diff --git a/docs/index.html b/docs/index.html
index 763d65dd..5c1d3466 100644
--- a/docs/index.html
+++ b/docs/index.html
@@ -5,6 +5,15 @@
   <title>Document</title>
   <meta http-equiv="X-UA-Compatible" content="IE=edge,chrome=1" />
   <meta name="description" content="Description">
+
+  <!-- Open Graph metadata -->
+  <meta property="og:title" content="Khoj Documentation">
+  <meta property="og:type" content="website">
+  <meta property="og:site_name" content="Khoj Documentation">
+  <meta property="og:description" content="Quickly get started with using or self-hosting Khoj">
+  <meta property="og:image" content="https://khoj-web-bucket.s3.amazonaws.com/link_preview_docs.png">
+  <meta property="og:url" content="https://docs.khoj.dev">
+
   <meta name="viewport" content="width=device-width, initial-scale=1.0, minimum-scale=1.0">
   <link rel="stylesheet" href="//cdn.jsdelivr.net/npm/docsify/lib/themes/buble.css" />
   <link rel="icon" href="./assets/favicon-128x128.ico">
diff --git a/src/database/migrations/0019_alter_googleuser_family_name_and_more.py b/src/database/migrations/0019_alter_googleuser_family_name_and_more.py
new file mode 100644
index 00000000..bb31adcb
--- /dev/null
+++ b/src/database/migrations/0019_alter_googleuser_family_name_and_more.py
@@ -0,0 +1,27 @@
+# Generated by Django 4.2.7 on 2023-11-19 22:20
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+    dependencies = [
+        ("database", "0018_searchmodelconfig_delete_searchmodel"),
+    ]
+
+    operations = [
+        migrations.AlterField(
+            model_name="googleuser",
+            name="family_name",
+            field=models.CharField(blank=True, default=None, max_length=200, null=True),
+        ),
+        migrations.AlterField(
+            model_name="googleuser",
+            name="given_name",
+            field=models.CharField(blank=True, default=None, max_length=200, null=True),
+        ),
+        migrations.AlterField(
+            model_name="googleuser",
+            name="name",
+            field=models.CharField(blank=True, default=None, max_length=200, null=True),
+        ),
+    ]
diff --git a/src/database/models/__init__.py b/src/database/models/__init__.py
index 92848e5c..92da3e6e 100644
--- a/src/database/models/__init__.py
+++ b/src/database/models/__init__.py
@@ -27,9 +27,9 @@ class GoogleUser(models.Model):
     sub = models.CharField(max_length=200)
     azp = models.CharField(max_length=200)
     email = models.CharField(max_length=200)
-    name = models.CharField(max_length=200)
-    given_name = models.CharField(max_length=200)
-    family_name = models.CharField(max_length=200)
+    name = models.CharField(max_length=200, null=True, default=None, blank=True)
+    given_name = models.CharField(max_length=200, null=True, default=None, blank=True)
+    family_name = models.CharField(max_length=200, null=True, default=None, blank=True)
     picture = models.CharField(max_length=200, null=True, default=None)
     locale = models.CharField(max_length=200)
 
diff --git a/src/khoj/processor/data_sources/org_mode/org_to_entries.py b/src/khoj/processor/data_sources/org_mode/org_to_entries.py
index 0aef9b67..b8d118a7 100644
--- a/src/khoj/processor/data_sources/org_mode/org_to_entries.py
+++ b/src/khoj/processor/data_sources/org_mode/org_to_entries.py
@@ -100,16 +100,17 @@ class OrgToEntries(TextToEntries):
                 continue
 
             todo_str = f"{parsed_entry.todo} " if parsed_entry.todo else ""
-            # Prepend filename as top heading to entry
-            filename = Path(entry_to_file_map[parsed_entry]).stem
+
+            # Prepend ancestor headings, filename as top heading to entry for context
+            ancestors_trail = " / ".join(parsed_entry.ancestors) or Path(entry_to_file_map[parsed_entry])
             if parsed_entry.heading:
-                heading = f"* {filename}\n** {todo_str}{parsed_entry.heading}."
+                heading = f"* Path: {ancestors_trail}\n** {todo_str}{parsed_entry.heading}."
             else:
-                heading = f"* {filename}."
+                heading = f"* Path: {ancestors_trail}."
 
