As many of you do, I run a vSphere dev environment with instances of Mac OS X and xcode for development. Recently, VMware released an update to their foundation product vSphere updating it from version 5.1 to 5.5. This version fixes a ton of issues with VMware’s poor implementation of Single-Sign On in 5.1, although there are a number of issues one should be aware about as they update.

The most important thing to note is that VMware is phasing out the Windows-based Client used to connect to your environment in lieu of the web-based vCenter access. This seems like a great way to untether VMware from Microsoft (they are also migrating towards using the vCenter Linux-based Appliance), although in the end, Microsoft typically ends up being the operating system virtualized.

The one big issue for me in 5.5 is that if you update your Virtual Machines to use the new hardware version 10, you can no longer change them through the Windows Client and MUST use the vCenter Web interface. Besides not liking this web interface, it creates a critical single point of failure, making it all the more important to provide redundant or heartbeat implementations of vCenter. This isn’t good for me since in 5.1, if vCenter goes down, you can still manage your environment by connecting to each ESXi host independently. You can still do this, but if your VMs are using hardware version 10, you can’t change any of the settings like memory or vCPUs…

Hopefully this gets addressed before VMware finally phases out the Windows client!

Updating vCenter

As with every vSphere environment upgrade, you update vCenter first. Since vCenter is a virtual machine, a quick snapshot before I started saved my butt. Regardless if you use self-signed certificates for SSL or not, when you attempt upgrade vCenter 5.1 to 5.5, you see the following warning:

It’s just a warning, right? Well if you are using self-signed certificates, which most people do in a lab (or even production!), then the upgrade of SSO will fail with the following error.

Action 10:01:43: PostInstallScripts. Importing Lookupservice data…
CustomAction DoUpdateAndMigrateTasks returned actual error code 1603

This issue is documented in KB2060511 and is easily remedied by editing a registry key and deleting a temporary folder. I won’t retype what is in the Knowledge Base, but it helped me work through my vCenter upgrade.

After SSO was installed, the rest installed swimmingly. The first time I connected to vCenter, one of my hosts showed the following error.

Configuration issues. “Quick stats on hostname is not up-to-date”

Once again, VMware KB2061008 to the rescue. In this case, you MUST use the vCenter Web Client to make these changes. So if you are like me, and still use the Windows Client, you really need to start learning the Web Client. I know I am going to make a bigger effort to use it since really, we are going to have no choice soon.

Updating the ESXi Hosts

Now that vCenter is working great, time to update the actual hosts. If you need uptime, make sure you disable automated DRS, host isolation monitoring, and vMotion important VMs that can not go down to other hosts not being updated. If you don’t care about uptime, then there is no need to do rolling updates. Personally I love to use the command-line method for updating. It is clean and simple.

• Upload the depot zip update file from VMware’s download site
• SSH into your host
• Put in maintenance mode
• Run one update command
• Reboot
• Remove from maintenance mode
• Done

As with most things VMware, there is a KB article that covers this procedure. To me, it is by far the easiest unless you are dealing with a sprawling environment with dozens upon hundreds of hosts. In that case, you better learn yourself some VMware Update Manager!

After rebooting my hosts, my OS X VMs no longer started, so I needed to download and run the host unlocker again. There are reported issues with people creating OS X VMs for 10.8 and 10.9, but in my case, my VMs are all OS X 10.7 Lion, then updating to the latest, so I haven’t had any issues yet.

And that is it! Back up and programming again. Please let us know below what experiences you had!

About the Author: Sprawl

Stephen Russell is a Mobile App developer and all around IT geek that spends his days running data centers and his nights coding. This site is the go to place for all of zSprawl's work and the infamous development blog. In his free time, he enjoys tinkering with web code, playing video games, and otherwise plotting to take over the Internets.