Major issues – vSphere Upgrade to 5.5 from 5.1

I’m writing this today to have some place to refer back to in order to remind me how painful this process was – and how much I love snapshot technology.

Task: Upgrade Home Lab vCenter 5.1 to vCenter 5.5

Issue: Strange errors that show up during the simple or custom upgrade / install process.


  1. Take a snapshot of vCenter “before 5.5 upgrade”
  2. Run vSphere 5.5 installer –> select Custom Install –> select vCenter SSO
  3. This is where it get fun:
    1. You’ll get a popup that yells at you to make sure your SSL certificate (in my case, default cert) is valid.  (That’s right, the installer doesn’t check this out for you)
    2. Then there is a weird error that it cannot export data.  “There was an error while exporting data.  Installation can continue without migrating existing data.  Do you want to continue.
      1. I decided to look into this.  Turns out this error only applies to an SSO Multi-site environment.  So the installer apparently ASSUMES a multisite environment – poor programming.
      2. Here’s how I figured that out:
        SSO Replication CLI error
      3. In this case, the “unsupported operation” means that it errored out because I don’t have a multisite setup.
    3. At this point the installer proceeded and said it was “successful”.
    4. Now I went to install the web client next.  I got through to this screen when it errored out:
      1. WebClient Error - cannot login to SSO
      2. This was maddening – I checked everything.  I then rebooted and tried again.  No Dice


I’m skipping many troubleshooting steps at this point.  I spent about 5 hours nonstop digging through a dozen (maybe two dozen) articles from VMware site to personal blogs, etc.


At the end of the day, here were the issues I’ve run into:

It appears my upgrade woes are caused by the installer not being able to handle the certificates (self signed in this case) properly.  After I manually uninstalled the SSO and Web Client pieces first, I was met with a different (read much better) result.  See below:

After Manual Uninstall of SSO certificate thumbprint shows

So this is proof positive that the installer is choking on the existing certificates during the upgrade.

Now that the SSO installed properly (remember it did NOT UPGRADE properly) Installer the Web Client Install worked – and note below that the web client is hammering the java.exe piece for about 5 or so minutes (in task manager) – this is good news and to be expected:

Web Client Install successful - java high cpu

Note, now that this installed properly, the Inventory service installed properly and the self signed cert showed up (yay):

Inventory Service Self Signed Cert success

Then I ran into more issues that I just clicked through (boo):

Inventory Service failed to register

Then just when you think it’s looking good when upgrading vCenter:

vCenter Server Self Signed Cert

This happened:

vCenter Server - Could not delete Webservices

Then this:

vCenter Server could not unregister solution user

Once I clicked through all of these and tried to log in to the web client, I got this:

Could not connect to Web Client

Then this:

Web Client Could not retrieve navigation path

I also ran into this issue:
After upgrade, domain administrators, who are part of the local administrators group, cannot log in to vCenter Server In your vSphere 5.1 environment, you gave permissions to the local administrators group, which implicitly includes the domain administrator group. You can log in to vCenter Server 5.1 as a member of the domain administrator group. However, when you upgrade to vSphere 5.5, the domain administrator users no longer have the permissions to log in to vCenter Server. Permissions for local users are maintained after the upgrade.

Workaround: The simplest solution is to log in to vCenter Server as administrator@vsphere.local and to assign permissions directly to the domain administrators group. If other local users who were not inside a subdomain had permissions to manage to vCenter Server users before the upgrade, those users can also log in to vCenter Server and assign permissions to the domain administrators group or any other group.”

So I had to login back in as Local Administrator (changed in 5.5 from admin@System-Domain to administrator@vsphere.local (why this change VMware?):

ESX client - had to add back groups

And for the final horribleness of this upgrade, two of the plugins were failing – I spent about 30 minutes trying to figure out how to get them to work, but gave up:

Plugin Manager plugins not working after upgrade

So at the end of the day, I just “reverted to snapshot” because I was exhausted at how disjointed and cumbersome the upgrade to 5.5 was.  Make sure to let this article sink in at how many issues you’ll come across.  And for the record, this was my home lab – I can’t imagine the egg I would have had on my face if this was a customer production environment.

Incidentally, yes, I’ll be telling my existing customer to “hold off” on the upgrade.  It’s not ready for prime time.

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1 Response to Major issues – vSphere Upgrade to 5.5 from 5.1

  1. Jonathan says:

    I just went to update from 5.1 to 5.5 and once completed (no errors) the database was missing… I was able to login but nothing was was showing! I opted to just revert the Vcenter server and all is better. I will try at a later time and see if I can get it working.

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