For more detailed explanations, scripts and recommendations please follow this link to my article on TechTarget.

It’s tough to leave a good thing. Let’s face it: Exchange 2010 was a solid release. Not only did it bring native support for public folders but it also had direct Remote Procedure Call connections with the option of HTTPS, built-in antispam tools and great third-party support for just about anything we wanted — fax, antivirus and even BlackBerry Enterprise Services.

Unfortunately, Exchange 2010 and the organizations that depend on it are on borrowed time. Microsoft ended mainstream support in early 2015 and extended support is not an option for most of us, so it’s time to start planning an upgrade.

There are well-known compatibility and migration issues that can be solved in advance. With good preparation and planning, Exchange administrators can make the upgrade to Exchange 2013 or 2016 practically invisible to end users. If you follow my list of top five items to handle, then the switch should be fairly painless.

5. Load balancing

Load balancing is not an issue for smaller shops but there are specific differences between Exchange 2010 and later versions that need attention, depending on whether you use F5, NetScaler, or some other hardware or software options.

4. DNS namespaces and certificate planning

What we are really talking about is the names used for Outlook Anywhere (OA), Outlook Web App (OWA), Exchange Control Panel (ECP), ActiveSync (AS), EWS, Offline Address Book (OAB) and Autodiscover. It sounds like a lot but most administrators combine the namespaces for many of these.

3. Third-party compatibility

An organization that relies heavily on a particular add-on should talk to its vendor as soon as possible to see if it can offer a transition plan. Vendors that provide fax, compliance, e-discovery, mobile synchronization or security services, antivirus, backup and recovery, unified messaging and other services do not always have a clear path to newer versions of Exchange.

2. Exchange public folders

I have rated public folders so high because I have seen companies struggle with the transition work in this area for more than a year and severely delay the move from Exchange 2010. The process of moving the folders is cumbersome but even more difficult is the effort needed to identify and determine if a folder and its contents can be removed instead of migrated.

1. Exchange clients

Client software gets top billing in this list. Exchange 2013 and 2016 do not support direct RPC connections for MAPI so you will have to use Outlook 2007 or newer. Also, make sure the Outlook clients are patched.

This is the short list from the entire article but hopefully it helps you with your planning.

Moving your Exchange services to Office 365 seems to be a fairly simple decision for smaller companies; it just makes sense. Most of my larger customers however remain on-prem due to security concerns and higher estimated costs. In addition, there are often political challenges in eliminating local servers and eliminating jobs within IT departments and sometimes irrational fears of a global cloud shutdown or problem. (Blackberry/RIM problems come to mind.)

The slower adoption rate of Office 365 for larger entities is a huge topic and I would need some help in covering that completely, but I did find an interesting article today with price comparisons for small shops. It’s the first time I have seen calculations and a nice chart that shows the costs between the two options for various small company sizes. This article suggests that the price advantage with Office 365 starts to wither once you reach 1,000 mailboxes.

Anyway, check it out.

Comparing Cost for Exchange Online to On Premise for Small to Midsized Businesses