diff --git a/backend/onyx/connectors/confluence/connector.py b/backend/onyx/connectors/confluence/connector.py
index 4407fdd557d..de220b890f2 100644
--- a/backend/onyx/connectors/confluence/connector.py
+++ b/backend/onyx/connectors/confluence/connector.py
@@ -265,6 +265,7 @@ def _convert_page_to_document(
             # Extract basic page information
             page_id = page["id"]
             page_title = page["title"]
+            logger.info(f"Converting page {page_title} to document")
             page_url = build_confluence_document_id(
                 self.wiki_base, page["_links"]["webui"], self.is_cloud
             )
@@ -396,7 +397,9 @@ def _fetch_page_attachments(
                 )
                 continue
 
-            logger.info(f"Processing attachment: {attachment['title']}")
+            logger.info(
+                f"Processing attachment: {attachment['title']} attached to page {page['title']}"
+            )
 
             # Attempt to get textual content or image summarization:
             object_url = build_confluence_document_id(
@@ -458,7 +461,9 @@ def _fetch_document_batches(
              - Attempt to convert it with convert_attachment_to_content(...)
              - If successful, create a new Section with the extracted text or summary.
         """
-        doc_count = 0
+
+        # number of documents/errors yielded
+        yield_count = 0
 
         checkpoint = copy.deepcopy(checkpoint)
         prev_doc_ids = checkpoint.last_seen_doc_ids
@@ -474,12 +479,17 @@ def _fetch_document_batches(
             expand=",".join(_PAGE_EXPANSION_FIELDS),
             limit=2 * self.batch_size,
         ):
+            # create checkpoint after enough documents have been processed
+            if yield_count >= self.batch_size:
+                return checkpoint
+
             if page["id"] in prev_doc_ids:
                 # There are a few seconds of fuzziness in the request,
                 # so we skip if we saw this page on the last run
                 continue
             # Build doc from page
             doc_or_failure = self._convert_page_to_document(page)
+            yield_count += 1
 
             if isinstance(doc_or_failure, ConnectorFailure):
                 yield doc_or_failure
@@ -497,14 +507,10 @@ def _fetch_document_batches(
                 continue
 
             # yield completed document
-            doc_count += 1
+
             checkpoint.last_seen_doc_ids.append(page["id"])
             yield doc_or_failure
 
-            # create checkpoint after enough documents have been processed
-            if doc_count >= self.batch_size:
-                return checkpoint
-
         checkpoint.has_more = False
         return checkpoint
 
diff --git a/backend/tests/unit/onyx/connectors/confluence/test_confluence_checkpointing.py b/backend/tests/unit/onyx/connectors/confluence/test_confluence_checkpointing.py
index 30f4e041938..c5fc5d19d97 100644
--- a/backend/tests/unit/onyx/connectors/confluence/test_confluence_checkpointing.py
+++ b/backend/tests/unit/onyx/connectors/confluence/test_confluence_checkpointing.py
@@ -148,7 +148,7 @@ def test_load_from_checkpoint_happy_path(
     assert confluence_client is not None, "bad test setup"
     paginated_cql_mock = cast(MagicMock, confluence_client.paginated_cql_retrieval)
     paginated_cql_mock.side_effect = [
-        [mock_page1, mock_page2],
+        [mock_page1, mock_page2, mock_page3],
         [],  # comments
         [],  # attachments
         [],  # comments
@@ -366,22 +366,16 @@ def test_checkpoint_progress(
         confluence_connector, 0, end_time
     )
 
-    assert len(outputs) == 2
+    assert len(outputs) == 1
 
     first_checkpoint = outputs[0].next_checkpoint
-    last_checkpoint = outputs[-1].next_checkpoint
 
     assert first_checkpoint == ConfluenceCheckpoint(
         last_updated=later_timestamp.timestamp(),
-        has_more=True,
+        has_more=False,
         last_seen_doc_ids=["1", "2"],
     )
 
-    # Verify checkpoint contains both document IDs and latest timestamp
-    assert last_checkpoint == ConfluenceCheckpoint(
-        last_updated=later_timestamp.timestamp(), has_more=False, last_seen_doc_ids=[]
-    )
-
     assert len(outputs[0].items) == 2
     assert isinstance(outputs[0].items[0], Document)
     assert outputs[0].items[0].semantic_identifier == "Page 1"
@@ -404,11 +398,12 @@ def test_checkpoint_progress(
     ]
 
     # Use the checkpoint from first run
+    first_checkpoint.has_more = True
     outputs_with_checkpoint = load_everything_from_checkpoint_connector_from_checkpoint(
         confluence_connector, 0, end_time, first_checkpoint
     )
 
-    # Verify no documents were processed since they were in last_seen_doc_ids
+    # Verify only the new page was processed since the others were in last_seen_doc_ids
     assert len(outputs_with_checkpoint) == 1
     assert len(outputs_with_checkpoint[0].items) == 1
     assert isinstance(outputs_with_checkpoint[0].items[0], Document)