vCenter 5.5 Upgrade with Windows Server 2012 R2 – Part 1 – Preparation

This Upgrade Guide details the step-by-step process for upgrading your vCenter Server from 5.1 to 5.5 Update 1c.  Also included is the build of a new Windows Server 2012 R2 OS for the vCenter 5.5 services whilst maintaining a separate SQL Server 2008 R2 Database.

This is an eleven part series, describing how to upgrade from vCenter 5.1 to vCenter 5.5:

I was unfortunate enough to make the decision to deploy the distributed vCenter model in vSphere 5.0, which I maintained through to vSphere 5.1 with SSO 5.1, which has been an operational nightmare to manage.  This post also covers the consolidation of the distributed model to a centralised vCenter setup with an existing, separate Database server.

vSphere 5.1 to 5.5 upgrade

Overview of the process

  • Preparation & Planning
  • Prepare the vSphere Management Cluster
  • Shutdown the existing vCenter services and re-purpose the existing hybrid vCenter/Database server to be a dedicated Database server.
  • Windows Server 2012 R2 server Operating System installation
  • Customise the Windows Server 2012 R2 OS
  • Install the .Net Framework 3.5 Features
  • Install and Configure the 64-bit DSN
  • Import the SSL directory from the original vCenter server
  • Install the vCenter Single Sign-On, vSphere Web Client, Inventory Service and vCenter Server
  • Post Installation Cleanup – including re-integration of Cloud Management Infrastructure (some are covered in this series, but most is out of scope)

Preparation & Planning

  1. This process takes approximately 3 hours.
  2. Download the Binaries for Windows Server 2012 R2, SQL Server 2008 R2 & VMware vCenter 5.5 Update 1c (Build 1945270).  Copy these binaries to a Datastore that is accessible by the Management hosts.
  3. Configure a DRS VM-Host rule that places all vCenter infrastructure on the same Management host, this way you will only need one vSphere Client connection during the upgrade.
  4. Take vSphere Snapshots of all vCenter server infrastructure VMs, including vUM, vC Ops, vIN, vCM, CBM, etc.  This will allow you to roll-back quickly if things go wrong.
  5. Take a full database consistent backup of your vCenter Database server.
  6. Document the RBAC configuration for the entire vCenter hierarchy.  This will be recreated manually.  NOTE: if your vCenter server and SSO service are on the same VM, then the upgrade process will upgrade the service, maintaining the RBAC configuration (see Alternatives heading below).
  7. The SSO 5.1 user “admin@SYSTEM-DOMAIN” has changed to “administrator@vsphere.local” in SSO 5.5.


  • You know what you are doing and have the ability to make changes to vCenter, Active Directory, DNS, etc. (directly or indirectly).
  • You have checked that all of your vCenter plugins and third party services support vSphere 5.5 Update 1c.  You have the necessary procedures for any re-integration tasks.
  • You have a fully functioning vSphere environment with virtual machines running.  No Physical vCenter servers.


  • This process does not migrate the vCenter 5.1 SSO server data to vCenter 5.5.  All permissions will be recreated from scratch.
  • Roll-back – original vSphere infrastructure is a “snapshot restore” away if the upgrade process fails.


Other resources

You can now move to Part 2 of the Configuration Guide.

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Chief Enterprise Architect and Strategist, 4xVCDX#133, NPX#8, DECM-EA.

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