diff --git a/registry/storage/driver/azure/azure.go b/registry/storage/driver/azure/azure.go
index 930b76a17..bec2cf8e5 100644
--- a/registry/storage/driver/azure/azure.go
+++ b/registry/storage/driver/azure/azure.go
@@ -117,19 +117,33 @@ func (d *driver) GetContent(ctx context.Context, path string) ([]byte, error) {
 
 // PutContent stores the []byte content at a location designated by "path".
 func (d *driver) PutContent(ctx context.Context, path string, contents []byte) error {
-	if _, err := d.client.DeleteBlobIfExists(d.container, path, nil); err != nil {
-		return err
+	if limit := 64 * 1024 * 1024; len(contents) > limit { // max size for block blobs uploaded via single "Put Blob"
+		return fmt.Errorf("uploading %d bytes with PutContent is not supported; limit: %d bytes", len(contents), limit)
 	}
-	writer, err := d.Writer(ctx, path, false)
-	if err != nil {
-		return err
+
+	// Historically, blobs uploaded via PutContent used to be of type AppendBlob
+	// (https://github.com/docker/distribution/pull/1438). We can't replace
+	// these blobs atomically via a single "Put Blob" operation without
+	// deleting them first. Once we detect they are BlockBlob type, we can
+	// overwrite them with an atomically "Put Blob" operation.
+	//
+	// While we delete the blob and create a new one, there will be a small
+	// window of inconsistency and if the Put Blob fails, we may end up with
+	// losing the existing data while migrating it to BlockBlob type. However,
+	// expectation is the clients pushing will be retrying when they get an error
+	// response.
+	props, err := d.client.GetBlobProperties(d.container, path)
+	if err != nil && !is404(err) {
+		return fmt.Errorf("failed to get blob properties: %v", err)
 	}
-	defer writer.Close()
-	_, err = writer.Write(contents)
-	if err != nil {
-		return err
+	if err == nil && props.BlobType != azure.BlobTypeBlock {
+		if err := d.client.DeleteBlob(d.container, path, nil); err != nil {
+			return fmt.Errorf("failed to delete legacy blob (%s): %v", props.BlobType, err)
+		}
 	}
-	return writer.Commit()
+
+	r := bytes.NewReader(contents)
+	return d.client.CreateBlockBlobFromReader(d.container, path, uint64(len(contents)), r, nil)
 }
 
 // Reader retrieves an io.ReadCloser for the content stored at "path" with a
@@ -383,6 +397,14 @@ func (d *driver) listBlobs(container, virtPath string) ([]string, error) {
 }
 
 func is404(err error) bool {
+	// handle the case when the request was a HEAD and service error could not
+	// be parsed, such as "storage: service returned without a response body
+	// (404 The specified blob does not exist.)"
+	if strings.Contains(fmt.Sprintf("%v", err), "404 The specified blob does not exist") {
+		return true
+	}
+
+	// common case
 	statusCodeErr, ok := err.(azure.AzureStorageServiceError)
 	return ok && statusCodeErr.StatusCode == http.StatusNotFound
 }