VMWare ESX 4.1 Upgrade to ESXi 5.0 Checklist

I’m starting to plan for an upgrade of VMWare ESX 4.1 U1 to ESXi 5.0 and since ESXi 5.0 makes this possible to do an in place upgrade, I’m hoping things will go smoothly for my environment.

Here’s a checklist/pre-requisite for upgrade.

  • Upgrade vCenter Server (vCenter Server 4 does not support connecting to ESXi 5 hosts)
  • Check the server hardware you are installing ESXi 5 onto is supported and on the VMware HCL.
  • Login to the VMware license portal to check/upgrade/buy your vSphere licenses.
  • Read the ESXi Setup Guide to ensure you understand the pre-requisites.
  • Download the VMware ESXi 5 ISO file from the VMware download area.
  • Burn the ESXi 5 ISO to a CD.
  • Disconnect all Fibre Channel connections (if any) and boot the server from the CD.

Upgrade vCenter Server

Some notes collected from around the ‘net.

Popping Clouds:

  • Don’t use a “!” in your administrator@vsphere.local password. It will cause the SSO installation to roll back.
    • I actually run into this one every time with SSO. For some reason I cannot help but put an exclamation point in the password.
  • When upgrading from 4.1 to 5.x you typically have to pay attention to your SSL certificates. They are (at least in my case) usually expired. In this installation we are using self-signed certificates, so simply renaming the SSL directory in “ProgramDataVMwareVMWare VirtualCenter” to something like “SSL.old” will cause the install to generate new SSL certificates.
  • Make sure you enable certificate validation in vCenter prior to the upgrade from 4.1. Found in the vCenter client under Administration/Server Settings/SSL settings
  • Eject or upgrade any 3.x hosts prior to the upgrade.
  • Make sure that the Microsoft Error Reporting service is set to “Manual.” If it is set to “Disabled” the installation of the SSO components will fail.

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