Upgrade to ESX 3.5 without leaving your desk
January 31st, 2008 | 
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Is it possible to upgrade to ESX 3.5 without leaving your desk? By downloading the headless upgrade package and using the esxupdate utility with an http depot, absolutely!
I’ve done a handful of upgrades at different companies over the last few weeks without even opening the data center door. One client still has another 15 ESX hosts they will be upgrading in the upcoming weeks that are each at different branch offices. That means that the data center door won’t even be in the same city! The client plans on using the same process for their remaining ESX hosts.
Can you do it too? Probably, but that’s for you to decide based on whether or not your VI3 infrastructure, your blood pressure, and your boss will allow you.
First things first. Get to know the VMware upgrade guide and carefully read the VI3.5 Release Notes. Better yet, ask your favorite VMware Partner to assist you with the planning and implementation, and leverage their training and VMware expertise. Using a Partner will definitely help with your blood pressure and your boss. Now let’s discuss the VI3 infrastructure and the upgrade process.
Upgrade Virtual Center
Did you notice the title of this post is “Upgrade to ESX 3.5″ and not “VI 3.5″ without leaving your desk? If any part of the upgrade is going to make you get up it will be the upgrade to VC2.5. However, Virtual Center can be upgraded via Remote Desktop, and if you plan it out you should be able to stay snug in your cube.
There are some things you need to do first to minimize the potential for problems. If you have not kept your ESX 3.X hosts patched then I recommend you do that first. Check out my previous post about auto patching ESX using an http depot. At a minimum, make sure your hosts are at least updated to ESX 3.0.1 with patch 7557441.
Depending on your current database type (BTW, MSDE has been replaced by SQL 2005 Express) you will need to consider how to migrate. You may not even be concerned about keeping the old data and are willing to start fresh with a new Virtual Center. Whatever your decision, the previously mentioned upgrade guide contains a great section of instructions on migrating and upgrading the various different databases. Mike Laverick over at RTFM also has just published his experiences upgrading, and his .pdf contains pointers to guide you through the same VC rough spots I experienced – with links and screenshots even.
Be sure to plan for your version of VC2. Understand the VI3.5 VMware Compatibilty Matrix
After the VC upgrade make sure your ESX Clusters are working properly and there are no issues with DRS and HA. This was my biggest issue across multiple projects. One client had ESX 3.0.1 hosts that would not connect with VC2.5. I learned about patch 7557441 the hard way, but we still never had to leave the desk. Even my own IT Department’s upgrade was stalled by HA reconfiguration issues, and we had to disable DRS and HA, lose the Resource Pools, and after finally updating all ESX hosts to 3.5 enable DRS and HA again. Unfortunately HA appears to be a constant challenge in all scenarios.
Upgrade your VI client(s)
You can download the new VI Client from the freshly upgraded Virtual Center Web Interface.
VC2.5 is not compatible with the VI Client from previous versions. Once again, review the Compatibility Matrix linked above.
Upgrade ESX Hosts
This section is really why I wrote this post. Up until ESX 3.5, my most common method for doing the upgrades has been to use the installer CD (or download the .iso). Of course, that requires you or someone to put the CD in the ESX host’s CD tray. I never really gave much thought to the other forms of the upgrade binaries available from the downloads page. Specifically, there is the following download option:
Upgrade package from ESX Server 3.0.x to ESX Server 3.5
This package provides expert users with remote, headless upgrade capability from ESX Server 3.0.x to ESX Server 3.5. This package requires the esxupdate utility. Most normal upgrades can be accomplished using the standard CD image.
Downloading the .zip file, extracting it to your http depot, and then pointing the esxupdate tool at the http depot is how you can perform the upgrade without having to be there in person.
Use the following process:
- Assuming you have already created an http depot, download the esx3.5.zip file and extract it to your http depot directory.
- Once you have the code in place you will have to put your host(s) in maintenance mode or shut down VMs before you begin.
- Establish a remote console session to your host with Putty.
- Open the firewall for outgoing http with the following command:
- Run the following esxupdate command:
- The upgraded ESX host will be automatically rebooted at the end of the install process.
- Verify the newly upgraded host reconnects to Virtual Center properly and take it out of maintenance mode.
- Repeat steps 2 through 7 for the next host, and if you have the capacity you can even upgrade multiple hosts at the same time.
Update the VMs
The VMtools will be out of date after the upgrade. You can now select multiple running VMs in the VI Client, right click and choose to upgrade the tools in all VMs selected simultaneously. You will have the option to upgrade the tools interactively or automatically. Interactive upgrades the tools but waits for you to manually reboot the VM. The automatic option installs the tools and reboots the VM for you.
Be sure to upgrade the tools. Bad things could happen if you don’t since the new version of Virtual Center needs to communicate to the latest version of the vmtools.
Summary
The upgrade to VC2.5 and ESX3.5 can be challenging, and maybe even nerve racking, but more often than not you will be able to remotely upgrade your hosts using the upgrade .zip package and a http depot.
OK. So I exaggerated a little. Depending on how many ESX hosts you have you might want to get up from your desk and stretch. Also, as an experienced consultant, I definitely advise you to go to the bathroom as needed. 
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Kevin
