diff --git a/mautrix_telegram/config.py b/mautrix_telegram/config.py
index 8752f048..5093f02c 100644
--- a/mautrix_telegram/config.py
+++ b/mautrix_telegram/config.py
@@ -138,6 +138,7 @@ class Config(BaseBridgeConfig):
         copy("bridge.invite_link_resolve")
         copy("bridge.inline_images")
         copy("bridge.image_as_file_size")
+        copy("bridge.image_as_file_pixels")
         copy("bridge.max_document_size")
         copy("bridge.parallel_file_transfer")
         copy("bridge.federate_rooms")
diff --git a/mautrix_telegram/example-config.yaml b/mautrix_telegram/example-config.yaml
index 054156fb..1789cfc5 100644
--- a/mautrix_telegram/example-config.yaml
+++ b/mautrix_telegram/example-config.yaml
@@ -214,6 +214,8 @@ bridge:
     inline_images: false
     # Maximum size of image in megabytes before sending to Telegram as a document.
     image_as_file_size: 10
+    # Maximum number of pixels in an image before sending to Telegram as a document. Defaults to 1280x1280 = 1638400.
+    image_as_file_pixels: 1638400
     # Maximum size of Telegram documents in megabytes to bridge.
     max_document_size: 100
     # Enable experimental parallel file transfer, which makes uploads/downloads much faster by
diff --git a/mautrix_telegram/portal.py b/mautrix_telegram/portal.py
index 31f25117..b4fa3db8 100644
--- a/mautrix_telegram/portal.py
+++ b/mautrix_telegram/portal.py
@@ -1516,6 +1516,7 @@ class Portal(DBPortal, BasePortal):
             w = h = None
         file_name = content["net.maunium.telegram.internal.filename"]
         max_image_size = self.config["bridge.image_as_file_size"] * 1000**2
+        max_image_pixels = self.config["bridge.image_as_file_pixels"]
 
         if self.config["bridge.parallel_file_transfer"] and content.url:
             file_handle, file_size = await util.parallel_transfer_to_telegram(
@@ -1548,12 +1549,14 @@ class Portal(DBPortal, BasePortal):
             file_size = len(file)
 
         file_handle.name = file_name
+        force_document = file_size >= max_image_size
 
         attributes = [DocumentAttributeFilename(file_name=file_name)]
         if w and h:
             attributes.append(DocumentAttributeImageSize(w, h))
+            force_document = force_document or w * h >= max_image_pixels
 
-        if (mime == "image/png" or mime == "image/jpeg") and file_size < max_image_size:
+        if (mime == "image/png" or mime == "image/jpeg") and not force_document:
             media = InputMediaUploadedPhoto(file_handle)
         else:
             media = InputMediaUploadedDocument(