How to upgrade Windows vCenter 5.5 to the 6.5 Appliance

In this blog post I will be upgrading (migrating) a Windows vCenter 5.5 deployment to a vCenter Server 6.5 Appliance. VMware vSphere 6.5 finally went general availability on November 15th 2016 (Read GA announcement here). There are many new features and changes in 6.5. The first noticeable change is the thick C# vSphere client is not available with the introduction of the HTML5 vSphere client. Another feature addition is the VCSA now has VMware Update Manager fully integrated. No need for an additional Windows Server to run VUM!

To read more about vSphere 6.5 check out the followings resources:

Before you Start:

  • The migration supports going from 5.5 and 6.0 on Windows to the VCSA 6.5 appliance
  • You will need workstation not counting your Windows vCenter server (in case its physical)
  • Ensure you have the SSO password of your Windows vCenter deployment
  • If you are going to deploy the VCSA on a ESXi server make sure it has a Standard Switch port group that can talk on the same IP as your existing vCenter
  • Take a snapshot of your Windows vCenter VM before the upgrade
  • Rename your Windows vCenter VM with a -old at the end. When you deploy the VCSA you can use the original name
  • If your Windows vCenter is named after the installed version (Example: take a look at the last paragraph in VMware KB 2040354 (Blog post about this coming soon!)
  • Ensure your backup solution and vCenter plugins are compatibility with vCenter 6.5

The migration is a two stage process. The first stage consist of the deployment of the VCSA. The second stage is the migration of the Windows vCenter data to the newly deployed VCSA.


Let’s get started!

On your Windows vCenter Server:

Mount the VMware-VCSA-6.5.ISO and navigate to the migration-assistant folder. In there will be a executable called VMware-Migration-Assistant.exe. Right click and select Run as administrator:

It will launch a window like below. Enter the SSO password. The Migration Assistant window will run through a migration precheck. Once the prompt is at Waiting for migration to start you are ready to switch to your other workstation.

Switch over to your Workstation:

Mount the same VCSA 6.5 .ISO and navigate to the vcsa-ui-installer/win32 folder. Inside there will be an executable named installer.exe, right click and select Run as administrator:

Welcome to the beautiful VCSA 6.5 Installer! Since our goal is a Windows 5.5 migration click the Migrate option:

Welcome to Stage 1! Click Next:

To continue the EULA must be accepted. Click Next:

Enter the information of your existing Windows vCenter server. Click Next:

If you are using the default self signed certificates you will receive the following message. Click Yes:

You can pick between a vCenter or an ESXi host for the appliance deployment target. I’m going to use a ESXi host. Enter your information and click Next:

If the target is using untrusted SSL certificates the following message will appear. Click Yes:

Enter what you want to name the VCSA virtual machine (as it will appear in vCenter inventory) and assign a Root password. Click Next:

Using the chart pick a deployment size that relates to your environment. For my deployment size I am going to select Tiny as its my home lab. Click Next:

Select a datastore for the VCSA to be deployed on.  Click Next:

For best performance do not use the Thin Provisioning checkbox. Since this is my home lab i’ll use it.

Pick a port group and enter a temporary IP address the VCSA can use for the migration. It will only use this IP for the migration and will take over the IP address of the source Windows vCenter server. Click Next:

Look through the Stage 1 Summary, if everything is correct click Finish:

You can monitor the console screens of both the Windows vCenter and the VCSA Installer window. They talk to each other 🙂

You should received a Deployment Complete message. Click Continue:

Note: If you exit the installed you can continue with the appliance setup by using the URL in the message.

Welcome to Stage 2! Where the Windows vCenter data is migrated over. Click Next:

The Installer will perform another pre-migration check. My results show some of the VMware Update Manager baselines and files may not be migrated over. No big deal! Click Close:

The installer will delete the computer account of the Windows vCenter and join itself to your domain. Enter an AD account with this permission and click Next:

Select what data you want to migrate over. I chose to migrate everything by selecting the third option. My vCenter was a recent and hasn’t had much time to collect a large amount of data. Once your selection is made click Next:

You can join the Customer Experience Improvement Program or deselect. Click Next:

Go over the Stage 2 Summary, ensure you have a backup/snapshot of your Windows vCenter, and click Finish:

You must select the check box in order to continue

During the data migration the Windows vCenter will be shutdown and the VCSA will be configured with its IP address. Click OK:

You can monitor the console screens of both the Windows vCenter and the VCSA Installer window. They talk to each other much more during Stage 2!

Stage 2 took the most time by far. Once it completes you should have the below screen with a URL to access the VCSA. Click the link then click Close:

On the VCSA 6.5 landing page you have two URLs, one to the Flash web client and the second to the new HTML5 vSphere Client.

