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Time and time again, procrastination pays off. Sometimes I resist upgrading something because of annoying breaking changes.

Often, the impact of those changes is lessened in subsequent releases, making the dreaded upgrade a lot less painful.

Don't upgrade now what you can upgrade tomorrow. It'll be easier!*

*security patches excluded (and often they get backported so you can dodge the breaking changes in style!)
Consult your system administrator to determine if Procrastination™ is for you.