Troubleshoot Is it a security risk using a old version of a program or application?

Well, it is... and it's not.

The main reasons why newer software versions are released are: bug fixes/security patches and new features/modules for it.

As for the first reason, I might say it's a must to update it. You can check the logs and see what were they main changes or fixes in the new version and then choose wether to update or not.
For the second reason, it's entirely up to you. If we're talking about antivirus/antimalware solution, as long as your virus database are up to date, you should be statically protected. But you may be missing new modules or features updates that can dynamically protect you better.

Oh, and don't forget to report the bugs you found on the new version, so they can fix it soon! :=)
 
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How much so though ?
If the software in question does not have an access to the internet, like it is blocked in the firewall, not so much. It could still be exploited by a malware downloaded via a browser, but it is unlikely. Not to mention, the less known software, the less likely it will be exploited.

You might experience glitch, bug or crash that can be fixed by updating to the latest version.
On the contrary, a lot of software works perfectly fine, but it starts crashing or causing bugs, because of new features, like CCleaner.
 
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It depends a lot what software it is. Some software is pretty safe and/or is not targeted by malware, so you can use older versions.
If it is Adobe PDF reader, get the latest version. If it is a little freebee audio converter from wav to mp3 that no one ever heard of, you can use an old version.
 
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