diff --git a/pipeline/fetch/src/drive_fetch.py b/pipeline/fetch/src/drive_fetch.py
index b1b0dbb..6ca3506 100644
--- a/pipeline/fetch/src/drive_fetch.py
+++ b/pipeline/fetch/src/drive_fetch.py
@@ -240,9 +240,45 @@ def ext_for(cfg: Config, d: dict, mime: str) -> tuple[str | None, str]:
     return None, (os.path.splitext(name)[1] or ".bin")
 
 
+def sidecar_name(fid: str) -> str:
+    """The metadata sidecar's filename — the on-disk contract clean reads. Single-sourced."""
+    return f"{fid}.json"
+
+
+def content_name(cfg: Config, d: dict, mime: str, fid: str) -> tuple[str | None, str]:
+    """(export_format|None, on-disk content filename), disambiguated from the sidecar so content
+    can never overwrite <fid>.json. Compared case-insensitively for case-folding filesystems
+    (macOS APFS, Windows, Docker Desktop bind mounts), where <fid>.JSON == <fid>.json."""
+    fmt, ext = ext_for(cfg, d, mime)
+    name = f"{fid}{ext}"
+    if name.lower() == sidecar_name(fid).lower():
+        name = f"{fid}.data{ext}"
+    return fmt, name
+
+
+def _clobbered_by_sidecar(cfg: Config, fid: str, prev_local: str | None) -> bool:
+    """True if the manifest's content path IS the sidecar file — its bytes were overwritten by the
+    sidecar write (the pre-.data.json bug), so the entry must re-download to heal. Decided by file
+    identity, not name: an exact sidecar-name localPath is always the clobber; a case-variant (e.g.
+    <fid>.JSON) is the clobber only on a case-folding filesystem, where it resolves to the same file
+    as the sidecar — on a case-sensitive one it is a distinct, valid content file that must be kept
+    (else it would be needlessly re-downloaded and orphaned)."""
+    if not prev_local:
+        return False
+    sidecar = sidecar_name(fid)
+    if prev_local == sidecar:
+        return True
+    if prev_local.lower() != sidecar.lower():
+        return False
+    try:
+        return (cfg.raw_dir / prev_local).samefile(cfg.raw_dir / sidecar)
+    except OSError:  # content or sidecar missing -> not a live clobber; let the exists() skip re-fetch
+        return False
+
+
 def merge_sidecar_lineage(cfg: Config, fid: str, lineage: dict) -> None:
     """Adds lineage paths to an existing sidecar without touching the rest of its metadata."""
-    sidecar = cfg.raw_dir / f"{fid}.json"
+    sidecar = cfg.raw_dir / sidecar_name(fid)
     meta: object = {}
     if sidecar.exists():
         try:
@@ -256,13 +292,11 @@ def merge_sidecar_lineage(cfg: Config, fid: str, lineage: dict) -> None:
 
 
 def download_file(cfg: Config, d: dict, fid: str, mime: str, lineage: dict) -> str:
-    """Downloads to raw/<fid><ext> (atomically) + a metadata sidecar. Returns the local name.
-    `.json` content is stored as <fid>.data.json — <fid>.json IS the sidecar."""
-    fmt, ext = ext_for(cfg, d, mime)
-    if ext == ".json":
-        ext = ".data.json"
-    out = cfg.raw_dir / f"{fid}{ext}"
-    tmp = cfg.raw_dir / f".tmp-{fid}{ext}"
+    """Downloads to raw/<content-name> (atomically) + a metadata sidecar. Returns the local name.
+    The content name is disambiguated from the sidecar (<fid>.json) so the two never collide."""
+    fmt, name = content_name(cfg, d, mime, fid)
+    out = cfg.raw_dir / name
+    tmp = cfg.raw_dir / f".tmp-{name}"
     args = ["drive", "download", fid, "--out", str(tmp)]
     if fmt:
         args += ["--format", fmt]
@@ -274,12 +308,12 @@ def download_file(cfg: Config, d: dict, fid: str, mime: str, lineage: dict) -> s
         meta = meta["file"]
     if isinstance(meta, dict):
         meta.update(lineage)
-    write_atomic(cfg.raw_dir / f"{fid}.json", json.dumps(meta, indent=2, ensure_ascii=False).encode())
+    write_atomic(cfg.raw_dir / sidecar_name(fid), json.dumps(meta, indent=2, ensure_ascii=False).encode())
     return out.name
 
 
 def remove_local(cfg: Config, entry: dict, fid: str) -> None:
-    for p in (entry.get("localPath"), f"{fid}.json"):
+    for p in (entry.get("localPath"), sidecar_name(fid)):
         if p and (cfg.raw_dir / p).exists():
             (cfg.raw_dir / p).unlink()
 
