I have a VPS hosted somewhere running Ubuntu 10.04. How do I know when to patch the system? Is there a notification system analogous to, for example, Mac OS or Windows warning me (through email) to apply updates?
4 Answers
I'll recommend the apticron
package.
It'll check for updates every day, and hit you with a nicely formatted email with package names and change logs when there are new ones pending (using the DIFF_ONLY
option).

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Install apticron.
Sends an e-mail daily with details of required updates, perfect for servers.

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Ubuntu warns you while you login to a shell. And you can setup Ubuntu so that it automatically installs security fixes.

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You could use a simple cronjob to notify yourself about updates. Depending on the distribution you use, the package-manager will show you the available patches.
On ubuntu you could create a script like this:
#!/bin/bash
aptitude update >/dev/null
aptitude dist-upgrade -s
You should make sure that you get the cronjob emails. Run this script once a week via cron, and you should receive a mail with a list of available updates.

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