Spinning wheel when printing to PDF / saving attachments more than once

So I have a recent problem: in Safari, Chrome, and Mail, if I try to print to PDF or save an attachment, everything goes fine. If I attempt to do so more than once (even leaving it a little while) during an application session, it then causes the spinning wheel to appear and the application to become unresponsive. I have to force quit, reload, etc, and then it lets me print to pdf / save an attachment fine. It's extremely annoying and any advice would be appreciated.