diff --git a/app/assets/api/routes.py b/app/assets/api/routes.py
index 68126b6a5..1155fa503 100644
--- a/app/assets/api/routes.py
+++ b/app/assets/api/routes.py
@@ -401,12 +401,16 @@ async def upload_asset(request: web.Request) -> web.Response:
         )
 
     if spec.tags and spec.tags[0] == "models":
+        # tag[1] may be the standalone category ("checkpoints") or the
+        # slash-joined shape ("checkpoints/flux/...") that
+        # `get_name_and_tags_from_asset_path` and cloud both emit. Match
+        # `resolve_destination_from_tags` by extracting the first segment.
+        category = spec.tags[1].split("/", 1)[0] if len(spec.tags) >= 2 else ""
         if (
             len(spec.tags) < 2
-            or spec.tags[1] not in folder_paths.folder_names_and_paths
+            or category not in folder_paths.folder_names_and_paths
         ):
             delete_temp_file_if_exists(parsed.tmp_path)
-            category = spec.tags[1] if len(spec.tags) >= 2 else ""
             return _build_error_response(
                 400, "INVALID_BODY", f"unknown models category '{category}'"
             )
diff --git a/app/assets/database/queries/tags.py b/app/assets/database/queries/tags.py
index 2501665ac..c891364b4 100644
--- a/app/assets/database/queries/tags.py
+++ b/app/assets/database/queries/tags.py
@@ -21,7 +21,12 @@ from app.assets.database.queries.common import (
     build_visible_owner_clause,
     iter_row_chunks,
 )
-from app.assets.helpers import escape_sql_like_string, get_utc_now, normalize_tags
+from app.assets.helpers import (
+    escape_sql_like_string,
+    expand_bucket_prefixes,
+    get_utc_now,
+    normalize_tags,
+)
 
 
 @dataclass(frozen=True)
@@ -96,7 +101,7 @@ def set_reference_tags(
     tags: Sequence[str],
     origin: str = "manual",
 ) -> SetTagsResult:
-    desired = normalize_tags(tags)
+    desired = expand_bucket_prefixes(normalize_tags(tags))
 
     current = set(get_reference_tags(session, reference_id))
 
@@ -149,7 +154,7 @@ def add_tags_to_reference(
         if not ref:
             raise ValueError(f"AssetReference {reference_id} not found")
 
-    norm = normalize_tags(tags)
+    norm = expand_bucket_prefixes(normalize_tags(tags))
     if not norm:
         total = get_reference_tags(session, reference_id=reference_id)
         return AddTagsResult(added=[], already_present=[], total_tags=total)
diff --git a/app/assets/helpers.py b/app/assets/helpers.py
index 3798f3933..2f9e9a0ce 100644
--- a/app/assets/helpers.py
+++ b/app/assets/helpers.py
@@ -47,6 +47,50 @@ def normalize_tags(tags: list[str] | None) -> list[str]:
     return list(dict.fromkeys(t.strip().lower() for t in (tags or []) if (t or "").strip()))
 
 
+def _known_bucket_prefixes() -> set[str]:
+    """Lowercased model-category names eligible for standalone-prefix
+    expansion. Tags whose first slash segment matches one of these get
+    the bucket inserted as a separate token, so FE filters like
+    ``include_tags=models,checkpoints`` keep matching even when the
+    asset lives in a nested subfolder (`models/checkpoints/flux/foo`).
+
+    Bare user labels with slashes whose first segment is not a registered
+    bucket (e.g. ``my-org/team-a``) pass through unchanged.
+    """
+    try:
+        import folder_paths
+
+        return {
+            name.lower()
+            for name in folder_paths.folder_names_and_paths.keys()
+            if name != "custom_nodes"
+        }
+    except Exception:
+        return set()
+
+
+def expand_bucket_prefixes(tags: list[str]) -> list[str]:
+    """Insert standalone bucket tokens after any slash-joined tag whose
+    first segment is a registered model category. Preserves caller order
+    and is idempotent (existing bucket tokens are not duplicated).
+    """
+    if not tags:
+        return list(tags)
+    buckets = _known_bucket_prefixes()
+    if not buckets:
+        return list(tags)
+    seen = set(tags)
+    result: list[str] = []
+    for t in tags:
+        result.append(t)
+        if "/" in t:
+            prefix = t.split("/", 1)[0]
+            if prefix.lower() in buckets and prefix not in seen:
+                result.append(prefix)
+                seen.add(prefix)
+    return result
+
+
 def validate_blake3_hash(s: str) -> str:
     """Validate and normalize a blake3 hash string.
 
