Upgrade: vSphere 4.1 to 5.5

We have been running vSphere 4.1 Update 2 in production for the past 6+ months, during which time it has been incredibly stable, have had zero issues, go VMWare! Our existing hosts are increasingly running low on memory so in addition to planning their replacement I have also been testing migrating our cluster to 5.5. Our vCenter server is running Server 2008 64bit but unfortunately our database was still stuck on SQL 2005 Express 32bit so this was the first “hurdle” to overcome; would need to do a database upgrade. Our database and ALL vCenter services are running on the same VM, apparently now this is VMWare’s “best practice” as well although I think most of us have been running this way for years!

Depending on the complexity of your environment will depend on how “gruesome” your upgrade path is, I personally think VMWare could have made LARGE portions of this process much more streamlined, perhaps in the future the vCenter Appliance will minimize/eliminate much of this. Our environment is relatively simple in that we have our vCenter server and our hosts, please see this guide if your environment is more complex as there is a STRICT upgrade path that MUST be followed to ensure things go well: http://kb.vmware.com/selfservice/microsites/search.do?language=en_US&cmd=displayKC&externalId=2057795

Luckily our environment uses the KISS theory so our upgrade path is pretty simple:
– Upgrade vCenter Server
– Upgrade ESX hosts (because we are doing a hardware refresh we are just going to install 5.5 on our new hosts and add them to the cluster and then decommission our existing)
– Upgrade VMWare Tools
– Upgrade Datastores

Ok so let’s get started……

First and foremost, PLEASE, spend a ton of time investigating your environment, mapping out what is running, at what code version, etc. You will avoid a lot of issues by ensuring your environment is ready! The VMWare Interoperability Matrix should become your best friend during this process: http://partnerweb.vmware.com/comp_guide2/sim/interop_matrix.php
Also be aware of 3rd party plugins, backup products, etc. as most of these don’t or won’t for a while support 5.5! If you use Veeam for backup like we do STOP RIGHT NOW, not supported yet: http://forums.veeam.com/viewtopic.php?t=17869
UPDATE: Veeam now supports 5.5 see here: http://www.veeam.com/news/veeam-is-first-to-support-both-vsphere-5-5-and-windows-server-2012-r2-hyper-v.html

Upgrade Gotchas

– You MUST make sure your certificates are not expired BEFORE you attempt to upgrade or you will have issues. Please see this KB: http://kb.vmware.com/selfservice/microsites/search.do?cmd=displayKC&docType=kc&docTypeID=DT_KB_1_1&externalId=1009092

– SSL Certificate Checking Must Be Enabled, to enable go to Administration > vCenter Server Settings > SSL Settings > vCenter requires verified host SSL certificates

Run this command on your host to confirm the SSL thumbprint:
openssl x509 -in /etc/vmware/ssl/rui.crt -fingerprint -sha1 -noout

– Remove the Active Directory Lightweight Directory Services role BEFORE upgrading. It seems odd you would have an issue since you already have this installed in your existing environment but you will receive the following error during upgrade if this role exists: Setup cannot create vCenter Server Directory Services. http://kb.vmware.com/selfservice/microsites/search.do?cmd=displayKC&docType=kc&externalId=2006850&sliceId=1&docTypeID=DT_KB_1_1&dialogID=64188928&stateId=1%200%2064206952

– After uninstalling SQL 2005 and installing SQL 2008, I had some “dead” DSN objects, you can manually remove them by going to this registry key:


This is the process I used to upgrade our vCenter Server, including the database portion:

1) TAKE A BACKUP! Personally I shut down our vCenter server, took a snapshot and also did a Veeam Backup just to be safe, if something goes wrong the ability to quickly get back to your starting point is critical!

2) Run Windows Update. Personally I always like to ensure my host is on latest/greatest Windows updates. Also you will need .NET 3.5 SP1 which will be part of Windows Update for the upgrade.

3) After downloading the needed ISOs from VMWare, run the Host Upgrade Checker, it is a quick/simple utility that verifies some basic info. about your environment and can catch some of the basics that may trip up your upgrade. Only takes about 5 minutes or less and spits out a nice “no issues” report for you, its not a guarantee but at least covers some basics. If you don’t have SSL Verification enabled you will get a basic communication error on running the utility.

