Office 365 “The Hard Way”! – What you really need to know about how to migrate your email to the cloud!

If any of you have tried to implement an Office 365 migration one of the first things you will encounter is a complete lack of “decent” documentation from Microsoft.  Especially when it comes to all the “undocumented features” and limitations you will come up against that will have you pulling your hair out by the roots.

Here’s some key points you need to know BEFORE you begin any kind of migration to Office 365.

1. Active Directory integration means sacrificing redundancy and disaster recovery if you are in the SMB market space.  The quick and dirty is that if you want all your usernames and passwords to sync between your AD and Office 365 you have to set up an “active directory connector” which will directly tie your AD to Office 365.  If for any reason your AD on premise goes down, users will NOT be able to use ANY of the Office 365 services.  There is no “independent”  functioning of any of the cloud services if you set up federation between your on premise AD and the Office 365 cloud.  This means that either you will have to invest in redundant architecture (which most SMB’s can’t afford) or you will just have to manage two complete sets of usernames and passwords.  UGH!

2. Office 365’s “Administer on behalf of” feature lacks many of the things you need to set up new users (such as downloading and installing the connector software that actually builds the link between the end users office suite and the cloud exchange/lync servers). Plan on wasting a lot of time having to log in as the business admin or one of the end users to get anything done for setup. Think you can pre-deploy software without logging into EACH individual users account? Think again.  Do it and you end up tying your own partner software licenses to the end users computers and have to go through a lengthy process of uninstalling and re-installing to fix it. And while we are on the subject… I don’t recommend deploying the new Office 2013 suite.  At the time of this writing it is NOT ready for prime time.  I have experienced multiple issues on several different clients, including but not limited to; random crashing, extreme slowness, multiple different plugins breaking, macros no longer functioning, and much more.  NOT FUN! Oh, and don’t even think about installing this on a Terminal Server. Maybe Microsoft will fix these issues in the near future but for now you should stick to Office 2010.

3. There is a major bug involving recurring appointments in Outlooks calendar. BEFORE you sync your calendar with the office 365 cloud you should delete any recurring appointments, otherwise these appointments will not be able to be deleted.

4. If you are using Office 2010 suite (or just Outlook 2010) you must have Service Pack 2 or later installed or Outlook will not connect to the Office 365 Exchange servers.

5. The Exchange portion of Office 365 DOES NOT support any Single mail over 20MB in size. This means if you are doing an Exchange to Office 365 migration you had better plan ahead if your client had their exchange attachment settings allowing even 20MB in total per email.  To help you guys with this problem I have detailed a step by step guide on how I handled this exact problem below:

How to Prepare Your Email Accounts and Mailboxes for Importing Into Office 365

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