(Is There a) Rule of Thumb for Upgrading?

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TL;DR
Given so many update notices for different software, when is it a good idea to update/upgrade?
Ok, so the latest is SSMS and SQL Server notices urging me to update. Obviously the general question of when does it make sense to upgrade/update is too broad. Any tips, rules of thumb , for when it makes sense to update/upgrade?
 
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Always for bug fixes. Usually for minor improvements.
 
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I try to only update when I can afford the time and there's a pause in my project that depend on it.
i.e. assume the update is going to go pear-shaped and will need some baby-sitting.
 
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When the annoyance of not doing it becomes greater than the annoyance of doing it.
 
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When you upgrade without much planning or experimenting things can go wrong In your project. A new an improved compiler may have deprecated some api that your program relies on heavily prompting you to rewrite those parts.

Or the new compiler has new command line flags that your build tool can’t set unless you update the build tool too.

Updates can cause a cascading effect that can derail your project and should be updated after the project is delivered And before another is started
 
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jedishrfu said:
should be updated after the project is delivered
Unless the upgrade will improve the project sufficiently to warrant instigating it as its own phase (sprint?) .
All dev production should stop until the update is complete and regression tested.
 
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There are exceptions to every guideline.

I just wanted to point out that updates done mid project unless absolutely undeniably irrevocably needed should be deferred to the between projects time lest you affect your delivery schedule or even the delivery of the product or suite of products.

nuf said.
 
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We are talking about database software here that runs independently from any project that @WWGD may be working on. Within main version streams there is no change to the API that can break anything you are working on (unless you are patching SQL Server itself, which I don't think is the case).

You should keep SQL Server updated to the latest release for your version (ie. 2012, 2014, 2016, 2017, 2019 and 2022). Consider timing for updating to the next version, bearing in mind the need to regression test whatever you are running/developing that depends on it.

SSMS can be updated to the latest version at will - if something goes wrong you can just delete it and reinstall the old version (make sure you have access to the install file for that of course).
 
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