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Selfhosted
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As long as updates work between any two versions, or there's a clear upgrade path, I don't really care. I don't update my services on any particular schedule, so it doesn't matter much to me.
However, you should have a mechanism to inform users of important updates, like patches to known exploits. Don't spam me, but a nudge if I'm outside of some support window will probably get me to upgrade.
My upgrade cadence is probably every 3-6 months. I'll do system upgrades more often, but I try to avoid breaking my docker stuff.