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I have a couple of questions regarding best practices for updating an ubuntu web server. A server that is hosting a live website that would be very problematic should the server "go down". I am a web developer, not a full time admin, though I do spend a fair amount of time doing "dev-ops".

By updates I'm referring to the ones indicated upon SSH login... 

48 packages can be updated.
35 updates are security updates.

Questions

  • How often should one perform package updates to an ubuntu server, responsibly?
  • What is the risk level of these package updates?
  • Should a roll back strategy be in place in the event of an issue?
    • If so, what kind of rollback strategy should be used. (I use chef to "spin up" new servers as needed, and all site related files are backed up daily) I am confused when it comes to how you would "roll-back" or "restore" linux package updates.

I'm sure there is a variance in terms opinion on this subject. I apologize in advance if this isn't appropriate for serverfault.com

Thanks.

Michael Bopp
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  • Do you have *any* sort of backup system in place? What happens if the server crashes? – Nathan C Jan 23 '14 at 15:39
  • I DO have a robust backup in place for all our servers that is set up with Chef when creating. It involves duplicity etc. BUT, it only backs up database and site files. It's not an image of the whole server. – Michael Bopp Jan 23 '14 at 18:44
  • Typically package updates are tested before being released to the mainstream package manager, so you should be fine. Check and re-check which packages are affected to see if anything (like PHP, for example) would break your website. – Nathan C Jan 24 '14 at 15:08

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