Good steps to do when upgrading VCSA 5.5

First of all, I recommend setting the VMX advanced setting on the VCSA device explained here

http://kb.vmware.com/selfservice/microsites/search.do?language=en_US&cmd=displayKC&externalId=196

This will make repeated characters go away. The VM has to be off to either edit the VMX file or add 


My steps to have a great chance of success:

0 Have a backup plan

Take a snapshot of your Vcenter for painless reversal in case of trouble, and make sure your latest VM backup is a good one.

1 Confirm your root account works

easy enough through VAMI or on the VM console. If it's not working this is the KB you want.

http://kb.vmware.com/selfservice/microsites/search.do?language=en_US&cmd=displayKC&externalId=2069041

Since you do this with vCenter unavailable, make sure you know on what ESXi host your vcenter is, and connect to it directly.

If you really can't even login to Grub try the SUSE rescue CD like explained here - I haven't had to do it yet so I can't certify it.

2 Confirm current build and update availability

Also easy to do through VAMI. Write it down just in case you need to call support.

3 Confirm space, in VAMI and SSH shell

To enable shell, you have to enable it in the VAMI - check https://pubs.vmware.com/vsphere-55/index.jsp#com.vmware.vsphere.vcenterhost.doc/GUID-8DC793FF-1E00-43A1-B85C-070414B9F9B0.html

I like checking through the shell because it shows more than the VAMI interface, which only shows System, Database, Logs and Coredumps. This is just making sure some other disk isn't full.

What you want to see if enough space in System and Database and Logs - running out of space on any of these could case the update to fail!

If you ran out of disk space and you can't move/delete something (like old syslogs you no longer need) I like this gParted method better than VMware's make another disk and copy everything over method.

4 Update and reboot

Check for updates (you have to have internet connection)
Install updates (normally you get logged out when it completes)
Log back in, browse the Update tab and it should have a note saying a reboot is needed to complete
Reboot from the system tab and monitor the VM console for any scary messages, and confirm the VCSA boots properly again.

5 Test and cleanup

Login to VAMI again and check the services are up and the new version is displayed
Login through web client and C# client, make sure AD authentication is working if you have it setup
Browse through the web client to the vCenter, Monitor tab, and "Service Health" sub-tab. You should have green checks all the way.
Disable any SSH processes you had to enable.
Delete the snapshot and celebrate :D