diff --git a/data/database.py b/data/database.py
index 297656c6c..b4d7ba986 100644
--- a/data/database.py
+++ b/data/database.py
@@ -784,6 +784,8 @@ class BlobUpload(BaseModel):
   sha_state = ResumableSHAField(null=True, default=resumablehashlib.sha256)
   location = ForeignKeyField(ImageStorageLocation)
   storage_metadata = JSONField(null=True, default={})
+  chunk_count = IntegerField(default=0)
+  uncompressed_byte_count = IntegerField(null=True)
 
   class Meta:
     database = db
diff --git a/data/migrations/versions/403d02fea323_add_new_blobupload_columns.py b/data/migrations/versions/403d02fea323_add_new_blobupload_columns.py
new file mode 100644
index 000000000..cb5b74317
--- /dev/null
+++ b/data/migrations/versions/403d02fea323_add_new_blobupload_columns.py
@@ -0,0 +1,28 @@
+"""Add new blobupload columns
+
+Revision ID: 403d02fea323
+Revises: 10b999e8db1f
+Create Date: 2015-11-30 14:25:46.822730
+
+"""
+
+# revision identifiers, used by Alembic.
+revision = '403d02fea323'
+down_revision = '10b999e8db1f'
+
+from alembic import op
+import sqlalchemy as sa
+from sqlalchemy.dialects import mysql
+
+def upgrade(tables):
+    ### commands auto generated by Alembic - please adjust! ###
+    op.add_column('blobupload', sa.Column('chunk_count', sa.Integer(), nullable=False))
+    op.add_column('blobupload', sa.Column('uncompressed_byte_count', sa.Integer(), nullable=True))
+    ### end Alembic commands ###
+
+
+def downgrade(tables):
+    ### commands auto generated by Alembic - please adjust! ###
+    op.drop_column('blobupload', 'uncompressed_byte_count')
+    op.drop_column('blobupload', 'chunk_count')
+    ### end Alembic commands ###
diff --git a/data/model/blob.py b/data/model/blob.py
index b05ce6100..263978ec1 100644
--- a/data/model/blob.py
+++ b/data/model/blob.py
@@ -26,7 +26,7 @@ def get_repo_blob_by_digest(namespace, repo_name, blob_digest):
 
 
 def store_blob_record_and_temp_link(namespace, repo_name, blob_digest, location_obj, byte_count,
-                                    link_expiration_s):
+                                    link_expiration_s, uncompressed_byte_count=None):
   """ Store a record of the blob and temporarily link it to the specified repository.
   """
   random_image_name = str(uuid4())
@@ -35,6 +35,7 @@ def store_blob_record_and_temp_link(namespace, repo_name, blob_digest, location_
     try:
       storage = ImageStorage.get(content_checksum=blob_digest)
       storage.image_size = byte_count
+      storage.uncompressed_size = uncompressed_byte_count
       storage.save()
 
       ImageStoragePlacement.get(storage=storage, location=location_obj)
diff --git a/endpoints/v2/blob.py b/endpoints/v2/blob.py
index e7525c8a9..0d8dc4a4e 100644
--- a/endpoints/v2/blob.py
+++ b/endpoints/v2/blob.py
@@ -13,6 +13,7 @@ from auth.jwt_auth import process_jwt_auth
 from endpoints.decorators import anon_protect
 from util.cache import cache_control
 from util.registry.filelike import wrap_with_handler, StreamSlice
+from util.registry.gzipstream import calculate_size_handler
 from storage.basestorage import InvalidChunkException
 
 
@@ -220,6 +221,14 @@ def _upload_chunk(namespace, repo_name, upload_uuid):
 
     input_fp = wrap_with_handler(input_fp, found.sha_state.update)
 
+    # If this is the first chunk and we're starting at the 0 offset, add a handler to gunzip the
+    # stream so we can determine the uncompressed size. We'll throw out this data if another chunk
+    # comes in, but in the common case Docker only sends one chunk.
+    size_info = None
+    if start_offset == 0 and found.chunk_count == 0:
+      size_info, fn = calculate_size_handler()
+      input_fp = wrap_with_handler(input_fp, fn)
+
     try:
       length_written, new_metadata, error = storage.stream_upload_chunk(location_set, upload_uuid,
                                                                         start_offset, length, input_fp,
@@ -228,8 +237,18 @@ def _upload_chunk(namespace, repo_name, upload_uuid):
     except InvalidChunkException:
       _range_not_satisfiable(found.byte_count)
 
+  # If we determined an uncompressed size and this is the first chunk, add it to the blob.
+  # Otherwise, we clear the size from the blob as it was uploaded in multiple chunks.
+  if size_info is not None and found.chunk_count == 0 and size_info.is_valid:
+    found.uncompressed_byte_count = size_info.uncompressed_size
+  elif length_written > 0:
+    # Otherwise, if we wrote some bytes and the above conditions were not met, then we don't
+    # know the uncompressed size.
+    found.uncompressed_byte_count = None
+
   found.storage_metadata = new_metadata
   found.byte_count += length_written
+  found.chunk_count += 1
   return found, error
 
 
@@ -257,7 +276,8 @@ def _finish_upload(namespace, repo_name, upload_obj, expected_digest):
   # Mark the blob as uploaded.
   model.blob.store_blob_record_and_temp_link(namespace, repo_name, expected_digest,
                                              upload_obj.location, upload_obj.byte_count,
-                                             app.config['PUSH_TEMP_TAG_EXPIRATION_SEC'])
+                                             app.config['PUSH_TEMP_TAG_EXPIRATION_SEC'],
+                                             upload_obj.uncompressed_byte_count)
 
   # Delete the upload tracking row.
   upload_obj.delete_instance()
diff --git a/test/data/test.db b/test/data/test.db
index 335b28e34..09d116ec4 100644
Binary files a/test/data/test.db and b/test/data/test.db differ
diff --git a/util/registry/gzipstream.py b/util/registry/gzipstream.py
index 0f9ce1e6b..3a3f28542 100644
--- a/util/registry/gzipstream.py
+++ b/util/registry/gzipstream.py
@@ -16,6 +16,7 @@ class SizeInfo(object):
   def __init__(self):
     self.uncompressed_size = 0
     self.compressed_size = 0
+    self.is_valid = True
 
 def calculate_size_handler():
   """ Returns an object and a SocketReader handler. The handler will gunzip the data it receives,
@@ -23,17 +24,26 @@ def calculate_size_handler():
   """
 
   size_info = SizeInfo()
-
   decompressor = zlib.decompressobj(ZLIB_GZIP_WINDOW)
 
   def fn(buf):
+    if not size_info.is_valid:
+      return
+
     # Note: We set a maximum CHUNK_SIZE to prevent the decompress from taking too much
     # memory. As a result, we have to loop until the unconsumed tail is empty.
     current_data = buf
     size_info.compressed_size += len(current_data)
 
     while len(current_data) > 0:
-      size_info.uncompressed_size += len(decompressor.decompress(current_data, CHUNK_SIZE))
+      try:
+        size_info.uncompressed_size += len(decompressor.decompress(current_data, CHUNK_SIZE))
+      except:
+        # The gzip stream is not valid for some reason.
+        size_info.uncompressed_size = None
+        size_info.is_valid = False
+        return
+
       current_data = decompressor.unconsumed_tail
 
       # Make sure we allow the scheduler to do other work if we get stuck in this tight loop.