When should I upgrade Android?

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AC Question

I have a new HTC Desire 320 running Android 4.4.2. This is my first cell phone so I'm hazy on some of the basics. Should I be getting into the habit of upgrading the OS periodically? If yes, what should prompt me to upgrade the OS?

For example, I know that Android 5.1 exists. Should I upgrade my phone to use 5.1 now, even though I'm not having any problems with 4.4.2, just because I know there's a newer version of the OS available? Or should I wait until some other event before upgrading the OS?
 
Welcome to AC.

You will normally be notified of any updates, or you can check for them in Settings, About Phone, Software Updates.
Kitkat 4.4.2 is a perfectly good version of the OS, and not particularly old.

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