"commonly used (open source?) software" is a bit vague, for the rest of the answer I'm assuming you are talking about a piece of software that somehow relates to programming. If not, I'm not so sure why you'd want to ask about it on Stack Overflow.
First:
- Find the project's issue tracker
- If the bug isn't reported, report it
Then:
- If there weren't any workarounds suggested on the issue tracker (or the bug wasn't reported at all), feel free to ask on Stack Overflow for workarounds (don't forget to link back to the bug report).
- If there were workarounds on the issue tracker, but they didn't work for you, free to ask on Stack Overflow, but please explain in detail why the proposed workarounds didn't work for you.
If you find a great answer on Stack Overflow, you'll get bonus unicorn points if you link to it in the bug report.
Also:
If you found an awesome workaround, you might want to risk posting a Q&A combo. The community generally frowns upon self answered questions that aren't stellar, so if you decide to go this way:
- Your question should stand on it's own,
- Your answer should be awesome.