diff --git a/backend/app/utils/sidecar.py b/backend/app/utils/sidecar.py
index ae35b28..8df78b4 100644
--- a/backend/app/utils/sidecar.py
+++ b/backend/app/utils/sidecar.py
@@ -4,6 +4,7 @@ No per-platform branching: a small common key set with fallbacks; the
 full JSON is kept in raw so anything unmapped is recoverable later.
 """
 
+import re
 from dataclasses import dataclass
 from datetime import UTC, datetime
 from pathlib import Path
@@ -21,10 +22,28 @@ class SidecarData:
     raw: dict
 
 
+# gallery-dl prefixes media filenames with `NN_` for in-post ordering
+# (`01_HOLLOW-ICHIGO.png`, `02_HOLOW ICHIGO.zip`) but writes the sidecar
+# under the attachment's stem WITHOUT that ordering prefix
+# (`HOLLOW-ICHIGO.json`). Strip the prefix when looking for sidecars.
+# Confirmed against real Patreon downloads 2026-05-26 — without this
+# strip, every gallery-dl post-level sidecar was invisible to FC since
+# FC-3 shipped (24 deep-refresh calls produced 0 Posts in operator's DB).
+_NUMBERING_PREFIX = re.compile(r"^\d+_(.+)$")
+
+
 def find_sidecar(media: Path) -> Path | None:
+    # Attachment-level sidecars (image.jpg.json, image.json).
     for cand in (media.with_suffix(".json"), Path(str(media) + ".json")):
         if cand.is_file():
             return cand
+    # gallery-dl post-numbered convention: strip the `NN_` prefix from
+    # the stem and look for that.json in the same directory.
+    m = _NUMBERING_PREFIX.match(media.stem)
+    if m:
+        cand = media.parent / f"{m.group(1)}.json"
+        if cand.is_file():
+            return cand
     return None
 
 
diff --git a/tests/test_sidecar_util.py b/tests/test_sidecar_util.py
index 0fd3e40..3abff31 100644
--- a/tests/test_sidecar_util.py
+++ b/tests/test_sidecar_util.py
@@ -23,6 +23,51 @@ def test_find_sidecar_none(tmp_path):
     assert find_sidecar(media) is None
 
 
+def test_find_sidecar_gallerydl_numbered_prefix(tmp_path):
+    """gallery-dl prefixes media filenames with NN_ for in-post ordering
+    (e.g. `01_HOLLOW-ICHIGO.png`) but writes the post-level sidecar under
+    the attachment stem WITHOUT the prefix (`HOLLOW-ICHIGO.json`).
+    Confirmed against real Patreon downloads 2026-05-26 — operator's deep
+    scan produced 24 refresh calls but 0 Posts because the unprefixed
+    sidecar was invisible to find_sidecar."""
+    media = tmp_path / "01_HOLLOW-ICHIGO.png"
+    media.write_bytes(b"x")
+    sc = tmp_path / "HOLLOW-ICHIGO.json"
+    sc.write_text("{}")
+    assert find_sidecar(media) == sc
+
+
+def test_find_sidecar_multidigit_prefix(tmp_path):
+    """Numbering prefix can be wider than 2 digits (`001_...`); the strip
+    handles any \\d+_ form."""
+    media = tmp_path / "001_mirko-sketch.png"
+    media.write_bytes(b"x")
+    sc = tmp_path / "mirko-sketch.json"
+    sc.write_text("{}")
+    assert find_sidecar(media) == sc
+
+
+def test_find_sidecar_prefers_attachment_level_over_post_level(tmp_path):
+    """If BOTH a per-attachment sidecar and a post-level sidecar exist,
+    the attachment-level one wins (it's more specific)."""
+    media = tmp_path / "01_image.png"
+    media.write_bytes(b"x")
+    per_attachment = tmp_path / "01_image.json"
+    per_attachment.write_text('{"specific": true}')
+    post_level = tmp_path / "image.json"
+    post_level.write_text('{"specific": false}')
+    assert find_sidecar(media) == per_attachment
+
+
+def test_find_sidecar_no_underscore_not_treated_as_prefix(tmp_path):
+    """`01.png` (just digits, no underscore-separated stem) shouldn't
+    match. The regex requires NN_<something>."""
+    media = tmp_path / "01.png"
+    media.write_bytes(b"x")
+    (tmp_path / ".json").write_text("{}")  # would be matched only if buggy
+    assert find_sidecar(media) is None
+
+
 def test_parse_empty_dict_all_none():
     sd = parse_sidecar({})
     assert isinstance(sd, SidecarData)