vSphere Migration – What I Did (Or Oh No… What Did I Do!?)

A quick post about my recent vSphere Upgrade!

Earlier this month, I began working on a migration project to move production systems from vSphere 5.5 Update 3 to vSphere 6.5. There’s many different reasons I wanted to do so. I’ll be honest, I’m one of the few that actually wanted to get back to the Web Client. At my last job, I used the Web Client exclusively. It’s been really tough to go back to the C# client for the last many months. A few other things? The Content Library and vCenter High Availability are must-haves, in my opinion.

So many options!

Option 1: Upgrade my existing environment to 6.5 with a Windows vCenter and external vCDB

Option 2: Migrate2VCSA – solid, viable choice


Option 3: Fresh environment beside the older environment and manual migration
Option 4: Wait until 5.5 hits End of Life and cry when that day hits
There’s probably a handful more options, but I think these four are likely the most popular (with more than we all care to admit taking Option 4).

Quick Option Breakdown:

In my opinion, Option 1 isn’t all that appealing. VMware has announced the deprecation of Windows vCenter already. On top of that, a distributed deployment of that is a nightmare – no thanks.
Option 2 brings me to the VCSA which has been identified by VMware as the direction which will continue to receive development resources. Added plus is that I can use VCHA with the Appliance. The cons here are that I bring over all of the things that shouldn’t be there. Stale permissions that should be removed or weird vCenter configurations that I haven’t happened upon yet. Not my cup of tea.

Option 3 offered me the ability to do things slowly with more consideration. This is it. This is the one. I was able to set up a new distributed deployment of the PSC and deploy VCHA for the vCenter Appliance. I was able to re-create and organize my Virtual Machine folder hierarchy. I was able to create a better logical design of the virtual infrastructure and use that to guide the migration process.

The best part – it’s all mine! I understand the decisions made. I was able to document permissions and age out stale ones (finding one or two that weren’t, in fact, stale but seldom used). I can say that I know the environment inside and out.

Option 4 was listed as comedic relief, but I’m well aware that there’s some organizations that WILL stay on 5.5U3 right up until it is no longer supported.


A little about the process:

This migration has been a long time in the making. Many months ago I wrote about a script to move DVS port groups to VSS port groups. It was AWESOME to finally see that thing run for its intended purpose. It worked flawlessly!

Essentially, I ran one script to copy all DVS port groups to VSS port groups and flip virtual machine networking. Once I verified network connectivity, I consumed the host in my new environment. Once an entire cluster was in the new environment, I ran another script to create a DVS from VSS port groups. I then manually updated permissions and organized VMs. Were the extra steps? There sure were. Could I have done things a different way? Absolutely! And none of them would have been wrong.

After iterating through all of the clusters, assigning permissions, putting VMs into folders, and allowing some time for the systems to stew I began the upgrade process. The upgrade was the easiest part and another one of the reasons I wanted to use the VCSA – built-in vSphere Update Manager.

In the vExpert Slack and on Twitter, I’ve seen horror stories of VUM in both Windows and VCSA versions. I’ve never had an issue! This time around was no different. The upgrade felt like it was the most time-consuming part of the entire process… host reboots take forever.

Don’t let me fool you – I ran into some issues with the upgrade. Despite hours of testing the process, it just didn’t go perfectly. I beat myself up for it quite a bit, but I learned from it.

I just finished writing a pretty detailed retrospective on the issues I saw when upgrading. I’ll give an overview to those in another post.
How would you have chosen to upgrade? What would you have done to make things easier? What design concepts do you think I missed? Let me know!


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