I just gave it a try (version 11.0.2201.20436 testing via Google Chrome).
When I set the field configuration to "pdf" I was able to attach a file regardless of whether I set it's extension to pdf, PDF, or Pdf. However, when I changed the configuration to either "PDF" or "Pdf" if failed no matter which way I listed the extension on the actual file.
Unless I'm mistaken, in both the classic designer and the new designer, Forms is just leveraging the standard HTML functionality for <input type="file"> with the accept parameter for file types and not something uniquely designed. So you'd think it would behave like any other file input on any other website. However, I think they might be doing some sort of custom validation on the field, and that is where I think it is failing.
For one thing, Forms is tweaking the values you are putting for the file types in order to match how the html expects it to be listed. For example, if you want to accept txt, docx, and pdf you would list them as "txt,dox,pdf" in Forms, but on the browser it'll end up showing as ".txt,.docx,.pdf" which is how the field should look in HTML. If you try listing them as ".txt,.docx,.pdf" in Forms then they end up having extra periods in the browser ("..txt,..docx,..pdf") and then they don't work.
In a quick test with a basic HTML file (I just made it say the script below) it wasn't case sensitive.
<html><body><input type="file" accept=".PDF"></body></html>
So, I believe that despite the fact that the field in HTML itself shouldn't be case sensitive, it does seem like the new designer in forms doesn't like it unless you list the values in lower case, and I suspect it is tied more to the field validation that to the actual field itself.
EDIT TO ADD: I did notice on the classic designer that when it added the periods to the allowed extensions, it also made them lowercase (changing "txt,docx,PDF" to ".txt,.docx,.pdf"). It still shouldn't matter to the browser, but there is that difference. I still think it's some sort of validation script of the new designer, and not the actual file input field, that would be causing any problems.