How to easily update your VMware vCenter Server Appliance to VCSA 6.5

Important Update - On Mar 20 2018, VMware VMSA-2018-0004.3 announced that CVE-2017-5715 (Spectre-2) mitigation is now included in the latest patch that you should be using instead of the older patch featured in the original article below. You'll find the newer article here:

• How to easily update your VMware vCenter Server Appliance from 6.5.x to 6.5 Update 1g (VCSA 6.5 U1g) with Spectre mitigation

Article below as it originally appeared.

vCenter Server Appliance 6.5 Release Notes 15 NOV 2016 | Build 4602587

Warning - vCenter/VCSA 6.x should be upgraded to 6.5 before upgrading your host(s) to ESXi 6.5!

Different approaches

The TinkerTry'd method that works reliably in my home lab just isn't ready yet, I'll update this article as time permits. A serious bug, where I'm unable to get a fresh-installed VCSA 6.5 to survive a simple reboot, showing blank inventory in vSphere Web Client and vSphere Client. This is slowing me down a bit, and was already reported here:

• 503 Service Unavailable (Failed to connect to endpoint:

The gist of the new slick upgrade method is that Windows users simply double-click on the downloaded file named:
VMware-VCSA-all-6.5.0-4602587.iso
to mount it as an ISO, then you launch
E:\vcsa-ui-installer\win32\installer.exe
to kick off the wizard style Upgrade routine that looks like the image below.

You can see the complete process with screenshots at

• Upgrade vCenter Server Appliance 6.0 to 6.5
  Nov 18 2016 by Mike Tabor at MikeTabor.com

I can say that it's not quite as simple as it was when we moved from 6.0 to 6.0U2, jump below to the end of the story below to learn why that is. Or have a little fun first.

Here's how we used to do this, when moving up to just a minor point-release:

software-packages install --url --acceptEulas

That method doesn't seem to realize there's major new upgrade to 6.5 out there for the asking:

How about a little creative alteration to the command, adding the --url parameter that allows me to specify the remote repository location at VMware? I've not found anybody else trying this (with good reason, keep reading). Why not give it a go, to see what happens, to learn how VMware has anticipated this sort of silliness:

software-packages install --url https://vapp-updates.vmware.com/vai-catalog/valm/vmw/8d167796-34d5-4899-be0a-6daade4005a3/6.5.0.5100.latest/ --acceptEulas

Nice try, but no go, as it runs the pre-stage.py script, errors out with:
Repository does not contain updates for this product.
as shown below:

You can read all about how it was done so easily before vSphere 6.5, in my original post:

• How to easily update your VMware vCenter Server Appliance to VCSA 6.0 Update 2
  Mar 16 2016

So that's enough tinkering, time to move onward.

It's more of a migrate than an update

Learn more about Photon OS at VMware:

Photon OS™ is a minimal Linux container host, optimized to run on VMware platforms.

and check out the Photon OS wiki at github, and William Lam's Will I get Photon OS when I upgrade my VCSA 5.5/6.0 to VCSA 6.5?, that explains:

VCSA upgrades are "Migration" based upgrades and has been since the very first release of the VCSA in vSphere 5.0.

So we're being moved from SuSE/SLES to Photon OS for this major upgrade, I just haven't tested it all out yet. For now, as always, be sure to back up your VCSA first (NAKIVO or Veeam or many other options), then follow along at:

• Upgrade vCenter Server Appliance 6.0 U2 to 6.5 GA!
  Nov 15 2016 by Jon Kensy at JonKensy.com

Nov 29 2016 Update

This bug, where I'm unable to get a fresh-installed VCSSA 6.5 to survive a simple reboot, is still an issue. What happens is that it installs fine and works great, until VCSA is restarted, along with the ESXi host. All I see is a blank inventory in vSphere Web Client, and in (HTML5) vSphere Client. This is slowing me down a bit, and was already reported here:

• 503 Service Unavailable (Failed to connect to endpoint:

When pointing my browser to the vcsa appliance like this:
https://vcsa
below you'll see the error I sometimes get:

503 Service Unavailable (Failed to connect to endpoint: [N7Vmacore4Http20NamedPipeServiceSpecE:0x00007feeac069480] _serverNamespace = / action = Allow _pipeName =/var/run/vmware/vpxd-webserver-pipe)

Dec 21 2016 Update

I've resolved this VCSA issue, reporting exactly how in the same community post. Yay! This article is now complete.

See also at TinkerTry

• How to easily update your VMware Hypervisor to ESXi 6.5
  Nov 20 2016

• In VMware vSphere 6.5, missing functions in speedy HTML5 Web UI leaves us saddled with vSphere Web Client (Flash), C# Client still connects to hosts, but not to vSphere
  Nov 16 2016

• VMware ESXi 6.5 first look at install/config featuring vSphere Host Client HTML5 Web UI
  Nov 15 2016

• Check out "vSphere 6.5 – Everything You Need To Know" by Brian Graf & "Migrate 2 VCSA (you should)" podcast featuring Emad Younis
  Oct 23 2016

• Order a TinkerTry'd Supermicro SuperServer Bundle - powerful and efficient home virtualization lab solutions

See also

• vCenter Server Appliance (VCSA) 6.5 Installer Improvements
  Nov 15 2016 by Emad Younis

• Upgrade vCenter Server Appliance 6.0 U2 to 6.5 GA!
  Nov 15 2016 by Jon Kensy at JonKensy.com

• Fix your VCSA 6.5 upgrade if it fails with vix error
  Nov 16 2016 by Jon Kensy at JonKensy.com