Yes that’s not a typo…this post is focusing on upgrading Windows vCenter 5.5 to 6.0 via an in-place upgrade. There is the option to use the vSphere 6.0 Update2M build with the included Migrate to VCSA tool to achieve this and move away from Windows, but I thought it was worth documenting my experiences with a mature vCenter that’s at version 5.5 Update 2 and upgrade that to 6.0 Update 2. Eventually this vCenter will need to move off the current Windows 2008 RTM server which will bring into play the VCSA migration however for the moment it’s going to be upgraded to 6.0 on the same server.

With VMware releasing vSphere 6.5 in November there should be an increased desire for IT shops to start seriously thinking about moving on from there existing vSphere versions and upgrading to the latest 6.5 release however many people I know where still running vSphere 5.5, so the jump to 6.5 directly might not be possible due to internal policies or other business reasons. Interestingly in the rough numbers, I’ve got an active Twitter Poll out at the moment which after 100 votes shows that vSphere 5.5 makes up 53% of the most common vCenter version, followed by 6.0 with 44% and 6.5 with only 3%.

Upgrade Options:

You basically have two options to upgrade a Windows based 5.5 vCenter:

My approach for this particular environment (which is a NestedESXi lab environment) was to ensure a smooth upgrade to vSphere 6.0 Update 2 and then look to upgrade again to 6.5 once is thaws outs in the market. That said, I haven’t read too many issues with vSphere 6.5 and VMware have been excellent in ensuring that the 6.5 release was the most stable for years. The cautious approach will still be undertaken by many and a stepped upgrade to 6.5 and migration to the VCSA will be common place. For those that wish to move away from their Windows vCenter, there is nothing stopping you from going down the Migrate2VCSA path, and it is possible to migrate directly from 5.5 to 6.5.

Existing Component Versions:

vCenter 5.5 (2001466)

ESXi 5.5 (3116895)

SQL Version Requirements:

vCenter 6.0 Update 2 requires at least SQL Server 2008 R2 SP1 or higher, so if you are running anything lower than that you will need to upgrade to a later service pack or upgrade to later versions of SQL Server. For a list of all compatible databases click here.

vCenter Upgrade Pre-Upgrade Checks:

First step is to make sure you have a backup of the vCenter environment meaning VM state (Snapshot) and vCenter database backup. Once that’s done there are a few pre-requisites that need to be met and that will be checked by the upgrade process before the actual upgrade occurs. The first thing the installer will do after asking for the SSO and VC service account password is run the Pre-Upgrade Checker.

vCenter SSL and SSO SSL System Name Mismatch Error:

A common issue that may pop up from the pre-upgrade checker is the warning below talking about an issue with the system name of the vCenter Server certificate and the SSO certificate. As shown below it’s a hard stop and tells you to replace one or the other certificate so that the same system name is used.

If you have a publicly signed SSL Certificate you will need to generate a new cert request and submit that through the public authority of choice. The quickest way to achieve this for me was to generate a new self signed certificate by following the VMwareKB article here. Once that’s been generated you can replace the existing certificate by following a previous post I did using the VMware SSL Certificate Updater Tool.

After all that, in any case I got the warning below saying that the 5.5 SSL Certificates do not meet security requirements, and so new SSL certificates will need to be generated for vCenter Server 6.0.0.

With that, my suggestion would be to generate a temporary self signed certificate for the upgrade and then apply a public certificate after that’s completed.

Ephemeral TCP Port Error:

Once the SSL mismatch error has been sorted you can run the pre-upgrade checker again. Once that completes successfully you move onto the Configure Ports window. I ran into the error shown below that states that the range of port is too large and the system must be reconfigured to use a smaller ephemeral port range before the install can continue.

The fix is presented in the error message so after running netsh.exe int ipv4 set dynamicportrange tcp 49152 16384 you should be ok to hit Next again and continue the upgrade.

Export of 5.x Data:

During the upgrade the 5.5 data is stored in a directory and then migrated to 6.0. You need to ensure that you have enough room on the drive location to cater for your vCenter instance. While I haven’t seen any offical rules around the storage required, I would suggest having enough storage free and the size of your vCenter SQL database data file.

vCenter Upgrade:

Once you have worked through all the upgrade screens you are ready for upgrade. Confirm the settings, take note of the fact that once updated the vCenter will be in evaluation mode, meaning you need to apply a new vCenter 6.x license once completed, check the checkbox that states you have a backup of the vCenter machine and database and you should be good to go.

Depending on the size of you vCenter instance and the speed of your disks the upgrade can take anywhere from 30 to 60 minutes or longer. If at any time the upgrade process fails during the initial export of the 5.5 data a roll back via the installer is possible…however if there is an issue while 6.0 is being installed the likelihood is that you will need to recover from backups.

Post Upgrade Checks:

Apart from making sure that the upgrade has gone through smoothly by ensuring all core vCenter services are up and running, it’s important to check any VMware or third party services that where registered against the vCenter especially given that the SSL Certificate has been replaced a couple of times. Server applications like NSX-v, vCloud Director and vCO explicitly trust SSL certificates so the registration needs to be actioned again. Also if you are running Veeam Backup & Replication you will need to go through the setup process again to accept the new SSL Certificate otherwise your backup jobs will fail.

If everything has gone as expected you will have a functional vCenter 6.0 Update 2 instance and planning can now take place for the 6.5 upgrade and in my case…the migration from Windows to the VCSA.

References:

http://www.vmware.com/resources/compatibility/sim/interop_matrix.php#db&2=998

https://kb.vmware.com/selfservice/microsites/search.do?language=en_US&cmd=displayKC&externalId=1029944

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