How to Upgrade from VCSA 5.5 to 6.0 – Lab Time (ESX Virtualization)

Upgrade from VCSA 5.5 to VCSA 6.0 is supported scenario. In fact you can upgrade to VCSA 6.0 from 5.1U3 upwards. The upgrade process is quite straightforward, but I still do the walk through to see if any problems will arise in the lab.

Upgrade from VCSA 5.5 to VCSA 6.0 is not in place upgrade but rather side-by-side upgrade. We setup a new VCSA 6.0 appliance which will pull all configuration of the current environment from the old VCSA 5.5 appliance (including historical/performance data).

If you running production environment you will certainly wait for a while, untill your backup vendor updates to the latest vSphere release and also if any gotchas surface out through different testing or lab environments like mine for example. Upgrade to the latest vSphere 6 should not be difficult by itself, but one must be absolutely sure that all the backup/replication/monitoring products that are currently in the environment can continue to “cooperate”….

Check this before starting the upgrade:

  • Do a backup or create a snapshot of your existing VCSA.
  • You should check that the vCenter Server SSL certificate for the curent environment is valid and without miss-configuration. There is a VMware KB  2057223 .
  • Verify that the clocks of all machines on the vSphere network are synced. Synchronizing Clocks on the vSphere Network .
  • Verify that the ESXi host on which you deploy the vCenter Server Appliance is not in lockdown or maintenance mode.
  • In case you are on external database (SQL for example), make sure that you back it up.
  • The upgrade outline can be found at the vSphere 6 documentation page

Here is what I’ve done to upgrade to the latest vSphere 6.0 vCenter (VCSA). After downloading the VCSA 6.0 iso image from VMware (The latest one is the VMware-VCSA-all-6.0.0-2562643.iso version), there is just very few steps to do:

1.Mount the ISO and go to the vcsa folder to install VMware Client Integration plugin.

2.Once done, double-click the vcsa-setup.html file located at the root of the DVD…

3.This bring the famous window offering you to do a clean install or an upgrade. You might have seen it in my detailed post abouthere.

You’ll get a nag telling you basically that you’ll have to be on VCSA 5.1 U3 or VCSA 5.5 in order to upgrade to VCSA 6.0… That’s the only options. If you’re on other version, you must first upgrade to those two supported ones…

VMware has a new KB article on the simple upgrade too.

You’ll need those informations to carry on:

vCenter Applicance

  • Appliance Version
  • vCenter Server IP or FQDN
  • vCenter Administrator Username
  • vCenter Administrator Password
  • vCenter HTTPS Port
  • Appliance Root password (when using https://vc-address:5480

Source ESXi Host

  • ESXi host IP or FQDN
  • ESXi host username
  • ESXi host password

Well, my upgrade did not went as I wanted to and I was facing with a blocking error.

The problem says:

vCenterServer FQDN vcsa55.lab.local does not match DNS servers “localhost.localdom,localhost” and ip addresses “” from VC certificate

Examine the VC certificate and make sure it is valid and point to vCenterServer FQDN.

Well, I was using the default certificates on that VCSA VM since 5.0 I think, and the VCSA got regullary updated to the latest release. Never thought that there is an issue in certificate config… Oh well. But the error blocked my progress…

What finally solved the problem was to “detach” the VCSA 5.5 from my AD domain… You do that when login into your VCSA at https://IP_of_your_appliance:5480/ and you go to the vCenter server TAB and Authentication sub tab.

Then I was able to continue the wizard normally… I also checked the box (you see it unchecked in the image above) to Migrate performance and other historical data…

Next screen is the usual screen inviting for the size of the appliance and the environment…

Next screen… storage.. Nothing special…

Next page is networking. Note that we actually do not do in-place upgrade but rather side-by-side upgrade (if I can say that). We setup new appliance which will pull the historical/performance data and configuration of all virtual environment from the old VCSA 5.5 vCenter appliance.

So far so good… Last recap screen and …

And then sit back and have a coffee…

Oh, almost perfect… All it took me about 20 min to upgrade…  After reboot you can see that the new VCSA appliance has a new look similar to ESXi console, but with blue color. There is not much you can configure by hitting the F2. You can  change network settings and enable BASH Shell and SSH for the appliance for troubleshooting)

The admin access we use to have through the 5480 is no more. The only way to have GUI admin is through the vSphere Web client where you can join the AD, but this is easy. If you try to hit the http://ip_of_your_appliance, you’ll get to a nice web page from where all can you do is to click a link towards vSphere web client or go to the documentation page… Oh well, you can also browse datastores…


The upgrade process is simple when matching all pre-requisites and your environment is healthy. My certificate problem could have been detected if I would have followed the VMware Knowledge Base article 2057223 . The process took me 15-20 min to get through, plus some time for troubleshooting. Not so bad.

Minimum 8Gb of RAM is required to deploy the VCSA for Tiny environment, and there are 3 other sizing options there.