Moving to the Microsoft Cloud

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black cloudIt’s been said that the devil is in the details.  No truer words were spoken especially when it comes to migrations to the cloud.  In addition, if that migration includes moving your email to the Microsoft Office 365 cloud, you can double down on that statement.  We’ve done a number or Office 365 migrations and have learned all the things that they don’t tell you about migrating to the Microsoft Office 365 cloud.  Here’s a list of things you absolutely must know before you utter the phrase “let’s move it all to the Microsoft cloud”.

Size up your data

Sadly, most failed Office 365 migrations (by failed I mean, outright failure, lost data, missed migration deadlines, or cost overruns) start with the notion that you can simply move all the mail from your server to theirs.  Even the smallest of companies these days has over 250GB of mail data.  If your plan is to suck all of that up into the cloud, you could be talking days to make that happen.  Last I checked, Microsoft doesn’t have a seeding option (move to disk and courier the disk to their data centers).

So the best way to deal with this is to do a massive cleanup of mailboxes (ugh!) or use a tool that allows you to do a pre-migration project to capture all the old mail in the background and do a catch-up transfer later when you are going to go live.  Either way, don’t try this trick at home kids, hire a professional.

Internet bandwidth

If your internet connection resembles two tin cans and a piece of string, don’t even consider it.  You need a reasonably fat pipe to a) move everything without seeding first, and b) have a reasonable experience with your new solution once everything is relocated to the Office 365 cloud.  And you need to remember that upload speeds are every bit as important as the download speeds.  Most cable and DSL providers do not offer synchronous data transfer speeds.  In lay terms, synchronous speeds means the same speed up as it is down.  For example, a major cable provider (not mentioning names but their initials are Shaw Cable) boasts triple digit download speeds but less than 20Mb upload.  Remember: if you are sucking everything up to the cloud, the number that matters is upload.  Don’t even consider a cloud migration of ANY kind until you are happy with your internet.

Mail item limitations

Ever notice how the more mailboxes you open up (including shared mailboxes), the more your email slows down?  Or that once you hit a certain size of mailbox or number of mail items your performance takes a hit?  Think that issue has been resolved by Office 365?  Think again.  Office 365 is Exchange only bigger, after all.  It still has the same issues there as it has here.  Just because it is in the cloud doesn’t change that one iota.  If you couple multiple mailboxes with an oversized Inbox with “two tin cans” bandwidth, be prepared for a big case of lunch-bag letdown.

How do you get around that?  Local archiving is really the only answer – I think I summed this up best with my statement above: Ugh!  Firstly, you will never get your high-income earners to waste their time archiving email (and do you really want to?), so you will be looking for some hired hands to do the heavy lifting (read: time consuming and expensive).  But you’ve got to clean up the crap somehow.

I suppose you could take Microsoft’s suggestion and turn off local caching (meaning working with a live connection to the mailbox instead of a locally cached version) but that will be (far) slower still and will eventually culminate in end-user revolt.  How smart are yseriouslyou going to look when the new solution takes four times as long as the “old solution”, irrespective of how much money you theoretically saved?

Missing data

I can hear the CEO now… “What do you mean I don’t get my Autocomplete addresses, signatures and colour categorized sorting, custom dictionaries and Quick Parts?  I thought you said I’d get everything!”  You respond with “But you got all your emails!”  He is not amused nor placated by that statement, not even close.

Do your homework and figure out what doesn’t actually migrate across (including what I have mentioned above) because you will need a plan for that or you will face the wrath of the aforementioned CEO once he sees what he didn’t get for his money.

What to sync, what not to sync

I already covered email archives.  They are slow and painful and nobody likes them.  Besides, where are you going to store them so they don’t get lost at the most inopportune of moments?  The default is on the local drive!  Who stores data on the local drive?!?!  No one wh has any affinity to said data, that’s for sure!  Now you have to worry about how you are going to backup that archived data because why even archive it if you don’t like it enough to back it up?  Archiving sucks (was that out loud?).

But enough about archiving (did I mention it sucks?).  Even if you have a squeaky-clean Exchange directory – you did get rid of the users who left the company in 2009, right? – there are a ton of service accounts that don’t need to come with you so you need to be selective in what you move across.  No sense in cleaning out your garage AFTER you move, you might as well do that first.

tuberadioBackwards compatibility

Got older apps that integrate with Outlook?  If they don’t support TLS encryption (required by Office 365 for sending emails) you may have problems.  This can be especially true with scanners and multifunction devices (think the Swiss Army knife copier/scanner/printer/fax machine).  There are workarounds but the are kludgy at best.  Youd be best advised to find out prior to migration which hardware and software will make the cut and have a plan for those that don’t.

Metadata and long-file names

Bit of a sidebar here but it bears mentioning.  For those who are also migrating data into SharePoint, you should know that metadata is not guaranteed to make the trip alongside your files.  What is metadata, you ask?  Stuff like file creation dates, modification history, versions etc.  Make sure you keep that in mind when considering compliance or completely avoid the issue by ensuring you have a decent document migration tool – theres lots of them out there.

In terms of long-file names, there was a time when we all lived with the 8.3 file format (8 characters in the name, 3 characters in the extension e.g. number08.no3).  Now we can name files anything we want e.g. nowwecannamefilesanythingwewant.docx.  This is fantastic from a search perspective because we all know that search sucks and any help we can give it using human-recognized mnemonics, the better the chance of finding it when we really need to. The problem is the more long-file names (along with deeply nested folders that are also long), the more chances you will have of the copy crashing out at some point when it comes across something that irritates it.

Who gets what

The last consideration is to make sure you have a deep understanding of who gets access to what.  The best advice we can give here is to clean up and consolidate before you do the move because most of the rights are ALSO not coming over when you migrate.



Need help with an Office 365 migration plan?  We’ve done lots of them and would be happy to help.  Reach out to us today!