Upgrading vCenter Server 5.1 update 1 to 5.5 in my lab
Part 1

This past summer I had a student in one of my vSphere 5.1 Install, Configure and Manage courses who had attempted an upgrade from an earlier version of vSphere to 5.1 with disastrous results. This fellow was hopping mad and was not impressed by me asking him if he had read the upgrade guides or knowledgebase articles covering the proper sequence and compatibility issues he had encountered.

So with him in mind, I am documenting the process I followed to upgrade my lab vCenter Server and related components to vCenter Server 5.5.

My vCenter system is split between two windows 2008 R2 VMs. The vCenter server, SSO, Inventory service, ESXi Dump collector and vSphere Syslog Collector are on “vc5.mylab.local,” while the vSphere Web Client and vCenter Update Manager are installed on “app-01.mylab.local.” I have another Windows 2008 R2 VM running MS SQL Server 2008 R2 that handles the vCenter and Update Manager databases.

Here are the beginning software versions on my Windows 2008 R2 vCenter VM

In order to avoid the difficulties my former student encountered with a similar upgrade, check out the following before getting started with the upgrade:

VMware Product Interoperability Matrixes

vSphere Upgrade Guide

Best Practices for vCenter Server Upgrades

Required Information for Installing or Upgrading vCenter Single Sign-On, Inventory Service, vCenter Server and the vSphere Web Client — Print this topic and use it as a worksheet for the upgrade and save it for later so you have the answers for the next upgrade!

Update sequence for vSphere 5.5 and its compatible VMware products (2057795)

Upgrade the various products in numerical order.

From the KB article:
Before you update the vCenter Server, disable vCenter Server from vCloud Director. Also ensure that you stop or disable other VMware services so that they do not communicate with vCenter Server during the update process.

In this article I will be running through the upgrade to vCenter Server 5.5 and its related products. The VMware KB article Methods of upgrading to vCenter Server 5.5 (2053130) describes the requirements for upgrading to vCenter 5.5. I will be following the order specified in the section “Upgrading components separately for vCenter server 5.5”:

Upgrade vCenter Single Sign-On.
For more information, see Upgrading to vCenter Single Sign-On 5.5 on a Microsoft Windows platform (2058249).
Upgrade vSphere Web Client.
For more information, see Upgrading to vSphere Web Client 5.5 on a Microsoft Windows platform (2058265).
Upgrade vCenter Inventory Service.
For more information, see Upgrading to vCenter Inventory Service 5.5 on a Microsoft Windows platform (2058272).
Upgrade vCenter Server.
For more information, see Upgrading to vCenter Server 5.5 on a Microsoft Windows platform (2058275).
Upgrade vCenter Update Manager.
For more information, see Upgrading to vSphere Update Manager 5.5 on a Microsoft Windows platform (2058423).

Upgrading vCenter Single Sign-On

Read the KB article below:
Upgrading to vCenter Single Sign-On 5.5 on a Microsoft Windows platform (2058249)

Information Required for vCenter Single Sign-On Installation

Follow the steps outlined in this KB article to back-up the existing 5.1 SSO database:

Backing up and restoring the vCenter Single Sign-On (SSO) 5.1 configuration (2034928) (You will need the “old” SSO admin password for this.) You won’t need the password for the upgrade.

You need to make sure that forward and reverse DNS lookups return the correct information about your SSO server and the vCenter server. See DNS Requirements for vSphere.

Additionally, you need to check the SSL certificate subject name and the registry of the VM running Single Sign-on. In my case SSO and vCenter server are installed on the same VM.

The registry key to check is referenced in this KB article:
Upgrade from vSphere 5.1 to vSphere 5.5 rolls back after importing Lookup Service data (2060511)

Check the HKEY_LOCAL_MACHINE\Software\VMware, Inc.\VMware Infrastructure\SSOServer\FQDNIp registry key value:

If the registry key value is an IP address, this issue might affect your system.
If the registry key value is set to the FQDN value you see in the certificate, your system is not affected by this issue.

The installer will perform a prerequisite check, but it will not stop you from proceeding if the values do not match.

For example:

If there is a mismatch, you need to change the registry value to match the “Subject” name used for the SSL certificate.

Upgrade procedure:

Mount the vSphere 5.5 installation media.

Note: I prefer to browse the install media and launch the “autorun.exe” with the “Run as Administrator.”
If you are prompted by User Account Control, click Yes.

In the left pane, under Custom Install, click Single Sign-On Install and then click Install.

Note: If any of the prerequisites are not met, they are listed in the right pane under Prerequisites.

In the welcome screen, click Next.

If a previous version of vCenter Single Sign-On (SSO) is installed, you see this message in the welcome screen:
An earlier version of vCenter Single Sign-On is already installed on this computer and will be upgraded to vCenter Single Sign-On 5.5.0.

Review the End User License Agreement. If you agree, select the I accept the terms in the license agreement option and then click Next.

Review the Prerequisites check screen and then click Next.

The installer notifies that a previous version is detected and that Users, Groups, Solution Users, and Lookup Service artifacts will be migrated.

Click Next.
vc55upgrade-12

Select a deployment mode and click Next.

vCenter Single Sign-On for your first vCenter Server – Select this option to deploy your first SSO server. This server becomes the first SSO server in a new vSphere authentication domain.

After you select this option:
Provide a password for the SSO administrator user and click Next.

Note from the KB article: This dialog shows information related to a domain by the name vsphere.local. This is not a domain that is auto-detected within the existing environment, but a net new domain used internally by vSphere. The administrator@vsphere.local account performs the same function as the admin@System-Domain account in previous versions of vSphere. For more information about the administrator@vsphere.local account, see the vSphere Software Components section of the vCenter Server and Host Management Guide.

Provide a site name and click Next.

Note: The site name is used in environments where there are SSO servers in multiple sites. Ensure to select this name carefully because it cannot be changed in the vSphere Web Client after the installation completes. “Default-First-Site” is the default site name.

Optionally, provide an alternative installation location and then click Next. (I had previously installed SSO to the “D:” drive on my VM.)