A few weeks ago during VMworld 2013 VMware announced vSphere 5.5. We already did a ‘What’s new in vSphere 5.5‘ post but now it is actually available, so it’s time to find out how to upgrade to vSphere 5.5.

But before we start, there are a few caveats:

  • ESXi 5.0 and 5.1 included drivers for network adapters that are not officially supported by VMware, but were very useful for installing ESXi on whitebox hardware. Some of these drivers have been removed, e.g. net-r8168 and net-r8169 for certain Realtek adapters and net-sky2 for Marvell adapters;
  • Once you upgrade a virtual machine’s hardware to VM hardware version 10, it is no longer possible to edit the virtual machine using the traditional vSphere client. Modification to this virtual machine must be executed using the vSphere Web Client. This can be a problem when you are using a free version of ESXi or if you’re unable to manage it through a vCenter server for whatever reason.Hardware version 10.PNG

Because I run a VMware vSphere 5.1 environment, this is a upgrade from vSphere 5.1 to 5.5.
The uupgrade to vSphere 5.5 is a straight forward four step process.

Let’s start the upgrade to vSphere 5.5.


vCenter server upgrade

Step 1: Upgrade the VMware vCenter Server Appliance and, if applicable, the VMware Update Manager. Before you start, check any other VMware associated solution which uses VMware vCenter server, such as VMware View, vCloud Director and Site Recovery Manager. Use the VMware Product Interoperability Matrix to determine which versions of these solutions are compatible with vCenter Server 5.5.

With this version 5.5 VMware removed some of the vCenter Server Appliance limitations. So, when you thought the old vCenter Server Appliance was not suitable for production environments, this one definitely is. vCenter Server Appliance 5.1 with an embedded internal database was limited to a maximum of 5 hosts and 50 virtual machines. With vSphere 5.5 this has been increased with to 100 hosts and 3000 virtual machines. It still lacks the Update Manager and support for vCenter Heartbeat but it’s a huge step in the right (appliance) direction.

Important: Before you start the upgrade process, back-up the vCenter- and Update Manager databases!

When all other solution are compatible and you have created a backup of the databases, it is time to update the vCenter Server Appliance.

This was a first for me  because I’ve always been running Windows based vCenter servers. But with a proper manual it’s actually pretty simple. Simply deploy the new 5.5 version of the vCenter Server Appliance besides your running vCenter Server Appliance. For more information, see Downloading and deploying the vCenter Server Appliance 5.x. The new appliance has a default network configuration, and the vCenter Server service is not configured and disabled, so this doesn’t create a conflict in your environment.

When this is complete, start the new vCenter Server Appliance and connect to both the old and new appliances in a separate browser window using https://ip_address_of_vCenter_VM:5480. In the new appliance, start the vCenter Server Setup wizard, and accept the end user license agreement.


In the new appliance, in the Configure Options panel, select Upgrade from previous version.


In the new appliance, copy the source key.


In the old appliance, go to the Upgrade tab, paste the copied source key and click Import remote key and stop vCenter Server.


This may take a few minutes. When this is done, you will see Import sucesfull. Next, copy the newly generated local appliance key. In the new appliance paste this key in the lower window as the source appliance key.


When you select next, the new appliance and the old configuration are checked for inconsistencies. In my case it encountered a problem with my certificates, so I replaced them.


 Next, provide a new password for the local vCenter Server Appliance Administrator.


When you select next, the Pre-Upgrade checker will check your new appliance and ESXi hosts for inconsistencies.


In my case no errors were detected.


Now you are ready to preform the actual upgrade. Just check the ‘I confirm that I have made a back-up/snapshot‘ message and start the upgrade


After a few minutes the upgrade is complete, just reboot the vCenter Server Appliance and proceed to step 2.


Note: Do not forget to remove the old vCenter Server appliance after you’ve completed the total upgrade process.

 vSphere client upgrade

Step 2: Upgrade the VMware vSphere client which is pretty straightforward. Connect to your new vCenter Server Appliance using your webbrowser, download the vSphere Client and start the installation. Select the correct language.



Select the correct installation location and start the installation.




The first thing you will notice is that the vSphere Client login has changed, it now includes a notification that with vSphere 5.5 all new features are only available in the vSphere Web Client. The legacy vSphere Client will continue to operate but with a vSphere 5.0 feature set. Bye bye legacy vSphere Client, although will will still need it for vSphere Update Manager and Site Recovery Manager but for how long ……


Next, the Web client server installation.

ESX host upgrade

Step 3: Upgrade the ESXi host.

My server is running ESXi 5.1.0, which is eligible for an in-place upgrade to ESXi 5.5.


Now you can do a simple straightforward upgrade using a DVD but what’s the fun in that. Besides that, it’s no problem when upgrading a few hosts but when the number of hosts increases, automate it. If you have to do something more than once, automate it!

