Various upgrading issues

[tin]

I'm currently attempting to upgrade a Zimbra 8.6.0 on Ubuntu 14 to something more up to date....

First I hit the problem of the proxy not being enabled - this is a standalone server - so I followed a guide, got the proxy enabled, but then discovered I couldn't log in via the proxy. It kept telling me I needed to enable cookies to log in.
"Fixed" that by running the proxy on a different port and moving the real web server back to 80.

Next I upgraded to 8.7.11 (because I already had it downloaded from a previous attempt). This appeared to work fine, though the proxy process didn't start. Manually starting it gave errors about various nginx configs. It first didn't like the zm_lookup URL. I just commented out the include line for that entire file. Next was various references to "chunkin". I gather this is no longer needed. I just commented out the sections referring to "chunkin", and everything seemed to work.
We never used the proxy before, so I don't actually care about these proxy configs - is there a way to reset just the proxy configs back to a "default" state?

And finally, I'm concerned that if I do the next stage of upgrading the OS, these pre-existing issues with the proxy will result in even more breakage. Should I be concerned, or just do it?

[phoenix]

There's two problems for me in this scenario. The first is that you're using Ubuntu, I'm not a fan of that because of the poor package management system it uses and I prefer CentOS. The second is that, as far as I'm concerned, it's bad practice to upgrade the underlying operating system when you rely on that server. Best practice would be to get your ZCS installation moved to a new server, for that I'd recommend (as I always do) using the ZeXtras Migration Tool to move your ZCS server to a clean installation of ZCS 8.8.6 on a new server. I'd recommend using CentOS7 but obviously you can use whatever you're used to.

[bgszim]

I've had problems with Proxy settings under 8.6 with a Standalone server too. It was a simliar port problem as you describe. I cant remember how i've fixed it but after that i've decided to make all the future updates for others servers in a ...more segmented way. First installing missing proxy/memcache modules - waiting a few weeks - upgrade Zimbra to 8.8.6 --- waiting a few weeks months --- upgrade from Centos 6 to centos 7.

Prior to that i've had this Zimbra Installation on a Centos 5 Host running for 3 years without any problems with upgrade; then migrated via the old rsync method to a centos 6 Server, again no problems with zimbra upgrades. The first time in 8 years i was running into problems while upgrading zimbra was because of the proxy/memcache stuff.