Mid Feb, one of the London VMUG leaders posted on twitter, looking for someone to present on the subject of "upgrading from vSphere 5.5 to vSphere 6.5". This is not a step by step GUI how to guide, but covers the considerations you need to think about.

1. VSPHERE 5.5
THE END (OF SUPPORT) IS NIGH. VSPHERE 6.5 IS CALLING

2. A SMALL BIT ABOUT ME
• Dean Lewis
• Technical Architect Team Leader, Chess ICT
• vExpert, Veeam Vanguard, Cisco Champion
• Blogger – www.educationalcentre.co.uk
• Twitter - @SaintDLE
• This presentation - http://vexpert.me/London-vmug-dean

3. END OF SUPPORT (KB 51491)
• End of General Support for vSphere 5.5 is September 19, 2018
• Includes vCenter 5.5, ESXi 5.5, VSAN 5.5
• In the event you are unable to upgrade before the End of General Support (EOGS) and are active on
Support and Subscription, you have the option to purchase extended support in one year increments
for up to two years beyond the EOGS date.
• Technical Guidance for vSphere 5.5 is available until September 19, 2020 primarily through the self-help
portal.
• During the Technical Guidance phase, VMware does not offer new hardware support, server/client/guest OS
updates, new security patches or bug fixes unless otherwise noted

4. PRODUCTS ALSO AFFECTED
http://www.virten.net/vmware/product-
end-of-support-countdown/

5. VSPHERE 6.5 – NEW FEATURES
• VMFS 6
• 512e and 4K SSDs/NVMe drives support
• Automatic unmap
• Requires creation from new (KB2147824)
• PowerCLI command - Update-VmfsDatastore
• This operation deletes the existing VMFS5 datastore to create a
VMFS6 datastore. You should back up any files from the VMFS5
datastore to prevent any data loss.
• VM level encryption
• Requires a 3rd party external key manager solution
• Common REST API Framework
• vCenter HA
• Predictive DRS (ties into your vRealize Ops Mgr deployment)
• Pro-Active HA
• HTML5 web client built in – updates released into vCenter patches
• vCenter 6.5 for Windows
• Windows 2008 R2 or above
• Database
• Embedded PostgreSQL – 20 Hosts/200 VMs
• External DB for larger (SQL/Oracle)
• Penultimate release
• vCenter 6.5 Appliance (VCSA)
• PhotonOS – developed/Maintained by VMware
• PostgreSQL database that has the scalability of up to
2,000 hosts and 35,000 virtual machines
• vCenter High Availability
• vCenter Server uses the VMware vSphere Update
Manager Extension service

6. OK, LET’S JUST UPGRADE THEN?
Upgrading vSphere includes the following tasks:
1. Read the vSphere release notes.
2. Verify that you have backed up your configuration.
3. If your vSphere system includes VMware solutions or plug-ins, verify that they are compatible with
the vCenter Server or vCenter Server Appliance version to which you are upgrading. See VMware
Product Interoperability Matrix
4. Upgrade vCenter Server. See Overview of the vCenter Server Upgrade Process.
5. If you are using vSphere Update Manager, upgrade it. Refer to the VMware vSphere Update
Manager documentation.
6. Upgrade your ESXi hosts. See Overview of the ESXi Host Upgrade Process.
7. To ensure sufficient disk storage for log files, consider setting up a syslog server for remote
logging. Setting up logging on a remote host is especially important for hosts with limited local
storage. See Required Free Space for System Logging and Configure Syslog on ESXi Hosts.
8. Upgrade your VMs and virtual appliances, manually or by using vSphere Update Manager, to
perform an orchestrated upgrade. See Upgrading Virtual Machines and VMware Tools.

