diff --git a/backend/agents/client/chat.go b/backend/agents/client/chat.go
index 6f8cadd..23ccc99 100644
--- a/backend/agents/client/chat.go
+++ b/backend/agents/client/chat.go
@@ -216,6 +216,12 @@ func (chat *Chat) AddImage(imageName string, image []byte, query *string) error
 		index += 1
 	}
 
+	if len(extension) == 0 {
+		// Hacky! It seems apple doesnt add extension.
+		// BIG TODO: take better metadata from the image.
+		extension = "png"
+	}
+
 	messageContent.Content[index] = ImageMessageContent{
 		ImageType: "image_url",
 		ImageUrl: ImageMessageUrl{
diff --git a/backend/main.go b/backend/main.go
index 31cd2a7..18a878a 100644
--- a/backend/main.go
+++ b/backend/main.go
@@ -91,6 +91,10 @@ func main() {
 
 		// TODO: this could be part of the db table
 		extension := filepath.Ext(image.ImageName)
+		if len(extension) == 0 {
+			// Same hack
+			extension = "png"
+		}
 		extension = extension[1:]
 
 		w.Header().Add("Content-Type", "image/"+extension)