             compiled = heading
             if state.verbose > 2:
-                logger.debug(f"Title: {parsed_entry.heading}")
+                logger.debug(f"Title: {heading}")
 
             if parsed_entry.tags:
                 tags_str = " ".join(parsed_entry.tags)
diff --git a/src/khoj/processor/data_sources/org_mode/orgnode.py b/src/khoj/processor/data_sources/org_mode/orgnode.py
index db660ee7..28f55c17 100644
--- a/src/khoj/processor/data_sources/org_mode/orgnode.py
+++ b/src/khoj/processor/data_sources/org_mode/orgnode.py
@@ -80,6 +80,7 @@ def makelist(file, filename):
     }  # populated from #+SEQ_TODO line
     level = ""
     heading = ""
+    ancestor_headings = []
     bodytext = ""
     introtext = ""
     tags = list()  # set of all tags in headline
@@ -98,7 +99,7 @@ def makelist(file, filename):
         heading_search = re.search(r"^(\*+)\s(.*?)\s*$", line)
         if heading_search:  # we are processing a heading line
             if heading:  # if we have are on second heading, append first heading to headings list
-                thisNode = Orgnode(level, heading, bodytext, tags)
+                thisNode = Orgnode(level, heading, bodytext, tags, ancestor_headings)
                 if closed_date:
                     thisNode.closed = closed_date
                     closed_date = ""
@@ -114,6 +115,8 @@ def makelist(file, filename):
                 thisNode.properties = property_map
                 nodelist.append(thisNode)
             property_map = {"LINE": f"file:{normalize_filename(filename)}::{ctr}"}
+            previous_level = level
+            previous_heading = heading
             level = heading_search.group(1)
             heading = heading_search.group(2)
             bodytext = ""
@@ -126,6 +129,17 @@ def makelist(file, filename):
                     for parsedtag in parsedtags.split(":"):
                         if parsedtag != "":
                             tags.append(parsedtag)
+
+            # Add previous heading to ancestors if current heading is deeper than previous level
+            if len(level) > len(previous_level) and previous_heading:
+                ancestor_headings.append(previous_heading)
+            # Remove last ancestor(s) if current heading is shallower than previous level
+            elif len(level) < len(previous_level):
+                for _ in range(len(level), len(previous_level)):
+                    if not ancestor_headings or len(ancestor_headings) == 0:
+                        break
+                    ancestor_headings.pop()
+
         else:  # we are processing a non-heading line
             if line[:10] == "#+SEQ_TODO":
                 kwlist = re.findall(r"([A-Z]+)\(", line)
@@ -216,7 +230,7 @@ def makelist(file, filename):
         nodelist = [thisNode] + nodelist
     # write out last heading node
     if heading:
-        thisNode = Orgnode(level, heading, bodytext, tags)
+        thisNode = Orgnode(level, heading, bodytext, tags, ancestor_headings)
         thisNode.properties = property_map
         if sched_date:
             thisNode.scheduled = sched_date
@@ -243,6 +257,9 @@ def makelist(file, filename):
             n.priority = priority_search.group(1)
             n.heading = priority_search.group(2)
 
+        # Prefix filepath/title to ancestors
+        n.ancestors = [file_title] + n.ancestors
+
         # Set SOURCE property to a file+heading based org-mode link to the entry
         if n.level == 0:
             n.properties["LINE"] = f"file:{normalize_filename(filename)}::0"
@@ -261,7 +278,7 @@ class Orgnode(object):
     with the headline.
     """
 
-    def __init__(self, level, headline, body, tags):
+    def __init__(self, level, headline, body, tags, ancestor_headings=[]):
         """
         Create an Orgnode object given the parameters of level (as the
         raw asterisks), headline text (including the TODO tag), and
@@ -279,8 +296,21 @@ class Orgnode(object):
         self._closed = ""  # Closed date
         self._properties = dict()
         self._logbook = list()  # List of clock-in, clock-out tuples representing logbook entries
+        self._ancestor_headings = ancestor_headings.copy()
 
