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How Often Should I Update Hass.io?

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@CaptTom wrote:

I’m running Hass.io on a Raspberry Pi 3 B+. I installed it almost a year ago. I’ve been keeping HA up to date by updating it (after checking for breaking changes!) each time I’m notified to do so.

But I never saw anything about updating the OS. This came up in a recent post, and I noticed my Hass.io was WAY out of date. I took a gamble and ran the update. No problems so far (whew!)

As I type this, the forum software is showing me lots of threads reporting problems updating Hass.io. That sort of makes me nervous.

So, do I need to update regularly? How regularly? Are breaking changes common? Where would I even find them? The HA update notices include a link to breaking changes I can review.

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