Thanks, Matt. I did try the update procedure from the handbook and found the 
instance hanging on boot with a repeated socket error. If I have to rebuild 
from scratch, I’d prefer to find some jail/deployment-automation so I don’t 
have to manually rebuild everything on each release. FWIW, I did have to 
recreate the instance when moving from 10 to 11.

Cheers,

-Brian

> On Dec 19, 2018, at 7:33 AM, Matt Garber <matt.gar...@gmail.com> wrote:
> 
> 
>> On Dec 19, 2018, at 1:50 AM, Brian Neal <br...@aceshardware.com> wrote:
>> 
>> I’m looking for advice on doing a release upgrade of a running instance.  It 
>> looks like the normal procedure using freebsd-update requires a reboot 
>> between invocations of the install command, but after the first reboot, most 
>> of the userland is non-functional, including most importantly sshd. Is it 
>> safe to run the install commands back to back without rebooting?  Or is the 
>> only safe procedure to build a new instance from scratch for each release?
> 
> Brian,
> 
> It’s not true that after the first reboot the userland is non-functional; 
> sshd and friends should still be working fine. The first reboot switches you 
> to the 12.0 kernel, which is necessary as the first step before upgrading the 
> userland to 12.0 – and of course potentially using `pkg-static` or ports to 
> rebuild/reinstall your packages/ports against the new ABI.
> 
> If you’re running any kind of public-facing service, the safest method in my 
> opinion *with as little downtime as possible* is to deploy a new instance and 
> then point to it once everything is successfully reinstalled (e.g., DNS 
> change, elastic IP change, elastic load balancer, etc.). Otherwise, the 
> “safe” method to upgrade in place is to follow what the handbook says, 
> including when to reboot between invocations of `freebsd-update`. As long as 
> you follow exactly when it instructs a reboot, and when to upgrade/reinstall 
> userland and packages/ports, you should be fine. If you’re still nervous, 
> just snapshot your boot EBS volume first as an extra precautionary measure, 
> and destroy it once you verify everything post-upgrade.
> 
> 
> --
> Matt Garber
> 

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