Upgrading Update Manager
Read the following KB article:
Upgrading to vSphere Update Manager 5.5 on a Microsoft Windows platform (2058423)
Upgrade procedure:
Mount the vSphere 5.5 installation media. The installation wizard appears.
In the left pane, under VMware vCenter Support Tools, click vSphere Update Manager and then click Install.

Note: If any of the prerequisites are not met, they are listed in the right pane under Prerequisites.
Select the appropriate language from the dropdown and click OK.
If a previous version of vSphere Update Manager is already installed, the installer displays the message:
An earlier version of VMware vSphere Update Manager is already installed on this computer. Click OK to upgrade to 5.5.0

Click OK.
In the welcome screen, click Next.

Review the End User License Agreement. If you agree, select the I accept the terms in the license agreement option and click Next.
Optionally, select the Download updates from default sources immediately after installation option and click Next.

Note: This option automatically checks for downloading updates. If you want to review the default download sources or configure vSphere Update Manager to use a shared repository, deselect this option.
Enter the vCenter Server URL and a username and password and then click Next.

Notes:
If the Fully Qualified Domain Name (FQDN) or IP address of the vCenter Server and/or the username are not auto-populated, enter the FQDN and/or username manually.
Ensure that the username entered has a minimum of Register extension privilege to be able to register vSphere Update Manager with vCenter Server.
When prompted, enter the database user name and password for the existing database and click Next.

Select one of these options when prompted with a database upgrade warning:

Upgrade existing Update Manager database
Note: You must acknowledge that a backup has been taken of the Update Manager database.
Do not upgrade the existing Update Manager database
Click Next.
Optionally, from the dropdown, select either the IP address or the FQDN of vSphere Update Manager and then, check if the alternative TCP port numbers for the SOAP, Web, and SSL ports of vCenter Server appear and then click Next.

Note from the KB article: These fields are automatically populated with the appropriate URL and port numbers if the service is installed in the current system. The default ports are 8084, 9084, and 9087 respectively. Ensure that vCenter Server and the ESXi/ESX hosts can resolve the vSphere Update Manager.
Note: The next few steps from the Upgrade procedure were not required in my upgrade. The settings from my previous installation were reused including the patch repository location.
Optionally, select the Yes, I have Internet connection and I want to configure proxy settings now option and click Next.
Provide the proxy server address and the proxy server port and then click Next.
Optionally, select the Authenticate proxy using the credentials below option if your proxy server requires authentication and then click Next.
Optionally, provide an alternative installation location and then click Next.
Note: If the current system does not have 120 GB of disk space available, a warning is displayed when you click Next. Click OK to acknowledge the warning.
In the Ready to Install screen, click Install to start the installation.

Installing…
When the installation completes, click Finish.

Installed programs shows the upgraded vCenter Update Manager:

Update Manager Client Plug-in Install
Connect the vSphere Client to a vCenter Server system with which Update Manager is registered.
Select Plug-ins > Manage Plug-ins.
In the Plug-in Manager window, click Download and install for the VMware vSphere Update Manager extension.

If you receive a security warning, click Run.

Choose the appropriate language.

On the Welcome screen, click Next.

Review the End User License Agreement. If you agree, select the I accept the terms in the license agreement option and click Next.
On the Ready to install page, click Install.

If you are prompted by User Access Control, Click Yes.
Installing…
Complete the Update Manager Client installation, and click Finish.

The status for the Update Manager extension is displayed as Enabled.

Click Close to close the Plug-in Manager window.
With vSphere Update Manager upgraded, I can now experiment with upgrading ESXi hosts from 5.1 to 5.5 automatically. There are still a few components left to upgrade, including the vSphere ESXI dump collector, the vSphere Syslog collector and vShere Auto Deploy. More posts to follow!
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