-        # Look for priority in headline and transfer to prty field
+    @property
+    def ancestors(self) -> List[str]:
+        """
+        Return the ancestor headings of the node
+        """
+        return self._ancestor_headings
+
+    @ancestors.setter
+    def ancestors(self, new_ancestors):
+        """
+        Update the ancestor headings of the node
+        """
+        self._ancestor_headings = new_ancestors
 
     @property
     def heading(self):
diff --git a/tests/conftest.py b/tests/conftest.py
index d3a27748..669759e5 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -384,6 +384,45 @@ def sample_org_data():
 def get_sample_data(type):
     sample_data = {
         "org": {
+            "elisp.org": """
+* Emacs Khoj
+  /An Emacs interface for [[https://github.com/khoj-ai/khoj][khoj]]/
+
+** Requirements
+   - Install and Run [[https://github.com/khoj-ai/khoj][khoj]]
+
+** Installation
+*** Direct
+     - Put ~khoj.el~ in your Emacs load path. For e.g ~/.emacs.d/lisp
+     - Load via ~use-package~ in your ~/.emacs.d/init.el or .emacs file by adding below snippet
+       #+begin_src elisp
+         ;; Khoj Package
+         (use-package khoj
+           :load-path "~/.emacs.d/lisp/khoj.el"
+           :bind ("C-c s" . 'khoj))
+       #+end_src
+
+*** Using [[https://github.com/quelpa/quelpa#installation][Quelpa]]
+     - Ensure [[https://github.com/quelpa/quelpa#installation][Quelpa]], [[https://github.com/quelpa/quelpa-use-package#installation][quelpa-use-package]] are installed
+     - Add below snippet to your ~/.emacs.d/init.el or .emacs config file and execute it.
+       #+begin_src elisp
+         ;; Khoj Package
+         (use-package khoj
+           :quelpa (khoj :fetcher url :url "https://raw.githubusercontent.com/khoj-ai/khoj/master/interface/emacs/khoj.el")
+           :bind ("C-c s" . 'khoj))
+       #+end_src
+
+** Usage
+   1. Call ~khoj~ using keybinding ~C-c s~ or ~M-x khoj~
+   2. Enter Query in Natural Language
+      e.g "What is the meaning of life?" "What are my life goals?"
+   3. Wait for results
+      *Note: It takes about 15s on a Mac M1 and a ~100K lines corpus of org-mode files*
+   4. (Optional) Narrow down results further
+      Include/Exclude specific words from results by adding to query
+      e.g "What is the meaning of life? -god +none"
+
+""",
             "readme.org": """
 * Khoj
   /Allow natural language search on user content like notes, images using transformer based models/
@@ -399,7 +438,7 @@ def get_sample_data(type):
    git clone https://github.com/khoj-ai/khoj && cd khoj
    conda env create -f environment.yml
    conda activate khoj
-   #+end_src"""
+   #+end_src""",
         },
         "markdown": {
             "readme.markdown": """
diff --git a/tests/data/org/interface_emacs_readme.org b/tests/data/org/interface_emacs_readme.org
index 300f1013..ef43b3cc 100644
--- a/tests/data/org/interface_emacs_readme.org
+++ b/tests/data/org/interface_emacs_readme.org
@@ -4,10 +4,9 @@
 ** Requirements
    - Install and Run [[https://github.com/khoj-ai/khoj][khoj]]
 
-** Installation
-   - Direct Install
+** Install
+*** Direct
      - Put ~khoj.el~ in your Emacs load path. For e.g ~/.emacs.d/lisp
-
      - Load via ~use-package~ in your ~/.emacs.d/init.el or .emacs file by adding below snippet
        #+begin_src elisp
          ;; Khoj Package
@@ -16,7 +15,7 @@
            :bind ("C-c s" . 'khoj))
        #+end_src
 
-   - Use [[https://github.com/quelpa/quelpa#installation][Quelpa]]
+*** Using [[https://github.com/quelpa/quelpa#installation][Quelpa]]
      - Ensure [[https://github.com/quelpa/quelpa#installation][Quelpa]], [[https://github.com/quelpa/quelpa-use-package#installation][quelpa-use-package]] are installed
      - Add below snippet to your ~/.emacs.d/init.el or .emacs config file and execute it.
        #+begin_src elisp
@@ -28,17 +27,10 @@
 
