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Bingo. Deployment with us is automated. I don't actually stay up to 3 AM. However, during the deployment the machine is automatically updated with new packages and the new version of the software, caches are cleared, it's restarted, etc. All of this probably takes 5 minutes at most, but still ... why do that in the middle of the day?

Also, we do a daily backup around midnight. If the deployment is botched, I can come in early in the morning, notice it and simply do a roll-back using the backup. Very easy.

Now, if you're actually staying up until 3 AM and doing things manually ... you need to automate things.

Depends on the type of site/application. If your application is managing customer data that can be updated 24 hours a day, a few minutes of down-time might be okay, whereas rolling back 6 hours of data (and losing it) is definitely not okay.

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