4) Stop AND Disable all VMWare services. Since SQL Express 2005 does not have an overlapping interoperability with 5.5 we need to upgrade the database and can’t have VMWare trying to use it at the same time, also due to “safety” reboots during the process I elected to disable the services from running as well as a safety net, the upgrade installer will properly reset all these services anyway.

5) Perform a database backup of the VCenter and Update Manager databases, save these to a safe spot for later. Also, make sure you backup your SSL and other info from here:
%allusersprofile%\Application Data\VMware\VMware VirtualCenter

6) Uninstall SQL 2005 Express, client and other utilities. After doing this I elected to do a reboot just to be safe.

7) Install SQL Express 2008 R2 SP2 database, including client and utilities. Again, I elected for a reboot.

8) Create both VCenter and Update Manager databases in 2008, restore the backups you made earlier to these databases using the Overwrite existing options. Also go through and configure permissions for your user/login accounts AND check to make sure SQL services are enabled. Also make sure compatibility is updated to 100 (SQL 2008) otherwise you will have issues if things are running in older SQL compatibility.

9) Create the DSNs for the database. Virtual Center uses a 64bit DSN, Update Manager MUST have a 32bit DSN created. You need to go to the C:\Windows\SysWOW64\odbc32.exe to create a 32bit DSN! Make sure you use the SQL Native 10 Driver when creating these DSNs, if you don’t you will have issues, see here: http://kb.vmware.com/selfservice/microsites/search.do?language=en_US&cmd=displayKC&externalId=1015804

10) Now that you have this done you can run the Simple Install option on the ISO you downloaded, VMWare highly recommends using Simple Install unless your environment has distributed vCenter services or highly complex. Find out more about Simple vs. Custom here: http://blogs.vmware.com/vsphere/2013/09/vcenter-server-5-5-simple-vs-custom-installations.html
During install make sure you choose the necessary options to Keep/Upgrade existing database, etc. At the end you should have a nice shiny install of vCenter 5.5 with all your existing data and of course the vSphere Web Client! Be prepared to do some tweaking with the multitude of new processes running, especially lovely Java as it will eat resources! The upgrade process took around 1 hour or so, 15 mins. or so of this is the database upgrade process running. After running this, go ahead and run the VMWare Update Manager upgrade as well.

At this point you would then be safe to proceed with upgrading your ESX/ESXi hosts, again, check Compatibility guides to ensure you can do a seamless upgrade or just do a fresh install depending on your situation. After upgrading your hosts you can then go through and upgrade VMWare Tools. Because of the inability to edit VMs outside of the vSphere Web Client I would not upgrade to hardware level 10 YET, stay at 9 or lower unless you specifically need version 10. You then also need to upgrade your datastores to VMFS5, because an upgraded datastore is a bit different than a freshly provisioned VMFS5 drive VMWare recommends provisioning new volumes and then storage vMotioning to the new freshly minted VMFS5 volumes instead of upgrading. A bit more info. on this topic can be found here: http://www.derekseaman.com/2013/10/vsphere-5-5-install-pt-3-esxi-upgrade.html


Author: Travis Kensil

Director of IT. Husband and father. Michigan beachbum.

6 thoughts on “Upgrade: vSphere 4.1 to 5.5”

  1. Great Guide Travis. I am in a similar position where I am running the following:
    vCenter 4 + vSphere 4 + 4 x ESX 4.1U3a + Win 2008R2 + SQL Express 2005 32 bit

    I would like to upgrade all above to:
    vCentre 5.5 + vSphere 5.5 + ESXi 5.5 + Win 2012 + SQL 2012

  2. Midway,
    Personally I would wait on 5.5 for a bit. I found have some pretty serious bugs out there that I am waiting on VMWare to fix before we fully commit to upgrade. Perhaps the scariest one is with E1000 NICs causing PSODs on the host, should be getting fixed soon but until then I am not going to move forward. Your mileage may vary though!

  3. I just finished downloading 5.5 software. Nice article here. Going to review some of these things. I have a simple environment as well, just 2 ESX hosts and a dedicated vCenter server on 4.1u2. Enterprise Plus subscription expiring in April so maybe I’ll hold off a little longer before pushing 5.5 out.

  4. We have upgraded vCenter from 4.1 to 5.0 to 5.5 over the past two years. I noticed that all three are still listed in my programs installed. Does anyone know if I can delete the old versions of vCenter and just leave version 5.5 installed?

  5. Travis, your guide is brilliant, thanks so much for sharing. We were in exactly the same position and the above steps saved a lot of headaches.

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