 ** Usage
    1. Call ~khoj~ using keybinding ~C-c s~ or ~M-x khoj~
-
    2. Enter Query in Natural Language
-
       e.g "What is the meaning of life?" "What are my life goals?"
-
    3. Wait for results
-
       *Note: It takes about 15s on a Mac M1 and a ~100K lines corpus of org-mode files*
-
    4. (Optional) Narrow down results further
-
       Include/Exclude specific words from results by adding to query
-
       e.g "What is the meaning of life? -god +none"
diff --git a/tests/data/org/main_readme.org b/tests/data/org/main_readme.org
index 6495d6ba..d88a2b2b 100644
--- a/tests/data/org/main_readme.org
+++ b/tests/data/org/main_readme.org
@@ -22,16 +22,16 @@
    #+end_src
 
 ** Use
-   - *Khoj via Emacs*
+*** *Khoj via Emacs*
      - [[https://github.com/khoj-ai/khoj/tree/master/interface/emacs#installation][Install]] [[./interface/emacs/khoj.el][khoj.el]]
      - Run ~M-x khoj <user-query>~ or Call ~C-c C-s~
 
-   - *Khoj via API*
+*** *Khoj via API*
      - Query: ~GET~ [[http://localhost:42110/api/search?q=%22what%20is%20the%20meaning%20of%20life%22][http://localhost:42110/api/search?q="What is the meaning of life"]]
      - Update Index: ~GET~ [[http://localhost:42110/api/update][http://localhost:42110/api/update]]
      - [[http://localhost:42110/docs][Khoj API Docs]]
 
-   - *Call Khoj via Python Script Directly*
+*** *Call Khoj via Python Script Directly*
      #+begin_src shell
      python3 search_types/asymmetric.py \
      --compressed-jsonl .notes.jsonl.gz \
diff --git a/tests/test_client.py b/tests/test_client.py
index 9c02a05a..52de0c95 100644
--- a/tests/test_client.py
+++ b/tests/test_client.py
@@ -321,7 +321,7 @@ def test_notes_search_with_include_filter(client, sample_org_data, default_user:
     assert response.status_code == 200
     # assert actual_data contains word "Emacs"
     search_result = response.json()[0]["entry"]
-    assert "Emacs" in search_result
+    assert "emacs" in search_result
 
 
 # ----------------------------------------------------------------------------------------------------
@@ -347,6 +347,27 @@ def test_notes_search_with_exclude_filter(client, sample_org_data, default_user:
     assert "clone" not in search_result
 
 
+# ----------------------------------------------------------------------------------------------------
+@pytest.mark.django_db(transaction=True)
+def test_notes_search_requires_parent_context(
+    client, search_config: SearchConfig, sample_org_data, default_user: KhojUser
+):
+    # Arrange
+    headers = {"Authorization": "Bearer kk-secret"}
+    text_search.setup(OrgToEntries, sample_org_data, regenerate=False, user=default_user)
+    user_query = quote("Install Khoj on Emacs")
+
+    # Act
+    response = client.get(f"/api/search?q={user_query}&n=1&t=org&r=true&max_distance=0.18", headers=headers)
+
+    # Assert
+    assert response.status_code == 200
+
+    assert len(response.json()) == 1, "Expected only 1 result"
+    search_result = response.json()[0]["entry"]
+    assert "Emacs load path" in search_result, "Expected 'Emacs load path' in search result"
+
+
 # ----------------------------------------------------------------------------------------------------
 @pytest.mark.django_db(transaction=True)
 def test_different_user_data_not_accessed(client, sample_org_data, default_user: KhojUser):
diff --git a/tests/test_multiple_users.py b/tests/test_multiple_users.py
index 2b1eb2f4..94d0560c 100644
--- a/tests/test_multiple_users.py
+++ b/tests/test_multiple_users.py
@@ -69,7 +69,7 @@ def test_index_update_with_user2_inaccessible_user1(client, api_user2: KhojApiUs
 
