Will begin testing on my Proxmox…
I upgraded pr latest proxmox as well and it’s working fine. Also a bullseye vm with supervised also working fine.
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Idem. I upgraded my HA vm to bullseye, and proxmox environment to v7. Everything OK but the warning in supervisor.
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I’m going to do a new install now with Debian 11. Installing Debian 10 which might be only supported (officially) for another 4 months by home assistant (ADR0014) doesn’t make sense at all.
So benefit is definitely to be future proof 
Sure, I would probably do the same for a new install. But as for an existing installation on Debian 10 which works without any hiccups worth to mention I see no reason to upgrade now since HA Supervised on Bullseye is not officially supported yet.
Sure, actually Debian 11 (bullseye) is not yet released (but today is the day) and supporting not released software is rather difficult 
I ment HA Supervised on Bullseye is not officially supported yet by the Home Assistant dev team.
It’s not but I just upgraded a supervised dev instance I had running in a VM on Buster to bullseye and it upgraded without a hitch. Supervisor says unsupported but not unhealthy. I expect that there will be a supervisor update soon that will support bullseye. Anyway, I just started the upgrade process for my production supervised install cos I’m a thrill seeker and that’s how I roll…
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Fair enough. And judging of the many of your posts is showing that you know exactly what you are doing (but not blindly copy/paste things) and you wont whine n’ grief if something is not working as expected and blame the devs for it 
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Yeah it was totally uneventful. As expected I am now unsupported but not unhealthy. There have been a rush of supervisor updates recently but none for a couple of weeks so I suspect they are working on an update soon… The only issue I have is the cockpit package isn’t working but it didn’t work for some reason on a new install either so I’m following that up with the cockpit people but that’s nothing to do with HA. HA and everything else is working like nothing changed.
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I hope requirements will be updated (so ‘at least Debian 10’), as it would be nice to be able to upgrade OS.
I updated my server to Debian 11 yesterday rather than changing the repos from “stable” to “oldstable”.
All went well except that my HASS on docker-compose does not complete startup after a server restart.
It does complete startup though with:-
docker-compose restart
That’s not supervised though is it? All my docker stuff is running fine and my supervised restarted correctly after I rebooted my nuc
No it isn’t
Bullseye
Two weeks ago Debian 11 (Bullseye) was released. The upcoming version of the Supervisor will recognize that version as a supported Operating System. This means that if you are running Home Assistant Supervised, you can start upgrading that.
Support for the previous version (Debian 10 (Buster))is now deprecated and will be removed in the first version of the Supervisor after the 4 months grace period. This means that within the next 4 months you need to update to Debian 11.
Plenty of time left (as I wrote it already further up) 
Updated one of my dev instances this morning and it’s completely hosed. To be fair, I can’t recall what I have done to it over time, so I’ll pull it down and rebuild it.
Debian itself upgraded perfectly, but nothing works post-upgrade, insofar that I can’t even get it to serve me a basic web page, be it dockerised or native…
I updated this morning without any problems. Every thing just worked instantly after final reboot. I didn’t expected that but very happy. I followed these steps www.linuxtechi.com/how-to-upgrade-debian-10-to-debian-11/amp/
If you cannot even connect to a basic web page you may have the same problem I had when I upgraded to Debian 11
I was using nginx as a reverse proxy.
Debian 11 uses a later version of php so I had to edit the php version in the nginx .conf files.
I ended up building a new dev instance, and upgraded it using the above link (about a week ago), and it went through fine - no idea why it didn’t work the first time. My prod instance on my NUC also upgraded smoothly without any serious jiggery pokery, aside form having to add the non-free repo’s to add in the Realtek firmware, which I never did when I first built it