7. THE PLUGINS….
• If your vSphere system includes VMware solutions or plug-ins, verify
that they are compatible with the vCenter Server or vCenter Server
Appliance version to which you are upgrading
• You need to ensure that any VMware based products or 3rd party
applications that tie into vCenter, support the latest versions
• If not, upgrade them first!
• Check VMware KB2147289

8. SSO IS GONE
• Single Sign On has now been migrated into the Platform Services Controller (PSC)
• PSC deals with identity management for administrators and applications that interact with the
vSphere platform.
• Some of the services which are held in the PSC
• VMware License Service VMware Component Manager
• VMware Security Token Service
• VMware Common Logging Service
• VMware Syslog Health Service
• VMware Authentication Framework
• VMware Certificate Service
• VMware Directory Service
• If you need to consolidate your SSO Domains, do this in 5.5 before the upgrade (KB 2033620)
• Enhanced Linked Mode connects multiple vCenter Server systems together by using one or more
Platform Services Controllers.
• Enhanced Linked Mode lets you view and search across all linked vCenter Server systems and replicate roles,
permissions, licenses, policies, and tags.
• Replaces vCenter Linked Mode (which needs to be uninstalled before the migration)

9. UNDERSTAND YOUR TOPOLOGIES
• KB 2147672
• With the replacement of SSO for
PSC, the topologies also change
• During the migration or upgrade
process a mixed environment is
supported.
• 1 single SSO domain
• Multiple SSO sites if needed

10. PRE-UPGRADE TASKS
• Health check the environment
• Check all hardware status
• Check software services (vSphere Web Client, SSO)
• Backup status (Ensure good)
• VMware infrastructure (correct current patch levels, status of VMs, Logging enabled)
• Check your hardware – Compute, Storage, Networking, IO Cards against the VMware Compatibility List
• Read the vSphere upgrade documentation
• https://docs.vmware.com/en/VMware-vSphere/6.5/vsphere-esxi-vcenter-server-65-upgrade-guide.pdf
• Read the upgrade documentation for any VMware Solutions, plugins, 3rd party apps
• Ensure you have your infrastructure details and pre-req configurations in place
• DNS (including any records configured), NTP, Network settings (IP, Subnet, Gateway), Firewall Rules
• Build a Checklist
• Build a table for your software and versions you will upgrade to, include notes/web links
• Detail the upgrade sequence for the various components that need upgrading (order your check list table in this seq.)

11. PRE-UPGRADE TASKS
• Any support tickets (internal or with external support) that are open and cover hardware/services which interact with your VMware
platform, ensure they are resolved first before the upgrade.
• Ensure that you have a backup prior to starting the upgrade process, along with a recovery plan in case you need to revert back.
• Open a support request with VMware Support prior to starting your upgrade process—it will expedite the process should any
issues come up.
• Plan your time accordingly.
• Estimating the time for migration of vCenter Server 5.5 or 6.0 to vCenter Server Appliance 6.5 (KB 2147711)
• Read the vSphere upgrade documentation
• https://docs.vmware.com/en/VMware-vSphere/6.5/vsphere-esxi-vcenter-server-65-upgrade-guide.pdf
• Get familiar with the upgrade process – independent blog post – screenshots
• Windows vCenter 6.5 Upgrade
• Migrating Windows vCenter Server to VCSA 6.5
• vCenter Appliance 6.5 Upgrade

12. THE UPGRADE
• Migrate or Upgrade?
• Migration
• Deploying PSC and vCenter as distributed components
• Upgrade
• Straight upgrade of VCSA (actually deploys a new one) or Windows vCenter
• During the upgrade whilst vCenter is unavailable
• vSphere Distributed Resource Scheduler (DRS) does not work while the upgrade is in progress.
• vSphere HA does work during the upgrade
• vCenter database tips
• Monitor scheduled database jobs to ensure they are running correctly – For more information, refer to KB article: Checking the status of vCenter
Server performance rollup jobs (2012226)
• Collect Stats Rebuild Indexes – For more information, refer to KB article: Rebuilding indexes to improve the performance of SQL Server and Oracle
vCenter Server databases (2009918)
• Delete old data – For more information, refer to KB article: Reducing the size of the vCenter Server database when the rollup scripts take a long time
to run (1007453)
• Locate the cleanup_orphaned_data_MSSQL.sql script in the ISO image and copy it to the Microsoft SQL server.
• Similar for PostgreSQL and Oracle
• https://docs.vmware.com/en/VMware-vSphere/6.5/com.vmware.vsphere.upgrade.doc/GUID-DF67AFB8-6123-4841-89B9-C5A13F09EF3C.html