diff --git a/app/assets/services/bulk_ingest.py b/app/assets/services/bulk_ingest.py
index 7c673632f..a5ff19c6b 100644
--- a/app/assets/services/bulk_ingest.py
+++ b/app/assets/services/bulk_ingest.py
@@ -13,13 +13,14 @@ from app.assets.database.queries import (
     bulk_insert_references_ignore_conflicts,
     bulk_insert_tags_and_meta,
     delete_assets_by_ids,
+    ensure_tags_exist,
     get_existing_asset_ids,
     get_reference_ids_by_ids,
     get_references_by_paths_and_asset_ids,
     get_unreferenced_unhashed_asset_ids,
     restore_references_by_paths,
 )
-from app.assets.helpers import get_utc_now
+from app.assets.helpers import expand_bucket_prefixes, get_utc_now
 
 if TYPE_CHECKING:
     from app.assets.services.metadata_extract import ExtractedMetadata
@@ -239,7 +240,8 @@ def batch_insert_seed_assets(
             # this, every tag in a bulk-insert batch shares current_time and
             # the tag_name tiebreaker sorts them alphabetically — putting the
             # subpath tag ahead of "models" since "c"/"d"/"l" < "m".
-            for tag_idx, tag in enumerate(ref_data["tags"]):
+            ref_tags = expand_bucket_prefixes(ref_data["tags"])
+            for tag_idx, tag in enumerate(ref_tags):
                 tag_rows.append(
                     {
                         "asset_reference_id": ref_id,
@@ -267,6 +269,16 @@ def batch_insert_seed_assets(
                     }
                 )
 
+    if tag_rows:
+        # Bucket-prefix expansion may have introduced tags the caller did
+        # not register via the upstream tag_pool (e.g. `checkpoints` for a
+        # nested `checkpoints/flux/foo` path). Pre-register the full set so
+        # the AssetReferenceTag.tag_name FK is satisfied; the underlying
+        # insert is ON CONFLICT DO NOTHING so re-registration is idempotent.
+        ensure_tags_exist(
+            session, {row["tag_name"] for row in tag_rows}, tag_type="user"
+        )
+
     bulk_insert_tags_and_meta(session, tag_rows=tag_rows, meta_rows=metadata_rows)
 
     return BulkInsertResult(
diff --git a/tests-unit/assets_test/queries/test_asset_info.py b/tests-unit/assets_test/queries/test_asset_info.py
index 784030ba4..9d75fd42d 100644
--- a/tests-unit/assets_test/queries/test_asset_info.py
+++ b/tests-unit/assets_test/queries/test_asset_info.py
@@ -197,7 +197,10 @@ class TestTagRetrievalOrder:
         result = fetch_reference_asset_and_tags(session, ref.id)
         assert result is not None
         _, _, tags = result
-        assert tags == ["models", "diffusers/kolors/text_encoder"]
+        # Bucket-prefix expansion appends the standalone `diffusers` token
+        # at path-tier (microsecond stagger) so FE set-membership filters
+        # match nested category paths.
+        assert tags == ["models", "diffusers/kolors/text_encoder", "diffusers"]
 
     def test_add_tags_to_reference_lands_after_path_tags(self, session: Session):
         ref = self._make_ref(session)
@@ -256,7 +259,14 @@ class TestTagRetrievalOrder:
         session.commit()
 
         _, tag_map, _ = list_references_page(session)
-        assert tag_map[ref.id] == ["models", "loras/my/custom/path", "second-tag"]
+        # `loras` is expanded from the nested category path; user-added
+        # tags trail behind it via the microsecond stagger.
+        assert tag_map[ref.id] == [
+            "models",
+            "loras/my/custom/path",
+            "loras",
+            "second-tag",
+        ]
 
 
 class TestFetchReferenceAssetAndTags:
diff --git a/tests-unit/assets_test/queries/test_tags.py b/tests-unit/assets_test/queries/test_tags.py
index 4ed99aa37..bf71d2962 100644
--- a/tests-unit/assets_test/queries/test_tags.py
+++ b/tests-unit/assets_test/queries/test_tags.py
@@ -160,6 +160,120 @@ class TestAddTagsToReference:
             add_tags_to_reference(session, reference_id="nonexistent", tags=["x"])
 
