You have four options you first need to consider:

The end of general support for vSphere 5.5 was on September 19, 2018. After you've made sure your environment is backed up and ready for an upgrade, the next step would be deciding what version to upgrade to and what considerations you need to make as part of the support upgrade path.

You have four options you first need to consider:

The first option is to stay on vSphere 5.5 in an unsupported fashion. This wouldn’t be the greatest of decisions, but I do understand that if this is the first time you are hearing of the end of general support, then you may not have the time and resources to make the change and upgrade. Another option may be to explore extended support options with VMware.

The third option could be getting everything to vSphere 6.0, which will be supported until March 12, 2020, so it will give you a few more years before this comes around again. This is the easiest step in terms of time and resources. For more information about this path read this VMware KB article. Don't miss this important information before upgrading to vSphere 6.0 Update 1.

Now we get to the more interesting, and final, option because of the features and functionality that will become available with these next two releases.

vSphere 6.5 and vSphere 6.7 will see you in general support until Nov. 15, 2021. I will touch on some of the functionality you will gain by moving to this platform over the others later on.

vSphere 6.5

vCenter Server Appliance — If you are running a Windows-based VMware Virtual Center today, it might be time to consider this upgrade path since in 6.5, we saw a fully-featured version of the vCenter appliance. The appliance, as you will read later, is the future. It brings concise management, but also scale, ease of migration and the infamous Update Manager that is also embedded into the appliance. VM encryption — Always a bone of contention because with encryption of any data you lose out on something. In vSphere 6.5, you have the ability to encrypt virtual machines at rest, within the hypervisor and at the point the IO comes out of the virtual disk controller. This adds its own benefits alone, but there are more details here. vSAN — This won’t be applicable to all, especially if you are running your shared storage system to provide your VMware datastores where your virtual machines are stored, but a consideration to be made is to look at the capabilities that come with vSAN in the 6.5 release: erasure coding, stretch clustering, QoS, encryption and the list keeps on going. vCenter Management — Introducing the HTML5-based vSphere client. Now this should in no way be the deciding factor on jumping to this version as the HTML5 interface is not complete, and you will find yourself jumping between the interfaces to get things done, but it’s a good step. And as we get to vSphere 6.7, this is the only way to manage your vSphere environment.

vSphere 6.7

The upgrade to 6.7 will depend on many things, including is your hardware compatible with the latest GA version from VMware? A lot has changed on that front, so be sure to check that. vSphere 6.7 was released last year at VMworld 2017 and it had a ton of new and exciting features and functionality that came with it. Amongst the wider offering from VMware, it wasn’t just vSphere; it was the surrounding products also.

Manageability

I mentioned the HTML5 client. Well, in this release, we see things take a much broader step to be the management interface, including not having to jump between multiple windows to perform certain tasks. Another thing to add here is that vSphere 6.7 will be the last version that will support the vCenter Server being on Windows — VCSA all the way.

Storage

A couple of things to note for vSphere 6.7 and the storage scene: When it comes to deciding, the ability to use PMEM (Persistent Memory), which has similar characteristics of memory but retains the data during power cycles, really assists in some of those enterprise applications that just require everything to be faster. There is a whole white paper on this.

The most notable and significant vSAN release came with vSAN 6.7. Firstly, management can be done through the HTML5 interface rather than having to go through CLI and APIs. The vSAN iSCSI supports Windows Server Failover Clusters (WSFC). In 6.5, vSAN already supported modern Windows application layer clustering technologies, such as Microsoft SQL Always-on Availability Groups (AAG), Microsoft Exchange Database Availability Groups (DAG) and Oracle Real Application Clusters (RAC).

There is also the Adaptive Resync feature to ensure a fair share of resources is available for VM I/Os and Resync I/Os during dynamic changes in load on the system.

“vSAN continues to see rapid adoption with more than 10,000 customers and growing. A 600 million dollar run rate was announced for Q4FY2018, and IDC named it the #1 and fastest growing HCI Software Solution.”

Loads more on this can be found here in the What’s New with VMware vSAN 6.7.

There are heaps of other things to consider, but these are just a few things. Also, take a look at the security enhancements and TPM that also landed in vSphere 6.7.

More details on some useful smaller enhancements that could help a decision tree can be found in this VMware article.

How can Veeam help?

Veeam takes vSphere platform support very seriously and has done so since our company’s beginnings. One of the most effective ways that organizations can migrate to a newer vSphere platform is from Veeam replication.

This is a very powerful technique as organizations can migrate workloads to a new cluster with very little downtime and have the ability to fail back if needed. Additionally, this introduces the option of a new cluster. How many times are there things about the old cluster that you would like to change and not move forward to be stuck with forever? Migrating to a new cluster via Veeam replication can allow you to put in new design elements that can be the right choice today. You can find more about Veeam replication in the Veeam Help Center.