What Am I Doing?

Disclaimer: As someone who is still relatively green in the world of IT, I often find myself wading through a labyrinth of technical articles, blogs, and administrator manuals just to keep up with the demands of maintaining an organization’s ever-changing infrastructure. This is my attempt at guiding others who, when faced with a seemingly monumental task, have asked themselves, “What the hell am I doing?”
So They Asked You to Update Exchange…

Part 1: Why Am I Doing This?

In IT, it is crucial to understand, not just the How, but also the Why of what you do. After all, if everything you do is “because my boss/colleague said so”, then that does you no good professionally. The more you understand your infrastructure and what you’re doing, the better able you will be in maintaining and troubleshooting it.
Updating servers is one of those tired maintenance tasks that everyone knows they should do, but only some actually do on a routine cycle (and ideally should be tested prior to production rollout*). The simple reason for these updates is to provide fixes for any known bugs or potential security breaches. Also, in my experience, when requesting support from a vendor, one of the first questions they’ll typically ask is “Are you on the latest update/software/firmware level?”
Exchange is no different and, in fact, is very important to keep up to date for the previously mentioned reasons. In addition, if you have a hybrid on-premises/Exchange Online deployment or if your organization is planning a migration to Exchange Online, then it is required to keep your on-prem Exchange servers at the most recent (or second most recent) Cumulative Update (CU) level to maintain Microsoft support**.

Wait, hybrid deployment? What?

Good question, imaginary voice in my head! There are many different ways to deploy Exchange, but they mostly boil down to three basic topologies: On-Prem (Exchange servers hosted in your organization’s datacenter run all mailboxes/emails services), Hybrid (mailboxes/email services split between on-prem servers and Exchange Online), or Cloud (everything in Exchange Online/O365). Though cloud/Exchange Online has been gaining traction over the past year or so, many organizations are still running on-prem or hybrid deployments***.

So if my company has already migrated to Exchange Online, why should I listen to you?

Because even in a full cloud/Exchange Online deployment, you will likely still have at least one on-prem Exchange server for some basic services**** (typically for DirSync or internal SMTP relay). If you’re one of the lucky few who are purely in the cloud, then I’m incredibly envious of you.
Luckily, the task of maintaining updates for the more recent versions of Exchange (2013/2016) have been made more streamlined through the CU process. Essentially, each CU package is a full install of
Exchange that includes the newest updates and all previous updates. Microsoft has also been religious about releasing these CU packages on a quarterly basis, so expect to see a new CU package every three months.

So, are these “updates” just reinstalling Exchange?

Yep. While it makes the process longer, it also makes it easier since you don’t need to worry about running sequential update chains. And once you’ve run the process a few times, it becomes easier to manage.
Tip: Document your processes and keep those documents up to date! Having a documented process allows others to take care of maintenance tasks if you’re unavailable or to review the process and provide tips/changes to make your life easier. Also, if there’s a persistent issue, then it’s good to have the solution recorded (because otherwise you will forget the next time you’re scheduled to run that maintenance task).
With that said, the first thing you should do to prepare (and this is true for running any major application updates) is to read the release notes for that update level*****…

… No wait, come back!

Seriously, reading the release notes for an application update can save you many hours of headache. These will not only tell you about what’s been fixed in the newest update, but also let you know of any new known issues/bugs. One of the worst experiences I’ve had working in IT was running an update only to have the system crash and fail…and then finding out that it’s a very specific issue that’s already been discovered/documented in the release notes and could have been avoided…
It only takes one night of staying up for 12+ hours straight to learn from your mistakes!

*See: http://www.anexinet.com/blog/importance-patch-testing/
 **Hybrid Deployment Prerequisites: https://technet.microsoft.com/en-us/library/hh534377(v=exchg.150).aspx
 ***Exchange Online Usage as of 2/2016: http://fortune.com/2016/02/01/microsoft-cloud-based-email/
 ****See: https://blogs.msdn.microsoft.com/vilath/2015/05/25/office-365-and-dirsync-why-should-you-have-at-least-one-exchange-server-on-premises/
 *****Release Notes for Exchange 2013/2016: https://technet.microsoft.com/en-us/library/jj907309(v=exchg.150).aspx
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