / "10" / "29"
+    dated_dir.mkdir(parents=True, exist_ok=True)
+
+    alice_id = "a" * 32 + ".png"
+    bob_id = "b" * 32 + ".png"
+    nested_id = "c" * 32 + ".png"
+
+    # Valid PNG image bytes using PIL
+    from PIL import Image
+    import io
+    buf = io.BytesIO()
+    Image.new("RGB", (10, 10), "red").save(buf, format="PNG")
+    png_bytes = buf.getvalue()
+
+    alice_path = storage_base / alice_id
+    bob_path = storage_base / bob_id
+    nested_path = dated_dir / nested_id
+
+    alice_path.write_bytes(png_bytes)
+    bob_path.write_bytes(png_bytes)
+    nested_path.write_bytes(png_bytes)
+
+    index = {
+        f"alice:{alice_id}": {
+            "id": alice_id,
+            "path": str(alice_path),
+            "mime": "image/png",
+            "size": len(png_bytes),
+            "name": "alice.png",
+            "original_name": "alice.png",
+            "owner": "alice",
+        },
+        f"bob:{bob_id}": {
+            "id": bob_id,
+            "path": str(bob_path),
+            "mime": "image/png",
+            "size": len(png_bytes),
+            "name": "bob.png",
+            "original_name": "bob.png",
+            "owner": "bob",
+        },
+        f"alice:{nested_id}": {
+            "id": nested_id,
+            "path": str(nested_path),
+            "mime": "image/png",
+            "size": len(png_bytes),
+            "name": "nested.png",
+            "original_name": "nested.png",
+            "owner": "alice",
+        },
+    }
+    (storage_base / "uploads.json").write_text(json.dumps(index), encoding="utf-8")
+    monkeypatch.setattr(constants, "UPLOAD_DIR", str(upload_dir))
+
+    handler = UploadHandler(str(tmp_path), str(upload_dir))
+    app = _build_test_app(handler)
+    client = TestClient(app)
+
+    return SimpleNamespace(
+        upload_dir=upload_dir,
+        storage_base=storage_base,
+        alice_id=alice_id,
+        bob_id=bob_id,
+        nested_id=nested_id,
+        png_bytes=png_bytes,
+        handler=handler,
+        app=app,
+        client=client,
+    )
+
+
+# 1. Ordinary upload root
+def test_matrix_01_ordinary_upload_root(tmp_path: Path, monkeypatch):
+    env = _create_fixture_env(tmp_path, monkeypatch, symlinked_root=False)
+    get_res = env.client.get(f"/api/upload/{env.alice_id}")
+    assert get_res.status_code == 200
+    assert get_res.content == env.png_bytes
+
+    head_res = env.client.head(f"/api/upload/{env.alice_id}")
+    assert head_res.status_code == 200
+    assert len(head_res.content) == 0
+
+
+# 2. Upload root that is a symlink to an authorized directory
+def test_matrix_02_symlinked_upload_root(tmp_path: Path, monkeypatch):
+    env = _create_fixture_env(tmp_path, monkeypatch, symlinked_root=True)
+    get_res = env.client.get(f"/api/upload/{env.alice_id}")
+    assert get_res.status_code == 200
+    assert get_res.content == env.png_bytes
+
+    head_res = env.client.head(f"/api/upload/{env.alice_id}")
+    assert head_res.status_code == 200
+    assert len(head_res.content) == 0
+
+
+# 3. Valid file in nested upload directory
+def test_matrix_03_nested_upload_directory(tmp_path: Path, monkeypatch):
+    for symlinked in (False, True):
+        env = _create_fixture_env(tmp_path / f"nested_{symlinked}", monkeypatch, symlinked_root=symlinked)
+        get_res = env.client.get(f"/api/upload/{env.nested_id}")
+        assert get_res.status_code == 200
+        assert get_res.content == env.png_bytes
+
+        head_res = env.client.head(f"/api/upload/{env.nested_id}")
+        assert head_res.status_code == 200
+        assert len(head_res.content) == 0
+
+
+# 4. Symlinked in-root directory resolving safely inside the root
+def test_matrix_04_symlinked_in_root_directory_safe(tmp_path: Path, monkeypatch):
+    env = _create_fixture_env(tmp_path, monkeypatch, symlinked_root=False)
+    real_sub = env.storage_base / "real_sub"
+    real_sub.mkdir(parents=True, exist_ok=True)
+    sub_file_id = "d" * 32 + ".png"
+    (real_sub / sub_file_id).write_bytes(env.png_bytes)
+
+    link_sub = env.storage_base / "link_sub"
+    os.symlink(real_sub, link_sub)
+
+    # Register in uploads.json pointing via symlinked in-root directory
+    uploads_json = env.storage_base / "uploads.json"
+    index = json.loads(uploads_json.read_text(encoding="utf-8"))
+    index[f"alice:{sub_file_id}"] = {
+        "id": sub_file_id,
+        "path": str(link_sub / sub_file_id),
+        "mime": "image/png",
+        "size": len(env.png_bytes),
+        "name": "sub.png",
