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The first step I took in migrating to Office 365 was to move over my e-mail to Exchange.  This was certainly the hardest part to get working the way I want, and the area where I encountered the most Microsoft strangeness…

Domain Names

When I first created a fee Office 365 Small Business Premium Trial account it set me up to use e-mail at  Once I decided to move everything over to Office 365 I clearly wanted e-mail to my normal address to arrive in my Exchange Account.  Office 365 Admin makes it easy to port in a domain or modify your own DNS settings, and I elected to do the latter as I am quite happy with my current domain and Web hosting.  The instructions online on the Office 365 site were great, although I did things a little bit differently to de-risk the migration.

I wanted to do a seamless switchover to Office 365, so I wanted to set everything up without actually changing my MX records until I was completely ready.  Office 365 won’t let you set up mailboxes until it has checked you own the domain, but that can be done by adding a simple TXT record to the domain – which doesn’t change an mail routings.

I also found out that to connect a mail client it is important to set up the autodiscover entry on DNS.  Again, this doesn’t change mail routings but does allow mail clients to find the account automatically – which is much easier than using manual settings.

This done, I was able to set up the correct users, and change the MX record at my leisure.

Copying Content

One I had created the mail account, I was able to log into it using Outlook.  From Outlook it was then a case of simply “drag and dropping” all my contacts, calendars and my mail archives into the appropriate place on the new account, then sitting back while it all synchronised with exchange.

If you are going down the Office 365 route and your mail isn’t already in Outlook (e.g. it’s on Google Mail) then I’d strongly recommend connecting Outlook to the current mail account temporarily to manage the transition.

Once Exchange had synchronised completely, I was able to see all my mail, contacts and calendars in the “Outlook Web App” on the Office 365 web site.

Avoiding WINMAIL.DAT and Other Horrors

One of the well known problems with Exchange mail is that it likes to use some of its own mail formats.  If messages in these formats get sent out to non-outlook users, then they often either see only the plaintext version or an un-openable “WINMAIL.DAT” attachment.  The Charity I am a director for recently transitioned to Exchange, and this problem bugged them for months.  I was determined not to fall foul of it and embarrass myself with clients and friends!

There are a few different reasons that WINMAIL.DAT gets sent, and each needs a different approach

  • Exchange thinks its a good idea (for reasons of its own. best not explored)
  • A contact is flagged to receive mail in “Rich Text” format (which Outlook may have decided for reasons of it’s own, also best not explored)
    • The best way to overcome this is to invest €20 in this tool:
    • Open it up from the new tab it installs in Outlook and configure it as follows
      • Processing Tab: All Contacts in Outlook
      • Settings Tab: Tick “All” next to “Field(s)”, then select “InternetFormat” and set the “Overwrite” box to “Autodetect”
      • Press the go button (two gears and a green arrow)

Once I had carried out both of these steps, my testing showed NO further WINMAIL.DAT problems.

Forwarding Mail

In the Office 365 control panel it’s easy to add extra addresses for a user, so for example “” is an additional address for my account, and mail comes to me.  What isn’t so obvious is how to forward mail to accounts outside the Office 365 instance.  In fact, this isn’t possible from the Office 365 admin pages at all – but it can be done from the Exchange Admin Pages – which aren’t linked.  Should you need to get there, you have to find the URL and type it in manually:

Once there, the process is still not that intuitive:

  • Select “Recipients” on the left menu, then “Contacts” from the tabs
  • Add a “Mail User” with the “External E-mail address” you want mail to be forwarded to, and the “User ID” set to the address you want to forward

Android E-Mail- Missing Folders

Once everything was up and running I connected the Android mail client (on my Samsung Galaxy Note 2) to Exchange.  Once I did some of my folders were missing.  These were all folders that have been in use for years, so they may have been created in the late 1990’s, and for some reason they weren’t showing up.  The only solution I found was to rename the folder in Outlook to “My Folder OLD”, create a new “My Folder”, move all the contents of “My Folder OLD” to it then delete “My Folder Old”.  It tool about 20 minutes but completely resolved the problem.

Android Calendar – Uneditable Entries

I also had a problem with the calendar on Android – there were some appointments I couldn’t edit.  It turns out that because these had been created pre-migration with a different Outlook user name, Android was a bit confused and wouldn’t let me edit them.  I could have manually recreated all these appointments, but instead I have just lived with it – it’s a very small number of appointments that I created a long time ago and would need to edit now.  When I do encounter the situation, I just create a new appointment on my phone and delete the duplicate if it’s bothering me in the desktop version.


It was a bit of a learning journey dealing with the issues listed above during the migration, but the result is excellent.  Calendar, contacts and e-mail are now completely and seamlessly available in Outlook, on my phone, and in Office 365 online.  The offline working and synchronisation is completely seamless and needs no attention, and working with iffy data connections on the train is no problem.  Brilliant.


* This list of commands worked for me, and was cobbled together with information from:

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