     # Assert
     assert update_response.status_code == 200
-    assert len(results) == 4
+    assert len(results) == 5
     for result in results:
         assert result["additional"]["file"] not in source_file_symbol
 
diff --git a/tests/test_org_to_entries.py b/tests/test_org_to_entries.py
index 3b80873a..fb37426a 100644
--- a/tests/test_org_to_entries.py
+++ b/tests/test_org_to_entries.py
@@ -45,9 +45,10 @@ def test_configure_heading_entry_to_jsonl(tmp_path):
             assert is_none_or_empty(jsonl_data)
 
 
-def test_entry_split_when_exceeds_max_words(tmp_path):
+def test_entry_split_when_exceeds_max_words():
     "Ensure entries with compiled words exceeding max_words are split."
     # Arrange
+    tmp_path = "/tmp/test.org"
     entry = f"""*** Heading
     \t\r
     Body Line
@@ -55,7 +56,7 @@ def test_entry_split_when_exceeds_max_words(tmp_path):
     data = {
         f"{tmp_path}": entry,
     }
-    expected_heading = f"* {tmp_path.stem}\n** Heading"
+    expected_heading = f"* Path: {tmp_path}\n** Heading"
 
     # Act
     # Extract Entries from specified Org files
diff --git a/tests/test_orgnode.py b/tests/test_orgnode.py
index 7ee948e2..aa6a3cb9 100644
--- a/tests/test_orgnode.py
+++ b/tests/test_orgnode.py
@@ -161,6 +161,8 @@ Body Line 1"""
     assert len(entries) == 1
     # parsed heading from entry
     assert entries[0].heading == "Heading[1]"
+    # track ancestors of entry
+    assert entries[0].ancestors == [f"{orgfile}"]
     # ensure SOURCE link has square brackets in filename, heading escaped in rendered entries
     escaped_orgfile = f"{orgfile}".replace("[1]", "\\[1\\]")
     assert f":SOURCE: [[file:{escaped_orgfile}::*Heading\\[1\\]" in f"{entries[0]}"
@@ -260,6 +262,7 @@ Body Line 1"""
     assert entries[0].closed == ""
     assert entries[0].scheduled == ""
     assert entries[0].deadline == ""
+    assert entries[0].ancestors == ["test"]
 
 
 # ----------------------------------------------------------------------------------------------------
@@ -284,6 +287,7 @@ Body Line 1
     assert entries[0].closed == ""
     assert entries[0].scheduled == ""
     assert entries[0].deadline == ""
+    assert entries[0].ancestors == ["title1 title2"]
 
 
 # ----------------------------------------------------------------------------------------------------
@@ -304,8 +308,10 @@ entry body
     assert len(entries) == 2
     assert entries[0].heading == "Title"
     assert entries[0].body == "intro body\n"
+    assert entries[0].ancestors == ["Title"]
     assert entries[1].heading == "Entry Heading"
     assert entries[1].body == "entry body\n\n"
+    assert entries[1].ancestors == ["Title"]
 