+        "owner": "alice",
+    }
+    uploads_json.write_text(json.dumps(index), encoding="utf-8")
+
+    get_res = env.client.get(f"/api/upload/{sub_file_id}")
+    assert get_res.status_code == 200
+    assert get_res.content == env.png_bytes
+
+    head_res = env.client.head(f"/api/upload/{sub_file_id}")
+    assert head_res.status_code == 200
+    assert len(head_res.content) == 0
+
+
+# 5. Symlink escaping outside the authorized root — rejected
+def test_matrix_05_symlink_escaping_outside_root_rejected(tmp_path: Path, monkeypatch):
+    env = _create_fixture_env(tmp_path, monkeypatch, symlinked_root=False)
+
+    outside_dir = tmp_path / "outside_store"
+    outside_dir.mkdir(parents=True, exist_ok=True)
+    secret_file = outside_dir / "secret.txt"
+    secret_file.write_text("CONFIDENTIAL_SYSTEM_DATA", encoding="utf-8")
+
+    # A: Direct file symlink escaping root
+    escape_file_id = "e" * 32 + ".txt"
+    os.symlink(secret_file, env.storage_base / escape_file_id)
+
+    uploads_json = env.storage_base / "uploads.json"
+    index = json.loads(uploads_json.read_text(encoding="utf-8"))
+    index[f"alice:{escape_file_id}"] = {
+        "id": escape_file_id,
+        "path": str(env.storage_base / escape_file_id),
+        "mime": "text/plain",
+        "size": len("CONFIDENTIAL_SYSTEM_DATA"),
+        "name": "escape.txt",
+        "owner": "alice",
+    }
+    uploads_json.write_text(json.dumps(index), encoding="utf-8")
+
+    get_res = env.client.get(f"/api/upload/{escape_file_id}")
+    assert get_res.status_code == 403
+    head_res = env.client.head(f"/api/upload/{escape_file_id}")
+    assert head_res.status_code == 403
+    assert len(head_res.content) == 0
+
+    # B: Directory symlink escaping root
+    escape_dir_link = env.storage_base / "evil_sub"
+    os.symlink(outside_dir, escape_dir_link)
+    escape_dir_id = "f" * 32 + ".txt"
+    index[f"alice:{escape_dir_id}"] = {
+        "id": escape_dir_id,
+        "path": str(escape_dir_link / "secret.txt"),
+        "mime": "text/plain",
+        "size": len("CONFIDENTIAL_SYSTEM_DATA"),
+        "name": "escape_sub.txt",
+        "owner": "alice",
+    }
+    uploads_json.write_text(json.dumps(index), encoding="utf-8")
+
+    get_dir = env.client.get(f"/api/upload/{escape_dir_id}")
+    assert get_dir.status_code == 403
+    head_dir = env.client.head(f"/api/upload/{escape_dir_id}")
+    assert head_dir.status_code == 403
+    assert len(head_dir.content) == 0
+
+
+# 6. Malformed upload ID — rejected
+def test_matrix_06_malformed_upload_id_rejected(tmp_path: Path, monkeypatch):
+    env = _create_fixture_env(tmp_path, monkeypatch, symlinked_root=True)
+
+    malformed_ids = [
+        "../../etc/passwd",
+        "..%2f..%2fetc%2fpasswd",
+        "invalid!id@specials",
+        "short_id.png",
+        "g" * 32 + ".png",  # non-hex character 'g'
+        " " + "a" * 32 + ".png",
+        "a" * 31,
+    ]
+    for bad_id in malformed_ids:
+        get_res = env.client.get(f"/api/upload/{bad_id}")
+        assert get_res.status_code in (400, 403, 404), f"GET failed for {bad_id}: {get_res.status_code}"
+        head_res = env.client.head(f"/api/upload/{bad_id}")
+        assert head_res.status_code == get_res.status_code, f"HEAD failed for {bad_id}: {head_res.status_code}"
+        assert len(head_res.content) == 0
+
+
+# 7. Missing upload — rejected
+def test_matrix_07_missing_upload_rejected(tmp_path: Path, monkeypatch):
+    env = _create_fixture_env(tmp_path, monkeypatch, symlinked_root=True)
+    missing_id = "1" * 32 + ".png"
+
+    get_res = env.client.get(f"/api/upload/{missing_id}")
+    assert get_res.status_code == 404
+    head_res = env.client.head(f"/api/upload/{missing_id}")
+    assert head_res.status_code == 404
+    assert len(head_res.content) == 0
+
+
+# 8. Foreign-user upload — rejected
+def test_matrix_08_foreign_user_upload_rejected(tmp_path: Path, monkeypatch):
+    env = _create_fixture_env(tmp_path, monkeypatch, symlinked_root=True)
+
+    # Bob attempts to access Alice's upload
+    bob_get = env.client.get(f"/api/upload/{env.alice_id}", headers={"x-test-user": "bob"})
+    assert bob_get.status_code == 404
+    bob_head = env.client.head(f"/api/upload/{env.alice_id}", headers={"x-test-user": "bob"})
+    assert bob_head.status_code == 404
+    assert len(bob_head.content) == 0
+
+    # Unauthenticated attempts
+    unauth_get = env.client.get(f"/api/upload/{env.alice_id}", headers={"x-test-user": "none"})
+    assert unauth_get.status_code in (401, 403)
