As 2023 winds down, it’s time to look towards 2024. The beginning of the new year is the perfect time to tackle some of the IT projects you’ve been putting off. Whether it’s an overdue OS upgrade or implementing newer security tools, chances are you’ve already reached the point where the pain of obsolescence is now greater than the pain of making the changes. Delaying the inevitable is only going to make things worse.

As we meet with companies like yours, we’re seeing several commonly delayed upgrade projects. Let’s talk about some of the low hanging fruit with your servers.

Windows Server

One of Windows Server’s strengths is also a weakness. Once you have it configured and running, it’s reliable. So reliable that many companies don’t realize when the version they’re using reaches End of General Support. At that point you either need to pay for extended support or upgrade to a newer version.

The current version is Windows Server 2022, with mainstream support running until 2026. But many companies are still running Windows Server 2019. Mainstream support for that ends in January 2024, which is just a few weeks away. Microsoft does offer extended support after January for a fee. When it comes to the choice between paying to stay on an old product versus paying to move to a new version, the mathematics are clear.

Surprisingly, we sometimes run across companies that are still running even older versions of Windows Server, such as 2016 or 2012. If you have any of these versions in your environment, now is the time to correct that.


Virtual Machines have been a great way to offer flexibility and scalability to your server infrastructure. VMWare ESX is one of the most common tools for deploying and managing virtual machines. As with operating systems, VMWare ESX also has an upgrade cycle you need to keep up with.

VMWare ESX 6.5 and 6.7 were the versions many companies used when moving to virtual machines in the past 10 years. VMware ended support in October 2022, but continued to offer technical guidance until November 2023. Twelve months ago, when support ended, VMWare revealed that 57% of ESX installations were still on 6.5 and 6.7, and 16% were running even older versions! That’s a lot of VMWare installations that need to be upgraded. If you’re still running these older versions of VMWare, by the time you read this VMware’s technical guidance period has ended and you are running your business on an unsupported software tool.

On-premises Exchange Server

Before Office365 was an option, most companies installed Microsoft Exchange on local servers to handle email and other services. As Office365 became available, the thought of replacing already-paid-for software and servers with a subscription service didn’t seem to make financial sense. As time has passed, however, Office365 makes more sense.

On-premises Exchange requires technical expertise to ensure DNS services, firewalls, and ActiveDirectory settings are up-to-date to protect against the latest attacks. You also need to implement redundancy and backup procedures in case anything happens to your local installation. And as your server hardware ages, you’ll incur capital expenses to buy new servers.

That’s why we recommend most companies move to Office365. Redundancy and backups are handled automatically by Microsoft. The service also handles many of the security elements, leaving you with only a few key security options to worry about. Costs are predictable and scale with the number of employees.

Other on-premises installations

Once you move beyond standard office applications, there are plenty of other software tools that don’t run in the cloud like engineering tools or inventory management. When your business depends on these tools, you’ll need to make sure you keep track of the upgrade cycle for each of these. When a major upgrade is due, you’ll also have to decide whether you can upgrade on the existing hardware or not.

Performing an upgrade on existing hardware keeps capital expenses down but requires more planning and testing to avoid business disruption. With the increasing interconnectedness of different software solutions and the complex security requirements, upgrades often end up being more complicated than anticipated. Often this will require phased upgrades, where employees may have to deal with a mixture of old and new software for several days.

In many cases, we recommend a forklift upgrade. With a forklift upgrade, you install new software on new hardware. Software installation and testing can be done on the side while the older installation continues to run your business. Once the new system is fully configured and tested, you basically unplug the old hardware and plug in the new hardware.

Now is the time to plan

As we head into the final weeks of the year, now is the time to perform an inventory and determine if you have any critical software requiring upgrades in 2024. In addition to maintaining support and getting the latest security updates, you’ll also gain access to the latest features and tools to help your business compete effectively. We’ll discuss some of those in the next blog.

The reality is that when critical software reaches end of life, the upgrade decision has already been made for you.

The sooner you start planning, the sooner you’ll benefit from updated software.