Upgrading VMware Workstation Pro from v15.5.7 to v16: A Comprehensive Guide

As a fellow virtualization geek, I‘m excited to provide you with an in-depth look at upgrading VMware Workstation Pro to the latest version. VMware Workstation Pro continues to be my hypervisor of choice for running multiple operating systems on my Windows desktop.

The recent release of version 16 promises some amazing new enhancements that will be a boon to our virtualization workflows. Let‘s dive right in and see what the new release has to offer, along with a step-by-step guide to upgrade from v15.5.7 smoothly.

Why You Should Upgrade to Version 16

Before we look at how to upgrade, let‘s briefly discuss the benefits of VMware Workstation Pro 16:

• Native Container Support: Docker containers and Kubernetes clusters can now be deployed directly within VMs. This is a huge plus for developing and testing microservices-based applications.

• vSphere 7 Compatibility: You can now remotely manage VMs located on ESXi 7.0 hosts, with support for the latest protocols.

• Expanded OS Coverage: Several new operating systems are now supported, like RHEL 8.2, Debian 10.5, Windows 10 20H2 and more.

• Improved Security: Workstation Pro now integrates with Microsoft‘s hypervisor-protected code integrity for enhanced security within VMs.

Based on my experience, these new capabilities are well worth the upgrade effort. The container support itself is worth the price of admission in my opinion!

Alright, now let‘s get ready to do the upgrade from v15.5.7 to v16.

Step 1 – Checking System Requirements

The first step is making sure your system meets the minimum requirements for VMware Workstation Pro 16, which are:

• 64-bit x86 Intel or AMD processor with 2 cores and 2GB RAM minimum (4 cores recommended)

• 4GB disk space and 4GB RAM (8GB+ recommended for optimal performance)

• Windows 10/11 or Windows Server 2016/2019 host OS

It‘s critical to validate these prerequisites, as an incompatible host will prevent installing v16. I‘d recommend at least 8GB RAM and a 4 core processor for the best experience.

Step 2 – Identifying Your Current Version

Before initiating the upgrade process, you need to confirm which version is already installed. Simply click Help > About VMware Workstation in the menu bar to check.

On my main workstation, this shows I‘m currently on v15.5.7 build-16341506, so I‘m good to proceed.

Step 3 – Backing Up Your VMs

Trust me, you‘ll want to have backups of your critical VMs before doing any major version upgrade. Things can sometimes go wonky with virtualization software upgrades.

I would recommend:

• Taking snapshots of important VMs from within Workstation Pro
• Doing full VM image backups to external drives where feasible

This provides the ability to rollback if something gets borked during the upgrade. Better be safe than sorry!

Step 4 – Download and Install v16

Now we can finally get to the good stuff – actually installing VMware Workstation Pro 16!

Here are the steps:

1. Open VMware Workstation Pro v15.5.7 and select Help > Check for Updates

2. Click the Get More Information button – this opens web page to download v16

3. Login to your My VMware account and accept the EULA

4. Run the downloaded installer executable for v16

5. Accept license agreement and keep clicking Next, until you get to Ready to Upgrade screen

6. Click Upgrade to kick off the upgrade process, which may take a few minutes

7. Finally click Finish when complete to close out the installer

Easy enough! Just be sure to enter your new v16 license key when prompted after re-opening Workstation Pro.

Step 5 – Updating VMware Tools

This is a crucial post-upgrade step. VMware Tools needs to be updated on each of your VMs to match the new version.

Here is the drill:

1. Power on the VM

2. Under the VM menu, select Update VMware Tools

3. Walk through the update wizard prompts

4. Reboot VM when prompted to finish updating VMware Tools

Make sure to do this for ALL your VMs! It prevents driver issues and compatibility headaches.

Step 6 – Migrating Settings from v15

If you want to preserve your existing Workstation Pro configurations, use the Import/Export Settings wizard located under the File menu.

Personally, I find it quicker to just reconfigure things from scratch in the new version though.

Step 7 – Test New Features

The fun part comes next – taking the new features in v16 for a spin!

I would start by deploying a small Kubernetes cluster with some containers in a test VM. Then play around with the cool new vctl command line tool for managing containers.

Review the release notes and documentation to find out what else you can try – like remote vSphere 7 management capabilities.

Troubleshooting Common Upgrade Issues

Despite best efforts, you may hit some speed bumps during the upgrade process:

• Licensing activation failures – this is common after major version upgrades. Try reentering your license key or contact VMware support if activation fails.

• VM compatibility problems – very old VMs may not work properly on v16. Upgrading guest OS if possible often resolves it.

• Networking driver problems – look for v16 compatible drivers, especially for firewalls, VPN clients and other filtering drivers.

Don‘t hesitate to reach out to me for assistance or advice if you run into any problems! I‘ve been through the VMware Workstation upgrade grind multiple times. We‘ll get you back up and running smoothly.

Recommendations for a Seamless Upgrade

Based on upgrading dozens of systems over the years, here are my top tips:

• Test upgrade in a dev environment first whenever feasible
• Gradually roll out the upgrade to groups of users over days/weeks
• Have dedicated support staff available during the cutover period
• Schedule upgrade timing to minimize disruption

Take the time to do it right, and it will pay dividends in the long run.

Closing Thoughts

I hope this guide gives you a good overview of the process and best practices for upgrading VMware Workstation Pro to the latest version. v16 adds some amazing new functionality like Kubernetes support that make it well worth the effort.

Let me know if you have any other questions as you prepare to upgrade! Whether you are a developer, IT pro, or tech enthusiast like me, Workstation Pro remains an indispensable virtualization tool.