diff --git a/conf/init/runmigration.sh b/conf/init/runmigration.sh
index 5a2ef5cae..a82349dcf 100755
--- a/conf/init/runmigration.sh
+++ b/conf/init/runmigration.sh
@@ -3,3 +3,6 @@ set -e
 
 # Run the database migration
 PYTHONPATH=. venv/bin/alembic upgrade head
+
+# Run the uncompressed size migration
+PYTHONPATH=. venv/bin/python -m util.uncompressedsize
\ No newline at end of file
diff --git a/data/migrations/versions/2430f55c41d5_calculate_uncompressed_sizes_for_all_.py b/data/migrations/versions/2430f55c41d5_calculate_uncompressed_sizes_for_all_.py
index df2ed6f14..03f6d7733 100644
--- a/data/migrations/versions/2430f55c41d5_calculate_uncompressed_sizes_for_all_.py
+++ b/data/migrations/versions/2430f55c41d5_calculate_uncompressed_sizes_for_all_.py
@@ -16,7 +16,9 @@ from util.uncompressedsize import backfill_sizes_from_data
 
 
 def upgrade(tables):
-  backfill_sizes_from_data()
+  # Note: Doing non-alembic operations inside alembic can cause a deadlock. This call has been
+  # moved to runmigration.sh.
+  pass
 
 def downgrade(tables):
   pass
diff --git a/util/uncompressedsize.py b/util/uncompressedsize.py
index 771a06abf..712d33fff 100644
--- a/util/uncompressedsize.py
+++ b/util/uncompressedsize.py
@@ -15,28 +15,29 @@ logger = logging.getLogger(__name__)
 CHUNK_SIZE = 5 * 1024 * 1024
 
 def backfill_sizes_from_data():
-  logger.setLevel(logging.DEBUG)
-  logger.debug('Starting uncompressed image size backfill')
+  logger.setLevel(logging.DEBUG)  
+
+  logger.debug('Starting uncompressed image size backfill with DBURI: %s', app.config['DB_URI'])
+  logger.debug('NOTE: This can be a LONG RUNNING OPERATION. Please wait!')
 
   # Make sure we have a reference to the current DB.
   configure(app.config)
 
-  formatter = logging.Formatter('%(asctime)s - %(name)s - %(levelname)s - %(message)s')
-  
-  ch = logging.StreamHandler(sys.stdout)
-  ch.setFormatter(formatter)
-  logger.addHandler(ch)
+  logger.debug('Uncompressed backfill: Database configured')
 
-  encountered = set()
+  # Check for any uncompressed images.
+  has_images = bool(list(ImageStorage
+                         .select(ImageStorage.uuid)
+                         .where(ImageStorage.uncompressed_size >> None,
+                                ImageStorage.uploading == False)
+                         .limit(1)))
 
-  # Try reading the ImageStorage table count. If it doesn't exist, then this is a postgres
-  # initial setup migration and we can skip this step anyway.
-  try:
-    ImageStorage.select().count()
-  except:
-    logger.debug('Skipping migration for new setup')
+  if not has_images:
+    logger.debug('Uncompressed backfill: No migration needed')
     return
 
+  logger.debug('Uncompressed backfill: Starting migration')
+  encountered = set()
   while True:
     # Load the record from the DB.
     batch_ids = list(ImageStorage
@@ -46,15 +47,19 @@ def backfill_sizes_from_data():
                      .limit(100)
                      .order_by(db_random_func()))
 
-    batch_ids = set(batch_ids) - encountered
+    batch_ids = set([s.uuid for s in batch_ids]) - encountered
+    logger.debug('Found %s images to process', len(batch_ids))
     if len(batch_ids) == 0:
       # We're done!
       return
 
-    for record in batch_ids:
-      uuid = record.uuid
+    counter = 1
+    for uuid in batch_ids:
       encountered.add(uuid)
 
+      logger.debug('Processing image ID %s (%s/%s)', uuid, counter, len(batch_ids))
+      counter = counter + 1
+
       try:
         with_locs = model.get_storage_by_uuid(uuid)
         if with_locs.uncompressed_size is not None: