diff --git a/src/documents/tests/test_document_model.py b/src/documents/tests/test_document_model.py
index 57486a757..8a58f4b13 100644
--- a/src/documents/tests/test_document_model.py
+++ b/src/documents/tests/test_document_model.py
@@ -156,6 +156,46 @@ class TestDocument(TestCase):
         )
         self.assertEqual(doc.get_public_filename(), "2020-12-25 test")
 
+    def test_suggestion_content_uses_latest_version_content_for_root_documents(
+        self,
+    ) -> None:
+        root = Document.objects.create(
+            title="root",
+            checksum="root",
+            mime_type="application/pdf",
+            content="outdated root content",
+        )
+        version = Document.objects.create(
+            title="v1",
+            checksum="v1",
+            mime_type="application/pdf",
+            root_document=root,
+            content="latest version content",
+        )
+
+        self.assertEqual(root.suggestion_content, version.content)
+
+    def test_content_length_is_per_document_row_for_versions(self) -> None:
+        root = Document.objects.create(
+            title="root",
+            checksum="root",
+            mime_type="application/pdf",
+            content="abc",
+        )
+        version = Document.objects.create(
+            title="v1",
+            checksum="v1",
+            mime_type="application/pdf",
+            root_document=root,
+            content="abcdefgh",
+        )
+
+        root.refresh_from_db()
+        version.refresh_from_db()
+
+        self.assertEqual(root.content_length, 3)
+        self.assertEqual(version.content_length, 8)
+
 
 def test_suggestion_content() -> None:
     """
diff --git a/src/documents/tests/test_matchables.py b/src/documents/tests/test_matchables.py
index 04ff3f6d3..e038bf786 100644
--- a/src/documents/tests/test_matchables.py
+++ b/src/documents/tests/test_matchables.py
@@ -48,6 +48,52 @@ class _TestMatchingBase(TestCase):
 
 
 class TestMatching(_TestMatchingBase):
+    def test_matches_uses_latest_version_content_for_root_documents(self) -> None:
+        root = Document.objects.create(
+            title="root",
+            checksum="root",
+            mime_type="application/pdf",
+            content="root content without token",
+        )
+        Document.objects.create(
+            title="v1",
+            checksum="v1",
+            mime_type="application/pdf",
+            root_document=root,
+            content="latest version contains keyword",
+        )
+        tag = Tag.objects.create(
+            name="tag",
+            match="keyword",
+            matching_algorithm=Tag.MATCH_ANY,
+        )
+
+        self.assertTrue(matching.matches(tag, root))
+
+    def test_matches_does_not_fall_back_to_root_content_when_version_exists(
+        self,
+    ) -> None:
+        root = Document.objects.create(
+            title="root",
+            checksum="root",
+            mime_type="application/pdf",
+            content="root contains keyword",
+        )
+        Document.objects.create(
+            title="v1",
+            checksum="v1",
+            mime_type="application/pdf",
+            root_document=root,
+            content="latest version without token",
+        )
+        tag = Tag.objects.create(
+            name="tag",
+            match="keyword",
+            matching_algorithm=Tag.MATCH_ANY,
+        )
+
+        self.assertFalse(matching.matches(tag, root))
+
     def test_match_none(self) -> None:
         self._test_matching(
             "",