 
+class TestBucketPrefixExpansion:
+    """The standalone bucket token must appear in the asset's tag set for
+    nested category paths so FE filters like
+    `include_tags=models,checkpoints` continue to match.
+    """
+
+    def test_set_reference_tags_inserts_bucket_for_nested_path(
+        self, session: Session
+    ):
+        asset = _make_asset(session, "hash-nested")
+        ref = _make_reference(session, asset)
+
+        result = set_reference_tags(
+            session,
+            reference_id=ref.id,
+            tags=["models", "checkpoints/flux"],
+        )
+        session.commit()
+
+        assert set(result.total) == {"models", "checkpoints/flux", "checkpoints"}
+        stored = get_reference_tags(session, reference_id=ref.id)
+        # tag[1] keeps the slash-joined positional contract; the standalone
+        # bucket lands after it via path-tier microsecond stagger so user
+        # tags remain at the tail.
+        assert stored[:3] == ["models", "checkpoints/flux", "checkpoints"]
+
+    def test_set_reference_tags_idempotent_on_replay(self, session: Session):
+        asset = _make_asset(session, "hash-replay")
+        ref = _make_reference(session, asset)
+
+        set_reference_tags(
+            session,
+            reference_id=ref.id,
+            tags=["models", "checkpoints/flux"],
+        )
+        # Replay with the same caller-supplied set; expansion is already
+        # baked in, so nothing should be added or removed.
+        result = set_reference_tags(
+            session,
+            reference_id=ref.id,
+            tags=["models", "checkpoints/flux"],
+        )
+        session.commit()
+
+        assert result.added == []
+        assert result.removed == []
+        assert set(result.total) == {"models", "checkpoints/flux", "checkpoints"}
+
+    def test_add_tags_to_reference_expands_bucket(self, session: Session):
+        asset = _make_asset(session, "hash-add")
+        ref = _make_reference(session, asset)
+
+        result = add_tags_to_reference(
+            session,
+            reference_id=ref.id,
+            tags=["loras/style/v2"],
+        )
+        session.commit()
+
+        assert set(result.added) == {"loras/style/v2", "loras"}
+        stored = get_reference_tags(session, reference_id=ref.id)
+        assert "loras" in stored
+        assert "loras/style/v2" in stored
+
+    def test_add_tags_does_not_duplicate_existing_bucket(self, session: Session):
+        asset = _make_asset(session, "hash-dedupe")
+        ref = _make_reference(session, asset)
+
+        add_tags_to_reference(
+            session, reference_id=ref.id, tags=["models", "checkpoints"]
+        )
+        result = add_tags_to_reference(
+            session, reference_id=ref.id, tags=["checkpoints/flux"]
+        )
+        session.commit()
+
+        # `checkpoints` was already there from the first add; only the
+        # slash-joined token is genuinely new.
+        assert result.added == ["checkpoints/flux"]
+        assert "checkpoints" in result.already_present
+
+    def test_flat_category_is_unaffected(self, session: Session):
+        asset = _make_asset(session, "hash-flat")
+        ref = _make_reference(session, asset)
+
+        result = set_reference_tags(
+            session,
+            reference_id=ref.id,
+            tags=["models", "checkpoints"],
+        )
+        session.commit()
+
+        assert set(result.total) == {"models", "checkpoints"}
+        assert get_reference_tags(session, reference_id=ref.id) == [
+            "models",
+            "checkpoints",
+        ]
+
+    def test_unknown_prefix_passes_through(self, session: Session):
+        asset = _make_asset(session, "hash-user")
+        ref = _make_reference(session, asset)
+
+        # `my-org` isn't a registered bucket — the slash-joined user tag
+        # should not trigger bucket expansion.
+        result = set_reference_tags(
+            session,
+            reference_id=ref.id,
+            tags=["my-org/team-a"],
+        )
+        session.commit()
+
+        assert result.total == ["my-org/team-a"]
+
+
 class TestRemoveTagsFromReference:
     def test_removes_tags(self, session: Session):
         asset = _make_asset(session, "hash1")
diff --git a/tests-unit/assets_test/services/test_bulk_ingest.py b/tests-unit/assets_test/services/test_bulk_ingest.py
index 26e22a01d..4ba6db717 100644
--- a/tests-unit/assets_test/services/test_bulk_ingest.py
+++ b/tests-unit/assets_test/services/test_bulk_ingest.py
@@ -4,7 +4,7 @@ from pathlib import Path
 
 from sqlalchemy.orm import Session
 
-from app.assets.database.models import Asset, AssetReference
+from app.assets.database.models import Asset, AssetReference, AssetReferenceTag
 from app.assets.services.bulk_ingest import SeedAssetSpec, batch_insert_seed_assets
 