 
 # ----------------------------------------------------------------------------------------------------
@@ -326,8 +332,93 @@ entry body
     assert len(entries) == 2
     assert entries[0].heading == "Title1 Title2"
     assert entries[0].body == "intro body\n"
+    assert entries[0].ancestors == ["Title1 Title2"]
     assert entries[1].heading == "Entry Heading"
     assert entries[1].body == "entry body\n\n"
+    assert entries[0].ancestors == ["Title1 Title2"]
+
+
+# ----------------------------------------------------------------------------------------------------
+def test_parse_org_with_single_ancestor_heading(tmp_path):
+    "Parse org entries with parent headings context"
+    # Arrange
+    body = f"""
+* Heading 1
+body 1
+** Sub Heading 1
+"""
+    orgfile = create_file(tmp_path, body)
+
+    # Act
+    entries = orgnode.makelist_with_filepath(orgfile)
+
+    # Assert
+    assert len(entries) == 2
+    assert entries[0].heading == "Heading 1"
+    assert entries[0].ancestors == [f"{orgfile}"]
+    assert entries[1].heading == "Sub Heading 1"
+    assert entries[1].ancestors == [f"{orgfile}", "Heading 1"]
+
+
+# ----------------------------------------------------------------------------------------------------
+def test_parse_org_with_multiple_ancestor_headings(tmp_path):
+    "Parse org entries with parent headings context"
+    # Arrange
+    body = f"""
+* Heading 1
+body 1
+** Sub Heading 1
+*** Sub Sub Heading 1
+sub sub body 1
+"""
+    orgfile = create_file(tmp_path, body)
+
+    # Act
+    entries = orgnode.makelist_with_filepath(orgfile)
+
+    # Assert
+    assert len(entries) == 3
+    assert entries[0].heading == "Heading 1"
+    assert entries[0].ancestors == [f"{orgfile}"]
+    assert entries[1].heading == "Sub Heading 1"
+    assert entries[1].ancestors == [f"{orgfile}", "Heading 1"]
+    assert entries[2].heading == "Sub Sub Heading 1"
+    assert entries[2].ancestors == [f"{orgfile}", "Heading 1", "Sub Heading 1"]
+
+
+# ----------------------------------------------------------------------------------------------------
+def test_parse_org_with_multiple_ancestor_headings_of_siblings(tmp_path):
+    "Parse org entries with parent headings context"
+    # Arrange
+    body = f"""
+* Heading 1
+body 1
+** Sub Heading 1
+*** Sub Sub Heading 1
+sub sub body 1
+*** Sub Sub Heading 2
+** Sub Heading 2
+*** Sub Sub Heading 3
+"""
+    orgfile = create_file(tmp_path, body)
+
+    # Act
+    entries = orgnode.makelist_with_filepath(orgfile)
+
+    # Assert
+    assert len(entries) == 6
+    assert entries[0].heading == "Heading 1"
+    assert entries[0].ancestors == [f"{orgfile}"]
+    assert entries[1].heading == "Sub Heading 1"
+    assert entries[1].ancestors == [f"{orgfile}", "Heading 1"]
+    assert entries[2].heading == "Sub Sub Heading 1"
+    assert entries[2].ancestors == [f"{orgfile}", "Heading 1", "Sub Heading 1"]
+    assert entries[3].heading == "Sub Sub Heading 2"
+    assert entries[3].ancestors == [f"{orgfile}", "Heading 1", "Sub Heading 1"]
+    assert entries[4].heading == "Sub Heading 2"
+    assert entries[4].ancestors == [f"{orgfile}", "Heading 1"]
+    assert entries[5].heading == "Sub Sub Heading 3"
+    assert entries[5].ancestors == [f"{orgfile}", "Heading 1", "Sub Heading 2"]
 
 
 # Helper Functions
diff --git a/tests/test_text_search.py b/tests/test_text_search.py
index ac24c9a0..4d08d5e8 100644
--- a/tests/test_text_search.py
+++ b/tests/test_text_search.py
@@ -70,7 +70,7 @@ def test_text_search_setup_with_empty_file_creates_no_entries(
         text_search.setup(OrgToEntries, data, regenerate=True, user=default_user)
 
     # Assert
-    assert "Deleted 3 entries. Created 0 new entries for user " in caplog.records[-1].message
+    assert "Deleted 8 entries. Created 0 new entries for user " in caplog.records[-1].message
     verify_embeddings(0, default_user)
 
 
@@ -90,7 +90,7 @@ def test_text_indexer_deletes_embedding_before_regenerate(
 
     # Assert
     assert "Deleting all entries for file type org" in caplog.text
-    assert "Deleted 3 entries. Created 10 new entries for user " in caplog.records[-1].message
+    assert "Deleted 8 entries. Created 13 new entries for user " in caplog.records[-1].message
 
 
 # ----------------------------------------------------------------------------------------------------
@@ -106,7 +106,7 @@ def test_text_search_setup_batch_processes(content_config: ContentConfig, defaul
         text_search.setup(OrgToEntries, data, regenerate=True, user=default_user)
 
     # Assert
-    assert "Deleted 3 entries. Created 10 new entries for user " in caplog.records[-1].message
+    assert "Deleted 8 entries. Created 13 new entries for user " in caplog.records[-1].message
 
 
 # ----------------------------------------------------------------------------------------------------
@@ -161,7 +161,7 @@ async def test_text_search(search_config: SearchConfig):
         default_user,
     )
 
-    query = "How to git install application?"
+    query = "Load Khoj on Emacs?"
 
