Upgrading to vCenter Server 5.5 Using a New Server

You may find that you want to start looking at upgrading your vCenter Server to version 5.5 to take advantage of new capabilities, a faster and improved web interface and the ability to upgrade your hosts to ESXi 5.5.


But what if your current server might be for example vCenter 5.1 on Windows 2008R2 with SQL 2005?  You might want to take the opportunity to start clean on more current versions of Windows and/or SQL.  This article is a summary of a process that worked for me as well as a few hurdles encountered along the way.

Before we begin, make sure you also consider the vCenter Server Appliance which is a hardened pre-built vCenter Server running on Linux. Some will desire to run vCenter Server on Windows and if so this post is for you.

This article also assumes SQL is running locally on the vCenter server.  If the database is remote, this article will still work except that either you will not need to move the database, or you’ll be moving it to a different server.

UPDATE:  As this process does not transfer the ADAM database, the existing security roles will NOT be migrated to the new server.  These roles will have to be manually rebuilt unless you want to try some scripts as discussed in this post.  Special thanks to Justin King ( @vCenterGuy ) for pointing out the issue and Frank Büchsel ( @fbuechsel ) for providing the link to scripting permissions import/export! 

Build The New Server

The new server should be Windows 2012 but NOT the R2 version which is not yet supported. If you want to use a local database, go ahead and install the database at this point (we used SQL 2012).

SSL Certificates

We didn’t have custom SSL certificates but you will still need to transfer your SSL certs to work with your existing database.  When I got to installing vCenter Server in a later step I encountered this error and had to go back and grab the certs.

On the current vCenter server you should be able to find the certificates in the following hidden directory:

  • For Windows 2008:
    C:\ProgramData\VMware\VMware VirtualCenter\SSL
  • For Windows 2003:
    C:\Documents and Settings\All Users\Application Data\VMware\VMware VirtualCenter\SSL

Copy everything in the SSL folder and create the following directory on the new server and place them here:

 C:\ProgramData\VMware\VMware VirtualCenter\SSL

For more information see the following KB article on certificate errors related to vCenter Server installation

 Transfer the Database (downtime begins)

Shutdown the vCenter Services so that we can transfer the database.  There’s a few options here.  Our vCenter DB was about 30GB so I simply did a detach and copied the DB files across the wire.  If you have SQL 2008 or later you might want to take a compressed backup or look at a tool like Red Gate or LiteSpeed which can compress your SQL backups into much smaller files to transport. Additionally you also might be able to detach the relevant VMDKs and attach them to the new server, allowing you to copy them at disk speed.

Once you have the database running on the new server we can begin with the vCenter Server install.

 vCenter Server install

First rule here is the use vCenter 5.5A (build 1378901) which fixes some authentication issues on Windows 2012 in some environments.  Second rule is to install the elements one at a time. I prefer to be able to control each install individually and I’ll address each component below.

 vCenter SSO Install

When you install this you have the option to sync with an existing SSO server.  Since the only other server with SSO we were going to retire, I chose the “first server in new site” option.  We will need to edit SSO later on to enable AD authentication but not yet.

 vCenter Web Server Install

When I first installed this component I got a 404 from the web server on each attempt.  As it turns out there is an issue described in this KB article such that the web server will return 404 errors when installed to a drive other than C. Normally I try to install everything I can to a non-C drive, but it seems that this component needs to be on the C drive to function properly.

 vCenter Inventory Server and vCenter Server

These services are mostly straight forward installs.  If you copied the SSL certificates above you should have no issues in this step.  You will have the option to have vCenter automatically attempt to connect to the hosts or to do it manually.  At this point vCenter server should be working, but only local accounts might be able to login.

To fix this login to the web UI for vCenter using either a local account or the SSO admin account and perform the following steps.

1 Browse to Administration > Sign-On and Discovery > Configuration in the vSphere Web Client.
2 On the Identity Sources tab, click the Add Identity Source icon.

Add the appropriate source type such as Active Directory and add it as one of the default domains. For more information see the following help chapter on setting default domains.

vCenter Update Manager (optional)

You should mostly be in business at this point but you may also want to install vCenter Update Manager.  With this step there are a few additional considerations.

First of all you need to create a 32-bit DSN for the Update Manager Database.  There’s a KB article here but I think my method was quicker.  On the 2012 server open up the search charm and type “odbc” and press enter.  You’ll see both the 32 and 64 bit versions of the ODBC configuration utility.  Select the 32-bit utility and create your DSN, but…..

Make sure you use the SQL 2008 R2 Native Driver even if you are using a 2012 database.  As explained in this article, the vCenter Update Manager service will fail to start when using the 2012 Native Client.  Use the 2008 R2 Native Client against the 2012 SQL and it will work fine.

That’s basically it.  To summarize take the following steps:

1)  Build a new 2012 Server (not R2) and install SQL or other database

2) Copy the SSL certificates from the current vCenter to the new server

3) Shut down vCenter Server services

4) take backups and/or snapshots as desired

5) Using the method of your choice, forklift the current vCenter database to the new server (if SQL is local)

6) Install SSO

7) Install vCenter Web Server to the C: drive

8) Install Inventory Manager and then vCenter Server

9) Logon to vSphere with the web UI and configure SSO to authenticate to your Active Directory domains and/or other sources as desired.

10) Manually reconnect to your ESXi hosts if you selected this option

11) Install Update Manager using a 32-bit DSN and the 2008 R2 Native SQL Client.

Now you’ve got vCenter 5.5 using your same database but on a clean Windows 2012 server.  Now you’re ready to take advantage of the new features ranging from the improved web interface, expanded OS support and the ability to update your hosts to ESXi 5.5.  Happy virtualizing!

7 Responses to Upgrading to vCenter Server 5.5 Using a New Server

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  2. Anders O says:

    Hi. Nice write-up. It almost seems too simple. 🙂

    How about the server name of the Windows machine? I don’t see anything about changing it, so I assume you kept the new name and a new IP address. Wouldn’t this mess up anything, such as the ESXi hosts not finding the new vCenter Server?

    Since my customer is running distributed switches, I’m extra worried about disconnections and outages.


  3. Erick says:

    Great article, got a few questions: what version of vcenter server did you migrate from (I’m planning to migrate from 5.0)?
    Step 10: what’s the procedure to connect the hosts attached to the old vcenter? For example: did you have to dissasociate the esxi hosts from the old vcenter prior to?

  4. Robert says:

    really good article,

    i have the same question as erick. What if i have a new dns name for the vcenter and a new ip adresse. Did i need to disconnect the hosts from the old vcenter prior i stop the vcenter service?

  5. Brad says:


    It’s generally best practice to create a DNS alias for your virtual center server to use in the installation. That way when you upgrade the hardware down the road you can simply point the DNS alias to the new IP address.

  6. Edwart says:

    DNS Alias? Can you explain it please.
    I want to know about the new name of server and the new IP, Will be any problems?

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