 
@@ -102,6 +102,82 @@ class TestBatchInsertSeedAssets:
             assert asset.mime_type == expected_mime, f"Expected {expected_mime} for {filename}, got {asset.mime_type}"
 
 
+class TestBucketPrefixExpansionOnIngest:
+    """Path-scanning ingest must persist the standalone bucket token for
+    nested category paths so the FE set-membership filter
+    (`include_tags=models,checkpoints`) matches assets organized into
+    subfolders (`models/checkpoints/flux/foo.safetensors`).
+    """
+
+    def test_nested_path_inserts_standalone_bucket(
+        self, session: Session, temp_dir: Path
+    ):
+        file_path = temp_dir / "flux.safetensors"
+        file_path.write_bytes(b"content")
+
+        specs: list[SeedAssetSpec] = [
+            {
+                "abs_path": str(file_path),
+                "size_bytes": 7,
+                "mtime_ns": 1234567890000000000,
+                "info_name": "flux",
+                # Shape emitted by get_name_and_tags_from_asset_path for a
+                # nested model path.
+                "tags": ["models", "checkpoints/flux"],
+                "fname": "flux.safetensors",
+                "metadata": None,
+                "hash": None,
+                "mime_type": "application/safetensors",
+            }
+        ]
+
+        result = batch_insert_seed_assets(session, specs=specs, owner_id="")
+
+        assert result.inserted_refs == 1
+        ref = session.query(AssetReference).filter_by(name="flux").one()
+        stored = [
+            row.tag_name
+            for row in session.query(AssetReferenceTag)
+            .filter_by(asset_reference_id=ref.id)
+            .order_by(AssetReferenceTag.added_at.asc())
+            .all()
+        ]
+        assert stored == ["models", "checkpoints/flux", "checkpoints"]
+
+    def test_flat_path_remains_two_tags(
+        self, session: Session, temp_dir: Path
+    ):
+        file_path = temp_dir / "vanilla.safetensors"
+        file_path.write_bytes(b"content")
+
+        specs: list[SeedAssetSpec] = [
+            {
+                "abs_path": str(file_path),
+                "size_bytes": 7,
+                "mtime_ns": 1234567890000000000,
+                "info_name": "vanilla",
+                "tags": ["models", "checkpoints"],
+                "fname": "vanilla.safetensors",
+                "metadata": None,
+                "hash": None,
+                "mime_type": "application/safetensors",
+            }
+        ]
+
+        batch_insert_seed_assets(session, specs=specs, owner_id="")
+
+        ref = session.query(AssetReference).filter_by(name="vanilla").one()
+        stored = {
+            row.tag_name
+            for row in session.query(AssetReferenceTag)
+            .filter_by(asset_reference_id=ref.id)
+            .all()
+        }
+        # Dedupe means flat layouts don't pick up a redundant `checkpoints`
+        # row — tag[1] already serves both positional and set-membership.
+        assert stored == {"models", "checkpoints"}
+
+
 class TestMetadataExtraction:
     def test_extracts_mime_type_for_model_files(self, temp_dir: Path):
         """Verify metadata extraction returns correct mime_type for model files."""
diff --git a/tests-unit/assets_test/test_helpers.py b/tests-unit/assets_test/test_helpers.py
new file mode 100644
index 000000000..c950b726b
--- /dev/null
+++ b/tests-unit/assets_test/test_helpers.py
@@ -0,0 +1,69 @@
+"""Unit tests for app.assets.helpers."""
+
+from app.assets.helpers import expand_bucket_prefixes
+
+
+class TestExpandBucketPrefixes:
+    def test_flat_category_unchanged(self):
+        # `checkpoints` is already a standalone token, no expansion needed.
+        assert expand_bucket_prefixes(["models", "checkpoints"]) == [
+            "models",
+            "checkpoints",
+        ]
+
+    def test_nested_category_inserts_bucket(self):
+        # Path-derived shape for `models/checkpoints/flux/foo.safetensors` —
+        # the standalone bucket has to be present so the FE set-membership
+        # filter (`include_tags=models,checkpoints`) matches the asset.
+        assert expand_bucket_prefixes(["models", "checkpoints/flux"]) == [
+            "models",
+            "checkpoints/flux",
+            "checkpoints",
+        ]
+
+    def test_deeply_nested_only_first_segment_expands(self):
+        # Only the FIRST slash segment ever gets emitted as a standalone —
