diff --git a/backend/app/services/artist_directory_service.py b/backend/app/services/artist_directory_service.py
index a16c1aa..eda9afc 100644
--- a/backend/app/services/artist_directory_service.py
+++ b/backend/app/services/artist_directory_service.py
@@ -127,17 +127,20 @@ class ArtistDirectoryService:
                 ImageRecord.artist_id.label("artist_id"),
                 ImageRecord.sha256.label("sha256"),
                 ImageRecord.mime.label("mime"),
+                ImageRecord.thumbnail_path.label("thumbnail_path"),
                 rn,
             )
             .where(ImageRecord.artist_id.in_(artist_ids))
             .subquery()
         )
         stmt = (
-            select(sub.c.artist_id, sub.c.sha256, sub.c.mime)
+            select(
+                sub.c.artist_id, sub.c.sha256, sub.c.mime, sub.c.thumbnail_path,
+            )
             .where(sub.c.rn <= _PREVIEW_COUNT)
             .order_by(sub.c.artist_id, sub.c.rn)
         )
         out: dict[int, list[str]] = {}
-        for aid, sha, mime in (await self.session.execute(stmt)).all():
-            out.setdefault(aid, []).append(thumbnail_url(sha, mime))
+        for aid, sha, mime, tp in (await self.session.execute(stmt)).all():
+            out.setdefault(aid, []).append(thumbnail_url(tp, sha, mime))
         return out
diff --git a/backend/app/services/artist_service.py b/backend/app/services/artist_service.py
index c6aff2b..56f19ff 100644
--- a/backend/app/services/artist_service.py
+++ b/backend/app/services/artist_service.py
@@ -198,7 +198,7 @@ class ArtistService:
                     "mime": r.mime,
                     "width": r.width,
                     "height": r.height,
-                    "thumbnail_url": thumbnail_url(r.sha256, r.mime),
+                    "thumbnail_url": thumbnail_url(r.thumbnail_path, r.sha256, r.mime),
                 }
                 for r in rows
             ],
diff --git a/backend/app/services/gallery_service.py b/backend/app/services/gallery_service.py
index 0a46fec..095890d 100644
--- a/backend/app/services/gallery_service.py
+++ b/backend/app/services/gallery_service.py
@@ -90,9 +90,27 @@ class TimelineBucket:
     count: int
 
 
-def thumbnail_url(sha256_hex: str, mime: str) -> str:
-    # Quart serves /images/* via the frontend blueprint (FC-1); thumbnails go
-    # under /images/thumbs/. The MIME determines the extension.
+def thumbnail_url(thumbnail_path: str | None, sha256_hex: str, mime: str) -> str:
+    """Return the URL to fetch a thumbnail.
+
+    Prefers the stored thumbnail_path verbatim — Quart serves /images/*
+    1:1 from the volume (frontend.py:20-36), so the URL IS the disk
+    path. Falls back to deriving from (sha256, mime) only when the
+    record's thumbnail_path is NULL (thumbnailer hasn't run yet); that
+    URL will 404 until backfill catches it, same as before the path
+    was tracked.
+
+    Pre-2026-05-30 this was derived only from (sha256, mime), which
+    disagreed with the actual on-disk extension when the thumbnailer
+    chose its format from transparency rather than MIME — every PNG
+    source without alpha (extension was .jpg on disk) and every WebP
+    source with alpha (extension was .png on disk) silently 404'd
+    despite the thumbnail file existing.
+    """
+    if thumbnail_path:
+        return thumbnail_path
+    # Fallback for records with no thumbnail recorded yet — preserves
+    # prior behavior (URL exists but 404s until backfill regenerates).
