Illegal image type error message not shown if other error message already present on screen

If you have an image field configured to require a limited set of types and have another constraint on file size and/or dimensions, the file type error message will only be shown to the user if it is the only issue.

Given the following configuration:

Files must be less than 2 MB.
Allowed file types: png gif jpg jpeg.
Images must be larger than 550x244 pixels.

If you try to upload a tif file(regardless of file size) you will see an error message saying that the tif type is not allowed.

If you first try to upload a file that is too large. You will see a message saying the file is too large. If you then try to upload a tif file, you will still see the original message about the file being too large with no indication as to while your second file was denied.

It seems to have to do with the fact that the file type check is happening on the fly which the file size error is happening after clicking the upload button.