@@ -349,10 +383,12 @@ def sync_once(cfg: Config, folder_id: str) -> dict:
             "parentPath": f"/{cfg.folder or folder_id}",
             "parentIds": parents(d),
         })
-        # A localPath equal to the sidecar means the content was clobbered by the sidecar write
-        # (pre-.data.json state): never treat it as a valid mirror — re-download to heal.
-        if (prev and prev.get("fingerprint") == fp and prev_local
-                and prev_local != f"{fid}.json" and (cfg.raw_dir / prev_local).exists()):
+        # A localPath that is really the sidecar file is a pre-.data.json entry whose content the
+        # sidecar write clobbered: treat it as absent so the file re-downloads and heals, and so the
+        # rename-cleanup below never unlinks the freshly written sidecar.
+        if _clobbered_by_sidecar(cfg, fid, prev_local):
+            prev_local = None
+        if prev and prev.get("fingerprint") == fp and prev_local and (cfg.raw_dir / prev_local).exists():
             # Backfill/refresh path metadata without redownloading unchanged files.
             touched = False
             for k, v in lineage.items():
@@ -375,9 +411,7 @@ def sync_once(cfg: Config, folder_id: str) -> dict:
             continue
         # a rename or export-format change alters the local name: drop the previous file so its
         # stale content isn't orphaned in the mirror (deletion later only removes the current name).
-        # Never unlink <fid>.json — that is the sidecar (a healing entry's prev_local points at it).
-        if (prev_local and prev_local != local and prev_local != f"{fid}.json"
-                and (cfg.raw_dir / prev_local).exists()):
+        if prev_local and prev_local != local and (cfg.raw_dir / prev_local).exists():
             (cfg.raw_dir / prev_local).unlink()
         manifest[fid] = {
             "name": _field(d, "name", "title", default=""),
diff --git a/pipeline/fetch/tests/test_drive_fetch.py b/pipeline/fetch/tests/test_drive_fetch.py
index 1359888..84b3b45 100644
--- a/pipeline/fetch/tests/test_drive_fetch.py
+++ b/pipeline/fetch/tests/test_drive_fetch.py
@@ -106,6 +106,23 @@ def test_write_atomic_and_sidecar_merge(tmp_path):
     assert json.loads((tmp_path / "F.json").read_text()) == {"kept": True, "drivePath": "/X/a.pdf"}
 
 
+def test_clobbered_by_sidecar_uses_file_identity_not_name(tmp_path, monkeypatch):
+    """The clobber is decided by file identity, not name: an exact sidecar-name localPath is always
+    the clobber, but a case-variant (<fid>.JSON) is the clobber ONLY on a case-folding filesystem
+    (where it resolves to the sidecar). On a case-sensitive filesystem it is a distinct valid file
+    that must be kept, else it is needlessly re-downloaded and orphaned."""
+    cfg = _cfg(tmp_path)
+    (tmp_path / "C.json").write_text("{}")                      # the sidecar
+    assert df._clobbered_by_sidecar(cfg, "C", None) is False
+    assert df._clobbered_by_sidecar(cfg, "C", "C.json") is True     # exact name -> always clobber
+    assert df._clobbered_by_sidecar(cfg, "C", "C.pdf") is False     # unrelated content -> never
+    # case-variant name: outcome follows the filesystem, probed via samefile
+    monkeypatch.setattr(df.Path, "samefile", lambda self, other: False)   # case-sensitive fs
+    assert df._clobbered_by_sidecar(cfg, "C", "C.JSON") is False    # distinct file -> keep it
+    monkeypatch.setattr(df.Path, "samefile", lambda self, other: True)    # case-folding fs
+    assert df._clobbered_by_sidecar(cfg, "C", "C.JSON") is True     # same file -> heal
+
+
 # ── folder resolution ────────────────────────────────────────────────────────
 def test_resolve_folder_id_explicit_wins(tmp_path):
     assert df.resolve_folder_id(_cfg(tmp_path, folder_id="explicit-id")) == "explicit-id"
@@ -262,6 +279,20 @@ def test_sync_once_json_content_does_not_collide_with_sidecar(sync_env):
     assert manifest["C"]["localPath"] == "C.data.json"
 
 
+def test_sync_once_uppercase_json_content_does_not_collide_with_sidecar(sync_env):
+    """The collision is case-insensitive: on a case-folding filesystem (macOS APFS, Windows,
+    Docker Desktop bind mounts) <fid>.JSON and the sidecar <fid>.json are the same file, so an
+    uppercase-extension JSON must also be routed to <fid>.data.JSON."""
+    cfg, tmp_path, fake = sync_env
+    fake.items.append({"id": "C", "name": "CONFIG.JSON", "mimeType": "application/json",
+                       "modifiedTime": "t1", "parents": ["folder1"]})
+    df.sync_once(cfg, "root")
+    assert (tmp_path / "C.data.JSON").read_text() == "content-C"
+    assert json.loads((tmp_path / "C.json").read_text())["id"] == "C"   # sidecar not clobbered
+    manifest = json.loads((tmp_path / "_state.json").read_text())["files"]
+    assert manifest["C"]["localPath"] == "C.data.JSON"
+
+
 def test_sync_once_heals_json_entry_clobbered_by_sidecar(sync_env):
     """A pre-fix manifest whose localPath points at the sidecar must re-download the content
     (even with an unchanged fingerprint) and must not delete the sidecar while healing."""