Here is a message from a WordPress.com developer regarding uploading images from ScreenShot captor:

The screen capture program, ScreenshotCaptor.exe adds it’s executable name to the image metadata in the header which makes it look like there may be an embedded exe file in the image – a common way to distribute viruses. We therefore block the serving of such an image. When we resize the image, that metadata gets stripped, so the image serving works.

Is there a way to override this in the settings?

If it's commonly considered a security risk, won't it better to avoid this altogether?