Congratulations! You are now running on the vCenter Server Appliance 6.5!!!

Flash Web Client:

HTML5 vSphere Client:

17 thoughts on “How to upgrade Windows vCenter 5.5 to the 6.5 Appliance

  1. Great post. How would this work if Site Recovery Manager is present? When would you upgrade SRM? Before or after you do the migration from vCenter to VCSA? Thanks!

  2. Hi, I have vCenter 5.5 and SQL Express DB. I want to migrate the DB to our SQL Cluster and upgrade Windows VM from 2008 R2 to 2012 R2. Should I upgrade vCenter to 6.5 BEFORE I migrate the DB into our cluster? Or should I upgrade our current vCenter to 6.5 first then Migrate the DB, then I can create a new VCSA on Windows 2012 R2 and migrate to it?

    Any help would be greatly appreciated!

    • Peter,

      Once you move to VCSA 6.5 (appliance), there is no question of external SQL database. In VCSA appliance, database is internal postgres.

  3. Can you explain your pre-requisite:

    “If you are going to deploy the VCSA on a ESXi server make sure it has a Standard Switch port group that can talk on the same IP as your existing vCenter”

    Is there a particular reason you can’t select a distributed port group?

  4. Thank you very much for your great blog, it relay ease the way how vCenter is being migrated from Windows Platform to an appliance platform. In my case, I have a bit unique setup where I have a dedicated vLAN thats hosts only the Service Console/Management IPs and the vCenter is beside this vLAN too. Any other VMs requires access to the Management vLAN, I configure the Interface to be on the same portgroup.

    Since DNS service is a bit critical in order to manage the whole environment and I’m a person who doesn’t like the ESXi/vCenter to rely on the production DNS/Domain Controllers where the VMs are hosted/running on the same ESXi servers, I have built a DNS service on the same vCenter and all the Records are populated into the DNS zone which is running on the same vCenter.

    Now, during the migration the old vCenter will be shutdown where I have my critical DNS Service is running and all the management infrastructure is relying on this DNS server to resolve the naming/IPs…

    On my production I’m thinking to start by the DNS Service first and start pointing all ESXi/Veeam Backup / vCenter to the new DNS Server and start the migration process… Any other thoughts, most welcome please.


  5. The upgrade Process stopped at 2. Set up target vCenter Server and Start Services 17% for almost 2 hours.
    Starting VMWare Component Manager…

    Its being stuck like this for a while, I just rebooted the VCSA VM and lets see how it goes.


  6. 503 Service Unavailable (Failed to connect to endpoint: [N7Vmacore4Http20NamedPipeServiceSpecE:0x000055ae6a94e6b0] _serverNamespace = / action = Allow _pipeName =/var/run/vmware/vpxd-webserver-pipe)

  7. root@vCenter02 [ ~ ]# service-control –status –all
    applmgmt vmware-cis-license vmware-cm vmware-eam vmware-sca vsphere-client vsph ere-ui
    lwsmd vmafdd vmcad vmdird vmdnsd vmonapi vmware-psc-client vmware-rhttpproxy vm ware-statsmonitor vmware-sts-idmd vmware-stsd vmware-vmon vmware-vpostgres
    pschealth vmcam vmware-content-library vmware-imagebuilder vmware-mbcs vmware-n etdumper vmware-perfcharts vmware-rbd-watchdog vmware-sps vmware-updatemgr vmwar e-vapi-endpoint vmware-vcha vmware-vpxd vmware-vpxd-svcs vmware-vsan-health vmwa re-vsm

  8. Starting all the services which are Stopped manually I managed to access the UI console…

    Service-Control –Start “ServiceName”

    And make sure the Name Resolution from the Machine where you are trying to access the console is able to resolve VCSA appliance.


  9. Hi Guys,
    After couple pf reboots to the vCSA, I noticed some services doesn’t start automatically

    root@vCenter02 [ ~ ]# service-control –status –all
    vmware-content-library vmware-perfcharts
    applmgmt lwsmd pschealth vmafdd vmcad vmdird vmdnsd vmonapi vmware-cis-license vmware-cm vmware-eam vmware-psc-client vmware-rhttpproxy vmware-sca vmware-sps vmware-statsmonitor vmware-sts-idmd vmware-stsd vmware-updatemgr vmware-vapi-endpoint vmware-vmon vmware-vpostgres vmware-vpxd vmware-vpxd-svcs vmware-vsan-health vmware-vsm vsphere-client vsphere-ui
    vmcam vmware-imagebuilder vmware-mbcs vmware-netdumper vmware-rbd-watchdog vmware-vcha

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