At the time of writing, there are 197 days left before vSphere 5.5 is end of life and no longer supported. I am currently in the middle of an architecture project at work and was reminded of the importance of upgrading — not just for the coolest new features, but for the business value in doing so.

Last year at VMworld, I had the pleasure of presenting a session with the indomitable Melissa Palmer entitled “Upgrading to vSphere 6.5 – the VCDX Way.” We approached the question of upgrading by using architectural principles rather than clicking ‘next’ all willy-nilly.

Planning Your Upgrade

When it comes to business justification, simply saying “it’s awesome” or “latest and greatest” simply does not cut it.

Better justification is:

• Extended lifecycle
• Compatibility (must upgrade to ESXi 6.5 for VSAN 6.5+)
• vCenter Server HA to ensure RTO is met for all infrastructure components
• VM encryption to meet XYZ compliance

It is important to approach the challenge of a large-scale upgrade using a distinct methodology. Every architect has their own take on methodology, it is unique and personal to the individual but it should be repeatable. I recommend planning the upgrade project end-to-end before beginning the implementation. That includes an initial assessment (to determine new business requirements and compliance to existing requirements) as well as a post-upgrade validation (to ensure functionality and that all requirements are being met).

There are many ways to achieve a current state analysis, such as using vRealize Operations Manager, the vSphere Optimization Assessment, VMware {code} vCheck for vSphere, etc.

I tend to work through any design by walking through the conceptual model, logical design, and then physical. If you are unfamiliar with these concepts, please take a look at this post.

An example to demonstrate:

• Conceptual –
  • Requirement: All virtual infrastructure components should be highly available.
• Logical –
  • Design Decision: Management should be separate from production workloads.
• Physical –
  • Design Decision: vCenter Server HA will be used and exist within the Management cluster.

However, keep in mind that this is not a journey that you may embark on solo. It is important to include members of various teams, such as networking, storage, security, etc.

Future State Design

It is important to use the current state analysis to identify the flaws in the current design or improvements that may be made. How can upgrading allow you to solve these problems? Consider the design and use of new features or products. Not every single new feature will be applicable to your current infrastructure. Keep in mind that everything is a trade off – improving security may lead to a decrease in availability or manageability.

When is it time to re-architect the infrastructure versus re-hosting?

• Re-host – to move from one infrastructure platform to another
• Re-architect – to redesign, make fundamental design changes

Re-hosting is effectively “lifting-and-shifting” your VMs to a newer vSphere version. I tend to lean toward re-architecting as I view upgrades as an opportunity to revisit the architecture and make improvements. I have often found myself working in a data center and wondering “why the hell did someone design and implement storage/networking/etc. that way?” Upgrades can be the time to fix it. This option may prove to be more expensive, but, it can also be the most beneficial. Now is a good time to examine the operational cost of continuing with old architectures.

Ensure to determine key success criteria before beginning the upgrade process. Doing a proof of concept for new features may prove business value. For example, if you have a test or dev cluster, perhaps upgrade it to the newest version and demo using whatever new feature to determine relevance and functionality.

Example Upgrade Plans

Rather than rehashing examples of upgrading, embedded is a copy of our slides from VMworld which contain two examples of upgrading:

• Upgrading from vSphere 5.5 to vSphere 6.5 with NSX, vRA, and vROPs
• Upgrading from vSphere 6.0 to vSphere 6.5 with VSAN and Horizon

These are intended to be examples to guide you through a methodology rather than something that should be copied exactly.

Happy upgrading!