vCenter 5.5 Windows Server to vCenter 6.5 Server Appliance Migration - Preparation

OK so our VMware environment at work is still running on vCenter 5.5 on top of a Windows Server 2008 R2 server and the ESXi hosts on 5.5 too. Support for these ends on the 19th September 2018 so apart from extended our support the other option is to look at upgrading.

Our support agreement enables us to upgrade our licenses to the 6.x varients so I started to prepare everything for this migration which I will go into detail below.

First of all make sure you are eligible for the licenses. Either upgrade them if you can via a valid support agreement using your MyVMWare account or contact your VMware reseller to purchase the relevant keys for everything you want to upgrade. Once you have the license keys or have upgraded your existing ones you are ready to go in that respect.

In my instance I am upgrading a Windows Server 2008 R2 vCenter 5.5 install to the 6.5 VCSA migrating everything over using the essentials license key. All roles are installed on the one server so it’s a pretty easy migration compared to others who have the different components installed across multiple servers. 

In addition to this are 3 hosts currently running ESXI 5.5 with the Essentials Plus licenses over to 6.5 and one standalone host to ESXI 6.0 Standard (reason for this version is coming up).

Check your hardware can support everything. We have 3 x HP DL360 Gen 8 servers which can take the ESXI6.5 version but we also have a standalone host which we replicate all VM’s to with Veeam and this is a HP ML350 G8 which can only take up to version 6.0 U3. So use the VMware Hardware compatibility page to check your hardware is supported.VMWare Hardware compatibility

 Also check anything else which may interface with or be used with your environment. We have Veeam B&R 9.5 which fully supports version 6.5. Our SAN EMC-VNX-e is compatible with the later version so everything is OK to upgrade.

The one thing we have to be mindful of is updating the VM hardware version, we cannot go to the latest Hardware version 13 due to our replication host only being able to run ESXI 6.0 so we can only go up to version 11 to make sure our replicas will spin up if required. I believe there are workarounds for this but in the event of a disaster I just want to be able to turn a replica on and it work with minimal fuss. That being said we will not really miss any features version 13 brings so it’s not a major problem.

The migration supports going from 5.5 and 6.0 to VCSA 6.5. At this time you cannot upgrade to 6.5 on the Windows Server version then migrate to the VCSA.

If you have stuck to using the full C# client to manage vCenter in the past you will need to make sure you are ready to get to grips with the Webclient as that is the only way to manage your vCenter instance in 6.5.

Before upgrading make sure you have a backup of your vCenter server, mine is backed up using Veeam. I will also take a separate SQL backup of the VCDB and VUM database just in case and snapshot the vCenter server before migration. It looks to be a fairly simple way of rolling back but I like to make sure I have every eventuality covered.

Also you may want to rename your vCenter VM so when you migrate to VCSA you can keep your original name going forward. I added _OLD to the end of the current vCenter VM.

SQL Backup

Take a backup of both VUM and VC databases just to be on the safe side. Nothing should happen to these anyway they will still be present on the server but it’s always best to be more safe than sorry.



I backup to the local disk then copy them off onto another server once completed so they are out of harms way.

Backup of vCenter VM

Currently our vCenter 5.5 is running on a VM. This is backed up using Veeam B&R and the backup was successful so in the event of any major disasters we can use Veeam to roll the server back if required.

Snapshot of vCenter VM

Again I’m going to take a snapshot of the vCenter VM just before starting the upgrade and migration just as another failsafe. As mentioned before if for any reason things did fail it’s pretty easy to roll the process back but having a current snapshot of the VM just gives us another option if we needed it. I’d rather have plenty of options to go back to rather than none!

I’ll not teach you to suck eggs with this one but connect to vCenter web client and right click the VM containing vCenter and “Take Snapshot”

Rename vCenter VM

Rename your VM in the webclient if you wish to retain the VM’s original name after the migration to VCSA.



The upgrade process takes form in two stages, the first is where the new VCSA VM is created and the second is where the data is copied over to it and made live.


In the next blog post I'm going to go through Stage 1 with detailed screenshots to show the process as it was for me even at times when things don't go to plan or when things happen that are out of the ordinary.