We will be using VMware Update Manager to automate the upgrade proces. To do this we will need to create an Upgrade baseline. Now we encounter a small handicap with the vSphere Web Client. With the vSphere Web Client it’s only possible to attach baselines or scan hosts for baseline compliance.


 To create a new baseline we need to fall back on the ‘legacy’ vSphere Client. First we need to import an ESXi image to use in a new baseline. Go to the Update Manager plugin and select tab ESXi Images. Select Import ESXi image and point to the VMware-VMvisor-Installer-5.5.0-1331820.x86_64.iso you downloaded from the VMware website and create a new Upgrade baseline.


We return to the vSphere Web Client to attach the newly created baseline to your ESXi hosts, cluster or datacenter. (Ok, the vSphere Client works just fine, but this is the new way to administer your vSphere environment).


 Now scan your hosts for compliancy. In my case the two servers in my cluster weren’t compliant. So time to upgrade.


 Put the ESXi host you want to upgrade in Maintenance Mode and select Remediate .. If you cannot find the Remediate option, check the ‘legacy’ vSphere Client again, this option is also not available in the vSphere Web Client.


Select the Upgrade Baseline you’ve just created and select the host you want to upgrade.


Here’s a new warning stating that you need to remove incompatible third-party software modules. If you leave the checkbox deselected and remediate hosts that contain third-party modules with the default ESXi 5.5 image, the remediation will fail. If you want to keep using the third-party modules after the upgrade you need to build a custom image that contains the third-party VIBs. You can de this by using the vSphere ESXi Image Builder CLI.

I don’t understand the choice you have here. If you use third-party modules the remediation will fail, so you will need to select the checkbox or cancel the upgrade process and create a custom ESXI image. But no third-party modules in my ESXi hosts, so I can continue.


Last but not least a few very usefull options in larger environment and/or environments using Distibuted Power Management, Fault Tolerance and High Availability. You can configure these cluster features to be disabled during the upgrade process. They will be automatically enable when the upgrade is completed.

Another nice feature is the option to enable parallel remediation of multiple ESXi host in your cluster. Especially when you have a vSphere cluster with much free capacity this is a nice option to speed up the upgrade process.



Now schedule the remediation to start immediately or on a suitable moment.


Choose what you want to do with the virtual machines on the ESXi host you’re about to upgrade. There are three options, ‘Do not change the power state‘, ‘Power of virtual machines‘ or ‘Suspend virtual machines‘.

Another feature is the option to disable any removable media devices connected to the virtual machine on the host. This prevents the upgrade process from failing because one or two virtual machines have ISO-files or DVDs connected to them.


Once the upgrade completes, the ESXi hosts reboots and you will have an upgraded ESXi host. Just move your virtual machines from the other hosts back onto the new ESXi host and repeat the process on the other hosts. It’s also possible to remediate a complete vSphere cluster with one task. The upgrade process will put the ESXi hosts in maintenance mode and vMotion’s the virtual machines to another host.

When you go through all these pages and setting it may look like a lengthy process but it’s actually not. The complete upgrade took me no more than one hour! OK, I have only 2 hosts, when you have more it takes a bit longer but the actual work is in the upgrade of vCenter Server and creating the baseline. When that’s completed it doesn’t matter if you have 2 hosts or 200, Upgrade Manager does all the work for you, upgrading all hosts automatically, putting them in maintenance mode and rebooting them. It’s like a walk in the park!


Next, the Virtual Machine upgrade.

Virtual Machine upgrade

Step 4: The final step in the upgrade process is the upgrade of all virtual machines in the environment. Start the virtual machine upgrade by first upgrading VMware Tools, followed by the upgrade of the Virtual Hardware to version 10. Virtual Machines need to be powered off in order to be upgraded, so you should plan appropriate outage windows for this step. You can perform an orchestrated upgrade of Virtual Machines with vSphere Update Manager, which allows you to upgrade VMware Tools and virtual hardware at the same time.

Warning: Once you upgrade a virtual machine’s hardware to VM hardware version 10, it is no longer possible to edit the virtual machine using the traditional vSphere client. Modification to this virtual machine must be executed using the vSphere Web Client. This can be a problem when you are using a free version of ESXi or if you’re unable to manage it through a vCenter server for whatever reason.Hardware version 10.PNG

Note: vSphere 5.5 fully supports running virtual machines with older versions of VMware Tools as well as Virtual Hardware versions 4, 7, 8 and 9, so you can comfortably run existing virtual machines until a suitable outage window is available. The complete upgrade process is now complete. When you go through all these pages and setting it may look like a lengthy process but it’s actually not. The complete upgrade to vSphere 5.5 took me no more than one hour!

Now you can enjoy all new vSphere 5.5 features VMware has given us/you. Enjoy!