So I've got a Linode 128 running the 2.4.26-linode31-1um kernel that has been up for 114 days. I've never had a mysterious crash or performance that didn't meet my expectations.

So as I watch kernel's come and go, I wonder, why should I upgrade?

Since I haven't experienced any bugs or crashes, a large performance boost would be about the only thing that could convince me. Only trusted users have shell accounts, so the only vulnerabilities I have to worry about are remote ones.

When do I swallow my uptime pride and press the reboot button? (And how long does a reboot take anyway?)

The only possible problem is that 2.4.26-linode31-1um is no longer in caker's list of available kernels. If you check your configuration profile(s), I think you will find they have been set to use 'latest 2.4' when your current kernel was deleted from the list. If your Linode is rebooted unexpectedly, you are going to upgrade your kernel whether you like it or not.

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/ Peter