+    unauth_head = env.client.head(f"/api/upload/{env.alice_id}", headers={"x-test-user": "none"})
+    assert unauth_head.status_code == unauth_get.status_code
+    assert len(unauth_head.content) == 0
+
+    # Admin access succeeds
+    admin_get = env.client.get(f"/api/upload/{env.alice_id}", headers={"x-test-user": "admin"})
+    assert admin_get.status_code == 200
+    admin_head = env.client.head(f"/api/upload/{env.alice_id}", headers={"x-test-user": "admin"})
+    assert admin_head.status_code == 200
+    assert len(admin_head.content) == 0
+
+
+# 9. Valid GET/HEAD parity on both ordinary and symlinked roots
+def test_matrix_09_get_head_parity(tmp_path: Path, monkeypatch):
+    for symlinked in (False, True):
+        env = _create_fixture_env(tmp_path / f"parity_{symlinked}", monkeypatch, symlinked_root=symlinked)
+        get_res = env.client.get(f"/api/upload/{env.alice_id}")
+        head_res = env.client.head(f"/api/upload/{env.alice_id}")
+
+        assert get_res.status_code == 200
+        assert head_res.status_code == 200
+        assert len(head_res.content) == 0
+        assert get_res.headers.get("x-content-type-options") == "nosniff"
+        assert head_res.headers.get("x-content-type-options") == "nosniff"
+        assert get_res.headers.get("content-type") == head_res.headers.get("content-type")
+        assert get_res.headers.get("content-length") == head_res.headers.get("content-length")
+
+
+# 10. Cached, missing and stale thumbnail HEAD behavior
+def test_matrix_10_thumbnail_head_behavior(tmp_path: Path, monkeypatch):
+    env = _create_fixture_env(tmp_path, monkeypatch, symlinked_root=True)
+    thumb_path = env.storage_base / ".thumbs" / f"{env.alice_id}.jpg"
+
+    from unittest.mock import patch
+
+    # Case A: Missing thumbnail
+    assert not thumb_path.exists()
+    with patch("PIL.Image.open", side_effect=AssertionError("HEAD must not decode")):
+        head_missing = env.client.head(f"/api/upload/{env.alice_id}?thumb=1")
+    assert head_missing.status_code == 200
+    assert len(head_missing.content) == 0
+    # Must NOT generate thumbnail on disk during HEAD
+    assert not thumb_path.exists()
+    # Must NOT advertise Content-Length when thumbnail is ungenerated
+    assert "content-length" not in head_missing.headers
+
+    # Generate thumbnail via GET
+    get_gen = env.client.get(f"/api/upload/{env.alice_id}?thumb=1")
+    assert get_gen.status_code == 200
+    assert thumb_path.exists()
+    thumb_mtime = os.path.getmtime(thumb_path)
+
+    # Case B: Cached (fresh) thumbnail
+    with patch("PIL.Image.open", side_effect=AssertionError("HEAD must not decode")):
+        head_cached = env.client.head(f"/api/upload/{env.alice_id}?thumb=1")
+    assert head_cached.status_code == 200
+    assert len(head_cached.content) == 0
+    assert head_cached.headers.get("content-type") == "image/jpeg"
+    assert "content-length" in head_cached.headers
+    assert head_cached.headers["content-length"] == str(len(thumb_path.read_bytes()))
+    # Mtime did not change
+    assert os.path.getmtime(thumb_path) == thumb_mtime
+
+    # Case C: Stale thumbnail (original modified after thumb)
+    alice_file = env.storage_base / env.alice_id
+    future_time = time.time() + 100
+    os.utime(alice_file, (future_time, future_time))
+
+    with patch("PIL.Image.open", side_effect=AssertionError("HEAD must not decode")):
+        head_stale = env.client.head(f"/api/upload/{env.alice_id}?thumb=1")
+    assert head_stale.status_code == 200
+    assert len(head_stale.content) == 0
+    # Must NOT advertise old stale Content-Length
+    assert "content-length" not in head_stale.headers
+    # Must NOT regenerate thumb during HEAD
+    assert os.path.getmtime(thumb_path) == thumb_mtime
+
+
+# 11. No directory traversal or unauthorized file disclosure
+def test_matrix_11_directory_traversal_prevention(tmp_path: Path, monkeypatch):
+    env = _create_fixture_env(tmp_path, monkeypatch, symlinked_root=True)
+
+    secret = tmp_path / "system_secret.txt"
+    secret.write_text("SENSITIVE_KEY_VALUE", encoding="utf-8")
+
+    traversal_paths = [
+        f"/api/upload/..%2f..%2f{secret.name}",
+        f"/api/upload/%2e%2e%2f%2e%2e%2f{secret.name}",
+        f"/api/upload/../../{secret.name}",
+        f"/api/upload/{env.alice_id}/../../{secret.name}",
+    ]
+    for target in traversal_paths:
+        res = env.client.get(target)
+        assert res.status_code in (400, 403, 404)
+        assert "SENSITIVE_KEY_VALUE" not in res.text