     # Act
     hits = await text_search.query(default_user, query)
@@ -170,7 +170,7 @@ async def test_text_search(search_config: SearchConfig):
 
     # Assert
     search_result = results[0].entry
-    assert "git clone" in search_result, 'search result did not contain "git clone" entry'
+    assert "Emacs load path" in search_result, 'Expected "Emacs load path" in entry'
 
 
 # ----------------------------------------------------------------------------------------------------
@@ -284,9 +284,9 @@ def test_regenerate_index_with_new_entry(
     final_logs = caplog.text
 
     # Assert
-    assert "Deleted 3 entries. Created 10 new entries for user " in initial_logs
-    assert "Deleted 10 entries. Created 11 new entries for user " in final_logs
-    verify_embeddings(11, default_user)
+    assert "Deleted 8 entries. Created 13 new entries for user " in initial_logs
+    assert "Deleted 13 entries. Created 14 new entries for user " in final_logs
+    verify_embeddings(14, default_user)
 
 
 # ----------------------------------------------------------------------------------------------------
@@ -320,7 +320,7 @@ def test_update_index_with_duplicate_entries_in_stable_order(
 
     # Assert
     # verify only 1 entry added even if there are multiple duplicate entries
-    assert "Deleted 3 entries. Created 1 new entries for user " in initial_logs
+    assert "Deleted 8 entries. Created 1 new entries for user " in initial_logs
     assert "Deleted 0 entries. Created 0 new entries for user " in final_logs
 
     verify_embeddings(1, default_user)
@@ -357,7 +357,7 @@ def test_update_index_with_deleted_entry(org_config_with_only_new_file: LocalOrg
 
     # Assert
     # verify only 1 entry added even if there are multiple duplicate entries
-    assert "Deleted 3 entries. Created 2 new entries for user " in initial_logs
+    assert "Deleted 8 entries. Created 2 new entries for user " in initial_logs
     assert "Deleted 1 entries. Created 0 new entries for user " in final_logs
 
     verify_embeddings(1, default_user)
@@ -388,9 +388,9 @@ def test_update_index_with_new_entry(content_config: ContentConfig, new_org_file
     final_logs = caplog.text
 
     # Assert
-    assert "Deleted 3 entries. Created 10 new entries for user " in initial_logs
+    assert "Deleted 8 entries. Created 13 new entries for user " in initial_logs
     assert "Deleted 0 entries. Created 1 new entries for user " in final_logs
-    verify_embeddings(11, default_user)
+    verify_embeddings(14, default_user)
 
 
 # ----------------------------------------------------------------------------------------------------
diff --git a/tests/test_word_filter.py b/tests/test_word_filter.py
index 2ede35e7..ebd6cccf 100644
--- a/tests/test_word_filter.py
+++ b/tests/test_word_filter.py
@@ -3,6 +3,25 @@ from khoj.search_filter.word_filter import WordFilter
 from khoj.utils.rawconfig import Entry
 
 
+# Test
+# ----------------------------------------------------------------------------------------------------
+def test_no_word_filter():
+    # Arrange
+    word_filter = WordFilter()
+    q_with_no_filter = "head tail"
+
+    # Act
+    can_filter = word_filter.can_filter(q_with_no_filter)
+    filter_terms = word_filter.get_filter_terms(q_with_no_filter)
+
+    # Assert
+    assert can_filter == False
+    assert filter_terms == []
+
+
+# ----------------------------------------------------------------------------------------------------
+
+
 def test_word_exclude_filter():
     # Arrange
     word_filter = WordFilter()
@@ -15,6 +34,7 @@ def test_word_exclude_filter():
     assert can_filter == True
 
 
+# ----------------------------------------------------------------------------------------------------
 def test_word_include_filter():
     # Arrange
     word_filter = WordFilter()
@@ -27,6 +47,7 @@ def test_word_include_filter():
     assert can_filter == True
 
 
+# ----------------------------------------------------------------------------------------------------
 def test_word_include_and_exclude_filter():
     # Arrange
     word_filter = WordFilter()
@@ -39,6 +60,7 @@ def test_word_include_and_exclude_filter():
     assert can_filter == True
 
 
+# ----------------------------------------------------------------------------------------------------
 def test_get_word_filter_terms():
     # Arrange
     word_filter = WordFilter()