diff --git a/mergin/client_push.py b/mergin/client_push.py
index 715258e0..31a64d7a 100644
--- a/mergin/client_push.py
+++ b/mergin/client_push.py
@@ -133,10 +133,6 @@ def push_project_async(mc, directory):
     total_size = 0
     # prepare file chunks for upload
     for file in upload_files:
-        # do checkpoint to push changes from wal file to gpkg if there is no diff
-        if "diff" not in file and mp.is_versioned_file(file["path"]):
-            do_sqlite_checkpoint(mp.fpath(file["path"]))
-            file["checksum"] = generate_checksum(mp.fpath(file["path"]))
         file['location'] = mp.fpath_meta(file['diff']['path']) if 'diff' in file else mp.fpath(file['path'])
 
         for chunk_index, chunk_id in enumerate(file["chunks"]):
@@ -210,16 +206,17 @@ def push_project_finalize(job):
             resp = job.mc.post("/v1/project/push/finish/%s" % job.transaction_id)
             job.server_resp = json.load(resp)
         except ClientError as err:
-            job.mc.post("/v1/project/push/cancel/%s" % job.transaction_id)
             # server returns various error messages with filename or something generic
             # it would be better if it returned list of failed files (and reasons) whenever possible
-            return {'error': str(err)}
-
-    if 'error' in job.server_resp:
-        #TODO would be good to get some detailed info from server so user could decide what to do with it
-        # e.g. diff conflicts, basefiles issues, or any other failure
-        job.mp.log.error("push failed. server response: " + job.server_resp['error'])
-        raise ClientError(job.server_resp['error'])
+            job.mp.log.error("--- push finish failed! " + str(err))
+
+            # if push finish fails, the transaction is not killed, so we
+            # need to cancel it so it does not block further uploads
+            job.mp.log.info("canceling the pending transaction...")
+            resp_cancel = job.mc.post("/v1/project/push/cancel/%s" % job.transaction_id)
+            server_resp_cancel = json.load(resp_cancel)
+            job.mp.log.info("cancel response: " + str(server_resp_cancel))
+            raise err
 
     job.mp.metadata = {
         'name': job.project_path,
diff --git a/mergin/merginproject.py b/mergin/merginproject.py
index 1a02de51..cc3126a8 100644
--- a/mergin/merginproject.py
+++ b/mergin/merginproject.py
@@ -289,7 +289,7 @@ def get_push_changes(self):
         changes = self.compare_file_sets(self.metadata['files'], self.inspect_files())
         # do checkpoint to push changes from wal file to gpkg
         for file in changes['added'] + changes['updated']:
-            size, checksum = do_sqlite_checkpoint(self.fpath(file["path"]))
+            size, checksum = do_sqlite_checkpoint(self.fpath(file["path"]), self.log)
             if size and checksum:
                 file["size"] = size
                 file["checksum"] = checksum
diff --git a/mergin/utils.py b/mergin/utils.py
index f7944e66..84045052 100644
--- a/mergin/utils.py
+++ b/mergin/utils.py
@@ -69,25 +69,33 @@ def int_version(version):
     return int(version.lstrip('v')) if re.match(r'v\d', version) else None
 
 
-def do_sqlite_checkpoint(path):
+def do_sqlite_checkpoint(path, log=None):
     """
     Function to do checkpoint over the geopackage file which was not able to do diff file.
 
     :param path: file's absolute path on disk
     :type path: str
+    :param log: optional reference to a logger
+    :type log: logging.Logger
     :returns: new size and checksum of file after checkpoint
     :rtype: int, str
     """
     new_size = None
     new_checksum = None
     if ".gpkg" in path and os.path.exists(f'{path}-wal'):
+        if log:
+            log.info("checkpoint - going to add it in " + path)
         conn = sqlite3.connect(path)
         cursor = conn.cursor()
         cursor.execute("PRAGMA wal_checkpoint=FULL")
+        if log:
+            log.info("checkpoint - return value: " + str(cursor.fetchone()))
         cursor.execute("VACUUM")
         conn.commit()
         conn.close()
         new_size = os.path.getsize(path)
         new_checksum = generate_checksum(path)
+        if log:
+            log.info("checkpoint - new size {} checksum {}".format(new_size, new_checksum))
 
     return new_size, new_checksum