diff --git a/surfsense_backend/app/schemas/obsidian_plugin.py b/surfsense_backend/app/schemas/obsidian_plugin.py
index 745886ef6..1b3ea7971 100644
--- a/surfsense_backend/app/schemas/obsidian_plugin.py
+++ b/surfsense_backend/app/schemas/obsidian_plugin.py
@@ -21,6 +21,13 @@ class _PluginBase(BaseModel):
     model_config = _PLUGIN_MODEL_CONFIG
 
 
+class HeadingRef(_PluginBase):
+    """One markdown heading extracted from Obsidian metadata cache."""
+
+    heading: str
+    level: int = Field(ge=1, le=6)
+
+
 class NotePayload(_PluginBase):
     """One Obsidian note as pushed by the plugin (the source of truth)."""
 
@@ -36,7 +43,7 @@ class NotePayload(_PluginBase):
 
     frontmatter: dict[str, Any] = Field(default_factory=dict)
     tags: list[str] = Field(default_factory=list)
-    headings: list[str] = Field(default_factory=list)
+    headings: list[HeadingRef] = Field(default_factory=list)
     resolved_links: list[str] = Field(default_factory=list)
     unresolved_links: list[str] = Field(default_factory=list)
     embeds: list[str] = Field(default_factory=list)
diff --git a/surfsense_backend/app/services/obsidian_plugin_indexer.py b/surfsense_backend/app/services/obsidian_plugin_indexer.py
index 5afdbf886..5b037a098 100644
--- a/surfsense_backend/app/services/obsidian_plugin_indexer.py
+++ b/surfsense_backend/app/services/obsidian_plugin_indexer.py
@@ -53,7 +53,6 @@ from app.schemas.obsidian_plugin import (
     ManifestResponse,
     NotePayload,
 )
-from app.services.llm_service import get_user_long_context_llm
 from app.utils.document_converters import generate_unique_identifier_hash
 from app.utils.document_versioning import create_version_snapshot
 
@@ -102,7 +101,7 @@ def _build_metadata(
         "extension": payload.extension,
         "frontmatter": payload.frontmatter,
         "tags": payload.tags,
-        "headings": payload.headings,
+        "headings": [h.model_dump() for h in payload.headings],
         "outgoing_links": payload.resolved_links,
         "unresolved_links": payload.unresolved_links,
         "embeds": payload.embeds,
@@ -237,6 +236,8 @@ async def upsert_note(
 
     document = prepared[0]
 
+    from app.services.llm_service import get_user_long_context_llm
+
     llm = await get_user_long_context_llm(session, str(user_id), search_space_id)
     return await pipeline.index(document, connector_doc, llm)
 
diff --git a/surfsense_backend/tests/integration/test_obsidian_plugin_routes.py b/surfsense_backend/tests/integration/test_obsidian_plugin_routes.py
index 1dd7e2a23..d1e94c1c5 100644
--- a/surfsense_backend/tests/integration/test_obsidian_plugin_routes.py
+++ b/surfsense_backend/tests/integration/test_obsidian_plugin_routes.py
@@ -46,6 +46,7 @@ from app.schemas.obsidian_plugin import (
     ConnectRequest,
     DeleteAck,
     DeleteBatchRequest,
+    HeadingRef,
     ManifestResponse,
     NotePayload,
     RenameAck,
@@ -74,6 +75,7 @@ def _make_note_payload(vault_id: str, path: str, content_hash: str) -> NotePaylo
         name=path.rsplit("/", 1)[-1].rsplit(".", 1)[0],
         extension="md",
         content="# Test\n\nbody",
+        headings=[HeadingRef(heading="Test", level=1)],
         content_hash=content_hash,
         mtime=now,
         ctime=now,
diff --git a/surfsense_backend/tests/unit/test_obsidian_plugin_indexer.py b/surfsense_backend/tests/unit/test_obsidian_plugin_indexer.py
new file mode 100644
index 000000000..a557ea208
--- /dev/null
+++ b/surfsense_backend/tests/unit/test_obsidian_plugin_indexer.py
@@ -0,0 +1,25 @@
+from __future__ import annotations
+
+from datetime import UTC, datetime
+
+from app.schemas.obsidian_plugin import HeadingRef, NotePayload
+from app.services.obsidian_plugin_indexer import _build_metadata
+
+
+def test_build_metadata_serializes_headings_to_plain_json() -> None:
+    now = datetime.now(UTC)
+    payload = NotePayload(
+        vault_id="vault-1",
+        path="notes.md",
+        name="notes",
+        extension="md",
+        content="# Notes",
+        headings=[HeadingRef(heading="Notes", level=1)],
+        content_hash="abc123",
+        mtime=now,
+        ctime=now,
+    )
+
+    metadata = _build_metadata(payload, vault_name="My Vault", connector_id=42)
+
+    assert metadata["headings"] == [{"heading": "Notes", "level": 1}]