     ext = ".png" if mime in ("image/png", "image/gif") else ".jpg"
     bucket = sha256_hex[:3]
     return f"/images/thumbs/{bucket}/{sha256_hex}{ext}"
@@ -198,7 +216,7 @@ class GalleryService:
                 created_at=record.created_at,
                 effective_date=eff_date,
                 posted_at=posted_at,
-                thumbnail_url=thumbnail_url(record.sha256, record.mime),
+                thumbnail_url=thumbnail_url(record.thumbnail_path, record.sha256, record.mime),
                 artist=artists.get(record.id),
             )
             for record, posted_at, eff_date in rows
@@ -306,7 +324,7 @@ class GalleryService:
             "integrity_status": record.integrity_status,
             "created_at": record.created_at.isoformat(),
             "posted_at": posted_at.isoformat() if posted_at else None,
-            "thumbnail_url": thumbnail_url(record.sha256, record.mime),
+            "thumbnail_url": thumbnail_url(record.thumbnail_path, record.sha256, record.mime),
             "image_url": f"/images/{record.path.split('/images/', 1)[-1]}",
             "artist": (
                 {"id": artist.id, "name": artist.name, "slug": artist.slug}
diff --git a/backend/app/services/post_feed_service.py b/backend/app/services/post_feed_service.py
index 319d645..634cfd3 100644
--- a/backend/app/services/post_feed_service.py
+++ b/backend/app/services/post_feed_service.py
@@ -207,6 +207,7 @@ class PostFeedService:
                 ImageRecord.primary_post_id,
                 ImageRecord.sha256,
                 ImageRecord.mime,
+                ImageRecord.thumbnail_path,
                 func.row_number().over(
                     partition_by=ImageRecord.primary_post_id,
                     order_by=ImageRecord.id.asc(),
@@ -220,18 +221,18 @@ class PostFeedService:
         )
         stmt = select(
             ranked.c.id, ranked.c.primary_post_id,
-            ranked.c.sha256, ranked.c.mime, ranked.c.total,
+            ranked.c.sha256, ranked.c.mime, ranked.c.thumbnail_path, ranked.c.total,
         )
         if limit is not None:
             stmt = stmt.where(ranked.c.rn <= limit)
         rows = (await self.session.execute(stmt)).all()
 
         out: dict[int, dict] = {pid: {"thumbs": [], "more": 0} for pid in post_ids}
-        for img_id, pid, sha, mime, total in rows:
+        for img_id, pid, sha, mime, tp, total in rows:
             entry = out.setdefault(pid, {"thumbs": [], "more": 0})
             entry["thumbs"].append({
                 "image_id": img_id,
-                "thumbnail_url": thumbnail_url(sha, mime),
+                "thumbnail_url": thumbnail_url(tp, sha, mime),
                 "mime": mime,
             })
             # `total` is constant per partition; overflow = total - THUMBNAIL_LIMIT.
diff --git a/backend/app/services/series_service.py b/backend/app/services/series_service.py
index 6ed3df8..361caa5 100644
--- a/backend/app/services/series_service.py
+++ b/backend/app/services/series_service.py
@@ -63,6 +63,7 @@ class SeriesService:
                     ImageRecord.sha256,
                     ImageRecord.mime,
                     ImageRecord.path,
+                    ImageRecord.thumbnail_path,
                 )
                 .join(ImageRecord, ImageRecord.id == SeriesPage.image_id)
                 .where(SeriesPage.series_tag_id == series_tag_id)
@@ -75,7 +76,7 @@ class SeriesService:
                 {
                     "image_id": r.image_id,
                     "page_number": r.page_number,
-                    "thumbnail_url": thumbnail_url(r.sha256, r.mime),
+                    "thumbnail_url": thumbnail_url(r.thumbnail_path, r.sha256, r.mime),
                     "image_url": f"/images/{r.path.split('/images/', 1)[-1]}",
                 }
                 for r in rows
diff --git a/backend/app/services/showcase_service.py b/backend/app/services/showcase_service.py
index b45e0b5..f34051b 100644
--- a/backend/app/services/showcase_service.py
+++ b/backend/app/services/showcase_service.py
@@ -34,7 +34,7 @@ class ShowcaseService:
                 "mime": r.mime,
                 "width": r.width,
                 "height": r.height,
-                "thumbnail_url": thumbnail_url(r.sha256, r.mime),
+                "thumbnail_url": thumbnail_url(r.thumbnail_path, r.sha256, r.mime),
             }
             for r in rows
         ]
diff --git a/backend/app/services/tag_directory_service.py b/backend/app/services/tag_directory_service.py
index a0ffaaa..c88b04c 100644
--- a/backend/app/services/tag_directory_service.py
+++ b/backend/app/services/tag_directory_service.py
@@ -115,12 +115,17 @@ class TagDirectoryService:
             .subquery()
         )
         stmt = (
-            select(sub.c.tag_id, ImageRecord.sha256, ImageRecord.mime)
+            select(
+                sub.c.tag_id,
+                ImageRecord.sha256,
+                ImageRecord.mime,
+                ImageRecord.thumbnail_path,
+            )
             .join(ImageRecord, ImageRecord.id == sub.c.image_record_id)
             .where(sub.c.rn <= 3)
             .order_by(sub.c.tag_id, sub.c.rn)
         )
         out: dict[int, list[str]] = {}
-        for tag_id, sha, mime in (await self.session.execute(stmt)).all():
-            out.setdefault(tag_id, []).append(thumbnail_url(sha, mime))
+        for tag_id, sha, mime, tp in (await self.session.execute(stmt)).all():
+            out.setdefault(tag_id, []).append(thumbnail_url(tp, sha, mime))
         return out