diff --git a/gelbooru_poster.py b/gelbooru_poster.py
index 577cf71..26e67bc 100644
--- a/gelbooru_poster.py
+++ b/gelbooru_poster.py
@@ -75,13 +75,27 @@ class BotInstance:
     # Download and post the image to Misskey
     def post_image(self, image_url, image_src, image_rating, log_file):
         image_found = False
-        file_presence_check = requests.post(self.misskey_url + "drive/files/find", json = {"name": os.path.split(image_url)[-1], "i": self.misskey_token})
+        image_fname = os.path.split(image_url)[-1]
+
+        #Check if the image is already uploaded with original extension
+        file_presence_check = requests.post(self.misskey_url + "drive/files/find", json = {"name": image_fname, "i": self.misskey_token})
         if file_presence_check.status_code != 200:
             image_found = False
         else:
             file_presence_json = file_presence_check.json()
             image_found = len(file_presence_json) > 0
 
+        #Check if the image is already uploaded with .jpg extension
+        if not image_found:
+            file_presence_check = requests.post(self.misskey_url + "drive/files/find", json = {"name": image_fname + ".jpg", "i": self.misskey_token})
+            if file_presence_check.status_code != 200:
+                image_found = False
+            else:
+                file_presence_json = file_presence_check.json()
+                image_found = len(file_presence_json) > 0
+                if image_found:
+                    image_fname += ".jpg"
+
         if not image_found:
             # If the file is a static image, download, optimize and post it to Misskey
             if image_url.endswith(".jpg") or image_url.endswith(".jpeg") or image_url.endswith(".png"):
@@ -123,7 +137,7 @@ class BotInstance:
                         return False    
                 else:
                     # Submit a /drive/files/create request to Misskey
-                    create_file_request = requests.post(self.misskey_url + "drive/files/create", data = {"name": os.path.split(image_url)[-1], "i": self.misskey_token, "isSensitive": str(image_rating != 'general').lower()}, files = {"file": open("image.jpg", "rb")})
+                    create_file_request = requests.post(self.misskey_url + "drive/files/create", data = {"name": image_fname, "i": self.misskey_token, "isSensitive": str(image_rating != 'general').lower()}, files = {"file": open("image.jpg", "rb")})
                     # If error, print error and exit
                     if create_file_request.status_code != 200:
                         print(self.cfg_name + ": Error: ", file=log_file)
@@ -151,7 +165,7 @@ class BotInstance:
         attempts = 0
         while True:
             # Get the file ID using the /drive/files/find request
-            file_id_request = requests.post(self.misskey_url + "drive/files/find", json = {"name": os.path.split(image_url)[-1], "i": self.misskey_token})
+            file_id_request = requests.post(self.misskey_url + "drive/files/find", json = {"name": image_fname, "i": self.misskey_token})
             # If error, print error and exit
             if file_id_request.status_code != 200:
                 print(self.cfg_name + ": Error: ", file=log_file)