+        # intermediate path segments don't have routing significance.
+        assert expand_bucket_prefixes(
+            ["models", "diffusers/kolors/text_encoder"]
+        ) == ["models", "diffusers/kolors/text_encoder", "diffusers"]
+
+    def test_unknown_prefix_does_not_expand(self):
+        # Free-form user labels with slashes whose first segment is not a
+        # registered bucket pass through opaquely.
+        assert expand_bucket_prefixes(["models", "my-org/team-a"]) == [
+            "models",
+            "my-org/team-a",
+        ]
+
+    def test_idempotent(self):
+        # Re-applying the helper is a no-op once the bucket is in the set.
+        expanded = expand_bucket_prefixes(["models", "checkpoints/flux"])
+        assert expand_bucket_prefixes(expanded) == expanded
+
+    def test_does_not_duplicate_existing_bucket(self):
+        # If the caller already supplied the standalone bucket, don't add a
+        # second copy.
+        assert expand_bucket_prefixes(
+            ["models", "checkpoints/flux", "checkpoints"]
+        ) == ["models", "checkpoints/flux", "checkpoints"]
+
+    def test_preserves_caller_order(self):
+        # User tags after path tags must stay after; the inserted bucket
+        # token slots in immediately after its slash-joined parent so the
+        # microsecond stagger lands it at path-tier before user-tier.
+        assert expand_bucket_prefixes(
+            ["models", "loras/style", "favorite", "v2"]
+        ) == ["models", "loras/style", "loras", "favorite", "v2"]
+
+    def test_empty_input(self):
+        assert expand_bucket_prefixes([]) == []
+
+    def test_input_root_with_subpath_no_expansion(self):
+        # `portraits` isn't a registered model category, so the input
+        # subpath stays opaque (FE filter doesn't have a checkpoint-loader
+        # analogue for input subfolders).
+        assert expand_bucket_prefixes(["input", "portraits/2026"]) == [
+            "input",
+            "portraits/2026",
+        ]
diff --git a/tests-unit/assets_test/test_user_tag_http_smoke.py b/tests-unit/assets_test/test_user_tag_http_smoke.py
index e12a8b9d0..c461f5a05 100644
--- a/tests-unit/assets_test/test_user_tag_http_smoke.py
+++ b/tests-unit/assets_test/test_user_tag_http_smoke.py
@@ -87,3 +87,49 @@ def test_user_tag_batch_lands_after_path_tags_via_http(
     # Critically: alphabetical sort would put 'aaa-experiment' at position 0.
     assert tags_after.index("aaa-experiment") > tags_after.index("models")
     assert tags_after.index("aaa-experiment") > tags_after.index("checkpoints")
+
+
+@pytest.fixture
+def nested_checkpoint_asset(http: requests.Session, api_base: str):
+    """Upload a checkpoint at the slash-joined path shape cloud emits
+    (`models/checkpoints/flux/...`), then delete it on teardown.
+    """
+    name = "nested_checkpoint.safetensors"
+    tags = ["models", "checkpoints/flux"]
+    files = {"file": (name, b"S" * 4096, "application/octet-stream")}
+    form_data = {
+        "tags": json.dumps(tags),
+        "name": name,
+        "user_metadata": json.dumps({}),
+    }
+    r = http.post(api_base + "/api/assets", files=files, data=form_data, timeout=120)
+    assert r.status_code == 201, r.text
+    body = r.json()
+    yield body
+    http.delete(
+        f"{api_base}/api/assets/{body['id']}?delete_content=true", timeout=30
+    )
+
+
+def test_nested_checkpoint_satisfies_fe_set_filter(
+    http: requests.Session, api_base: str, nested_checkpoint_asset: dict
+):
+    """The case Simon flagged: a nested-path checkpoint must still match
+    `include_tags=models,checkpoints` — the FE combo-widget filter.
+    """
+    ref_id = nested_checkpoint_asset["id"]
+
+    stored = _fetch_asset_tags(http, api_base, ref_id)
+    # tag[1] keeps cloud's slash-joined positional contract; tag[2] holds
+    # the standalone bucket the FE filter looks for.
+    assert stored[:3] == ["models", "checkpoints/flux", "checkpoints"]
+
+    # The actual FE query — exact set-membership across both tokens.
+    r = http.get(
+        f"{api_base}/api/assets",
+        params=[("include_tags", "models"), ("include_tags", "checkpoints")],
+        timeout=30,
+    )
+    assert r.status_code == 200, r.text
+    returned_ids = {a["id"] for a in r.json()["assets"]}
+    assert ref_id in returned_ids