diff --git a/source-intercom-native/source_intercom_native/api.py b/source-intercom-native/source_intercom_native/api.py
index 3afc5f5ee8..925ba308a0 100644
--- a/source-intercom-native/source_intercom_native/api.py
+++ b/source-intercom-native/source_intercom_native/api.py
@@ -263,8 +263,6 @@ async def fetch_tickets(
     url = f"{API}/tickets/search"
     body = _generate_conversations_or_tickets_search_body(start, end)
 
-    count = 0
-
     while True:
         response = TicketsSearchResponse.model_validate_json(
                 await http.request(log, url, "POST", json=body)
@@ -294,7 +292,6 @@ async def fetch_tickets(
 
             if ticket.updated_at > start:
                 yield ticket
-                count += 1
 
         if response.pages.next is None:
             yield _s_to_dt(last_seen_ts)
@@ -318,8 +315,6 @@ async def fetch_conversations(
     url = f"{API}/conversations/search"
     body = _generate_conversations_or_tickets_search_body(start, end)
 
-    count = 0
-
     while True:
         response = ConversationsSearchResponse.model_validate_json(
                 await http.request(log, url, "POST", json=body)
@@ -349,7 +344,6 @@ async def fetch_conversations(
 
             if conversation.updated_at > start:
                 yield conversation
-                count += 1
 
         if response.pages.next is None:
             yield _s_to_dt(last_seen_ts)
@@ -358,6 +352,38 @@ async def fetch_conversations(
         body = _generate_conversations_or_tickets_search_body(start, end, response.pages.next.starting_after)
 
 
+async def _determine_window_end(
+        http: HTTPSession,
+        start: datetime,
+        initial_end: datetime,
+        log: Logger,
+) -> datetime:
+    MAX_PAGE_QUANTITY = 25
+    MIN_WINDOW_SIZE = timedelta(seconds=1)
+    url = f"{API}/conversations/search"
+    end = min(initial_end, datetime.now(tz=UTC))
+
+    while True:
+        body = _generate_conversations_or_tickets_search_body(_dt_to_s(start), _dt_to_s(end))
+        response = ConversationsSearchResponse.model_validate_json(
+                await http.request(log, url, "POST", json=body)
+        )
+
+        total_pages = response.pages.total_pages
+
+        if total_pages <= MAX_PAGE_QUANTITY:
+            return end
+
+        delta = (end - start) / 2
+        # Conversation searches do not have subsecond precision, so we cut off any microseconds from the window size.
+        reduced_window_size = delta - timedelta(microseconds=delta.microseconds)
+
+        if reduced_window_size <= MIN_WINDOW_SIZE:
+            return start + MIN_WINDOW_SIZE
+
+        end = start + reduced_window_size
+
+
 async def fetch_conversations_parts(
     http: HTTPSession,
     window_size: int,
@@ -365,17 +391,28 @@ async def fetch_conversations_parts(
     log_cursor: LogCursor,
 ) -> AsyncGenerator[TimestampedResource | LogCursor, None]:
     assert isinstance(log_cursor, datetime)
+    url = f"{API}/conversations/search"
 
     start = _dt_to_s(log_cursor)
-    max_end = _dt_to_s(log_cursor + timedelta(days=window_size))
-    end = min(max_end, _dt_to_s(datetime.now(tz=UTC)))
+    max_end_dt = log_cursor + timedelta(days=window_size)
+    max_end = _dt_to_s(max_end_dt)
+
+    # Since conversation_parts cannot checkpoint until a complete date window is checked,
+    # _determine_window_end constricts windows to a size that should complete in a reasonable
+    # amount of time.
+    end = _dt_to_s(
+        await _determine_window_end(
+            http=http,
+            start=log_cursor,
+            initial_end=max_end_dt,
+            log=log
+        )
+    )
 
     last_seen_ts = start
 
-    url = f"{API}/conversations/search"
     body = _generate_conversations_or_tickets_search_body(start, end)
 
-    should_log_progress = _is_large_date_window(start, end)
     while True:
         response = ConversationsSearchResponse.model_validate_json(
                 await http.request(log, url, "POST", json=body)
@@ -387,6 +424,8 @@ async def fetch_conversations_parts(
         if total_pages == 0:
             break
 
+        should_log_progress = _is_large_date_window(start, end) or total_pages > 5
+
         if should_log_progress and _is_page_number_to_log(page_num, total_pages):
             log.info(f"Processing page {page_num} of {total_pages}.", {
                 'window_start': _s_to_dt(start),