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Regarding security, Windows 8 has quite some problematic aspects.
One of those also introduces a functionality problem when using Academic Signature:

By default extensions are hidden in Windows 8 File Explorer. If for example a file has double extensions and is named "bugger.jpg.exe",
Windows will show it to you either as "bugger.jpg" or just as "bugger" using an icon that insinuates it would be a jpg image. (Double extensions are not unusual on other OSses or the internet.)
Yet Windows 8 treats it according to its last hidden! file extension ".exe" and will try to run it if you click on it.
Bear that in mind: It hides one component from you, shows you other one, but treats it according to the one it hides from you!

Besides being a bad security risk and a beacon of transparency, this also can mess up Academic Signatures file selection procedures. Academic Signature relies on double extensions to treat a file like "example.pdf" and denote its digital signature "example.pdf.ecsg" or "example.pdf.ects" to denote the time stamp. (You are still up for a smooth ride using encryption though, since this does not use double file name extensions.)

Since I cannot see myself patching dirty behavior with equally dirty "counter hacks", the best I can do for now is to refer you to this webpage http://www.howtohaven.com/system/show-file-extensions-in-windows-explorer.shtml . This page will walk you through a procedure to make File Explorer always show extensions which would also mitigate the disturbance of Academic Signature on Windows 8.

If you don't want to do that and leave the Windows 8 defaults on, you can always manually rename signature and time stamp files to single extension names, e.g. "example_pdf.ecsg" and also explicitly edit the suggested signature-file line in the dialog for verifying signatures.
I apologize for the inconvenience, but please don't blame me!

I would like to encourage you to migrate to a public license open source operating system for your computer ;-)