Office 365 Transition Potholes

Avoid Obstacles on the Road to Success

Patrick Renzi

It’s a question I get asked just about every time I speak to someone regarding Office 365. What questions should I be asking about the transition? What should I look out for? What is going to happen that I am not expecting? Well that’s the thing: not knowing what to expect makes it awfully hard to plan what to do when it happens. But what if you had a Magic 8-Ball? Something that could warn you of what might happen, before it does. Sadly, such a device doesn’t exist. But where there is no magic, there is Connection – armed with the experts to help you find the answers you’re looking for. Let’s start with some things about Office 365 that may not be completely advertised.

Office 365 Office Apps use a new Microsoft Office package deployment method known as Click-2-Run. Click-2-Run software installs are revolutionary in the way that they are not quite so static. Traditionally, deployed media from Volume Licensing ran as a one-time install. Ever want to load a new Cumulative update, Service Pack, or different edition? This required what was essentially a re-install, with no in-place upgrade. Click-2-Run changes this, offering you the ability to “stream” office effectively and consistently to your users – without any required downtime or updates needed.
Now this probably sounds like a godsend for a busy IT person, and that’s probably because it is. New features and updates are streamed to users without the need to run new installs, without the need to interrupt a user’s day-to-day life. However (as could be assumed considering the title and purpose of this post) there is a catch, a fairly significant one as well. With transitioning into Click-2-Run, Microsoft enabled what I like to call an “error by design”. When deploying any Click-2-Run installs of Office through Office 365 that are of versions 2013 or 2016 (i.e. the two versions available to an Office 365 user), any prior Volume License or perpetual install of an Office Application (Project and Visio are included) will need to be removed from the system. No coexistence is allowed.

Now let’s move onto email, probably the single most popular platform/service hosted through Office 365. One of the main reasons organizations embrace it at the level that they do is because of the redundancy and access afforded them. Cloud email means users can access email on their system regardless of the state of the local domain – and this is absolutely true (!), but once again, there is a catch. Deploying Exchange Online often comes hand in hand with Domain Federation pass-through authentication, enabling what is in all essence Single Sign-On. With a workload as important as email, the last thing you want is a major change to a user’s day-to-day life – something that might have far-reaching consequences (depending on who that user is). That’s why organizations create and enable this Federation Services role. Giving users that Single Sign-On experience that makes their consumption of email that much easier. There is no veiled sarcasm here, this is huge for the majority of the workforce, and so if you knew there was a way to ensure you had it available, wouldn’t you take it? Well, there is obviously, once again, a catch. Enabling Active Directory Federation Services means that for any access to Exchange online through Outlook (even though it is still cloud email) requires an authentication attempt to be sent through your on-premise AD Domain Controller. What this means to you is, you lose access to the local Domain controller and you lose access to your email through Outlook. Now users can still use the Outlook Web App with access to the Internet, but any locally saved .pst files become unusable.

Now I’m not trying to scare you away from Office 365…quite the contrary. I want to quell any uncertainty this new technology may cause. Going to the cloud for tiresome workloads like Exchange shouldn’t be something you have to worry about. It should be celebrated – removing this workload from your system and no longer needing to manage the troublesome storage that comes along with it. But not knowing what to expect can keep you from truly embracing the new technology ahead of us. So for any other questions, please, give an Account Manager a call and ask to speak to a specialist about Office 365, about Azure, or even another cloud provider.