13. THE UPGRADE
• If using custom SSL certificates, back them up before hand
• Check network connectivity on machine you run the upgrade/migration
from
• DNS lookup and Reverse Lookup
• Basic ping connectivity
• Upgrade the components as per your checklist and sequencing
• Check each component after each upgrade, i.e log into web services, check
health status
• Upgrade your 3rd party products first, likely they will support 5.5 and 6.5 at
the same time.
• Bring your ESXi hosts up to 6.5, remember to use the vendor customized
ISO’s
• Upgrade VMware Tools – remember this is now updated separately to
ESXi releases
• Upgrade virtual hardware version
• Exposes new CPUID features to the VMs (think Spectre/Meltdown patches)
• Ability to use new features such as VM encryption

14. THE UPGRADE
• Upgrade your licensing in https://my.vmware.com
• Install your new licenses – you will currently be on evaluation licenses (60 days)

15. GOTCHAS
• ESXi 5.1 and older cannot be managed by vCenter 6.5
• Devices deprecated and unsupported in ESXi 6.5 (KB 2145810)
• Number of qlogic and Emulex devices that are no longer supported
• End of Availability and End of Support for FCoE on Intel Network Controllers (KB
2147786)
• Microsoft SQL Server Express is not supported for vCenter Server 6.5. The vCenter
Server 5.5 embedded Microsoft SQL Server Express database is replaced with an
embedded PostgreSQL database during the upgrade to vCenter Server 6.5.
• Update manager is now built into the vCenter Appliance – if you have trouble
migrating update manager, uninstall it from your windows machine and don’t
migrate it.
• HP Server - ESXi upgrade to 6.5
• Run the validation first, HP customized installed may have conflicting Mellanox drivers
• Remove using esxcli
• https://nolabnoparty.com/en/esxi-upgrade-from-5-5-to-6-5-conflicting-vibs-with-hpe-
image
• vSphere 6.5 no longer supports the following
processors:
• Intel Xeon 51xx series
• Intel Xeon 30xx series
• Intel core 2 duo 6xxx series
• Intel Xeon 32xx series
• Intel core 2 quad 6xxx series
• Intel Xeon 53xx series
• Intel Xeon 72xx/73xx series

16. GOTCHAS
• VMware is announcing discontinuation of its third party virtual switch (vSwitch) program, and plans to deprecate the
VMware vSphere APIs used by third party switches in the release following vSphere 6.5 Update 1 (KB 2149722)
• Upgrading the VCSA 6.5 to a later version
• Login to the vCenter Server appliance 6.5 VAMI page using the URL (https://vCenter-appliance-name:5480) and login with the
root credentials

17. VSAN CONSIDERATIONS
• vCenter Servers must be upgraded to vSphere 6.5 Update 1 before vSAN hosts are upgraded to vSAN
6.6 or vSAN 6.6.1
• Verify that you have backed up your virtual machines.
• Verify that the software and hardware components, drivers, firmware, and storage I/O controllers that
you plan on using are supported by VMware vSAN for 6.6 and later, and are listed on the VMware vSAN
Compatibility Guide website.
• Verify that you are using the latest patched version of VMware vSAN prior to upgrade.
Please review VMware KB 2146381
https://storagehub.vmware.com/t/vmware-vsan/vsan-6-6-1-upgrade-considerations/vmware-vsan-
upgrade-check-list-2

18. VSAN UPGRADE PATHS
• https://storagehub.vmware.com/t/vmware-
vsan/vsan-6-6-1-upgrade-considerations/supported-
upgrade-paths-for-vsan-6-6-1-1

19. VSHIELD IS GONE, LONG LIVE NSX
• vCloud Network security & vShield Manager are now end of life (19th September 2016), and is not
supported by vCenter 6.5
• Migrate vShield Manager 5.5 to NSX Manager 6.2 (KB 2144620)
• 6.2 is End of General Support – 20th August 2018
• Upgrade NSX Manager to a supported version by vCenter 6.5

20. RESOURCES
• This presentation – http://vexpert.me/London-vmug-dean
• VMware 6.5 upgrade eBook - http://emadyounis.com/upgrade/new-resource-vmware-vsphere-6-5-
upgrade-ebook/
• VMware StorageHub - https://Storagehub.vmware.com
• vSphere Central - https://vspherecentral.vmware.com