diff --git a/Tools/px_uploader.py b/Tools/px_uploader.py
index a8f0b7ed44..1154506a11 100755
--- a/Tools/px_uploader.py
+++ b/Tools/px_uploader.py
@@ -488,9 +488,18 @@ class uploader(object):
                 print("FORCED WRITE, FLASHING ANYWAY!")
             else:
                 raise IOError(msg)
+
+        # Prevent uploads where the image would overflow the flash
         if self.fw_maxsize < fw.property('image_size'):
             raise RuntimeError("Firmware image is too large for this board")
 
+        # Prevent uploads where the maximum image size of the board config is smaller than the flash
+        # of the board. This is a hint the user chose the wrong config and will lack features
+        # for this particular board.
+        if self.fw_maxsize > fw.property('image_maxsize'):
+            raise RuntimeError("Board can accept larger flash images (%u bytes) than board config (%u bytes). Please use the correct board configuration to avoid lacking critical functionality."
+                % (self.fw_maxsize, fw.property('image_maxsize')))
+
         # OTP added in v4:
         if self.bl_rev > 3:
             for byte in range(0, 32*6, 4):