Upgrade to vCenter 8 Failing with “Error while configuring vSphere Update Manager firstboot” on Stage 2

Products

• VMware vCenter Server

Issue/Introduction

VCSA is not able to ping during stage 2 of upgrade process 
vCenter is not residing on a standard switch and a static binding dvportgroup 
Firstboot failure during service start

YYYY-MM-DD HH:MM:SS Excption caught in checkException: Register with extension manager
YYYY-MM-DD HH:MM:SS  UpdateMgr received BaseInstallException '{
     "detail": [
         {
             "id": "install.updatemgr.error.extension_reg",
             "translatable": "Failed to register updatemgr extension.",
             "localized": "Failed to register updatemgr extension."

 

Environment

vCenter 7.x
vCenter 8.x

Cause

During the upgrade, vCenter needs to reconfigure with original source IP address and lose access to network during reconfiguration as the VM is residing on a static binding DV Port group. 

 

Resolution

If you are deploying the vCenter Server appliance directly on an ESXi host, non-ephemeral distributed virtual port groups are not supported and are not shown. After the upgrade, you can manually connect the appliance to the original non-ephemeral distributed virtual port group. This is not a limitation when deploying the appliance through a vCenter Server, and you can deploy to ephemeral or non-ephemeral distributed virtual port groups.

Please use the steps in the kb to create an ephemeral portgroup.
Static (non-ephemeral) or ephemeral port binding on a vSphere Distributed Switch