So much is written online about the brilliance of Office 365 and why we should move there. I agree with most who say it’s a fantastic way of getting an organization up into the Cloud and to harness the benefits of better connected mobility in an agile business world such as the one now present in the second decade of the twenty first century.

However, while it may be easy to sign up to Office 365, migrating there isn’t exactly straightforward. First, it depends, as many things in the world of technology do, on how many users you’re taking about. I have doubts over the ROI for larger enterprises in using Office 365, but few about small and medium sized businesses utilizing the cloud platform primarily sold for email use.

So the scenario unfolds like this – the business has already got a typical installation using Windows Small Business Server 2003 or 2008 with Exchange 2003 and 2007 respectively. They have approximately 10 real users of this and want to move to Office 365 because – let’s be honest – Outlook Web Access on 2003 and 2007 is pretty dire. The company also wants to benefit from not having to worry about a backup strategy for their burgeoning Exchange environment and want to get rid of the product off their old creaky servers. Fabulous.

Enter the IT guy. He (or she!) is most likely a Microsoft Cloud Partner – this makes sense as it take all of 10 minutes to do so. He sells you the benefits and says he’ll do it over a weekend when things are quiet. He assures you with his devilish charm that you won’t “lose” any emails and that by Monday morning you’ll be back in action, with only a brief outage over the previous weekend. Pretty standard stuff for the tight-budgeted small business of today.

So the IT guy heads off to www.office365.com and signs the company up to the 30-day trial for the P1 plan which serves up to 25 users. Except the trial is limited to 10 users – quite a nasty little surprise to get, but nevertheless, he’s only concerned with 10 users anyway, so off he goes to finish the setup. After a few tricky stages of verifying the domain and updating the DNS records (not pointing them to Office365 because I fail to see why anyone would do that!), he’s ready to go with the weekend migration. Of course, being a devilishly charming IT guy, he already knows that the minimum supported versions of Microsoft Office are 2007 SP2 and upwards, and has cleverly sold the customer brand new Microsoft Office 2010 Home and Business packs (who said the cloud was cheap?!).

So there he is, in the middle of a Friday evening at home logged in remotely (and securely!) into the customer’s PCs and the devilishly charming IT guy is exporting the mailboxes one by one (the quick and dirty method!). Once he finishes, he thinks “I may as well get one guy fully set up with this before I turn in for the night…”, and heads to the Office365 portal. He diligently (after many blank glances at the screen) downloads the Setup tool and proceeds to set up.

But wait, what’s this? Outlook requires some ‘manual steps’ to be set up? Okay, which steps would those be? Damn. Nothing but a whole mess of TechNet notes and some backchatter on the blogosphere. This doesn’t bode well for the devilishly charming IT guy who’s now becoming rather irate and cursing the Redmond WA company who came up with this POS. Okay, calm down – there has to be a way. As with so many things in life today, it’s all about how you search for stuff online. Google is great, but it can’t read minds (yet!) so he tries some different search terms and phrases. Much discussion around manipulating registry keys is discussed, but the problem as he see it is that Outlook cannot be configured because the stupid Exchange 2003 server is trying to be the mack daddy of the organization. The now frustrated and tired IT guy wishes the old BPOS sign-in tool was there to rescue him, but alas, he’s on his own.

Until he remembers what he did before to set up the last customer that went into BPOS who had a tricky configuration. Manually setting up Outlook then becomes the mission. In the absence of steps, the IT guy whacks some details into Outlook only to get nothing back but a rude set of errors about Exchange not being online. Damn. What now? So he checks again for the settings, does some more Google-ing and then finds the answer Microsoft so miserably failed to tell him – make changes to what Microsoft tells you!

Here’s how. First, log into the Office365 portal, then hit on Outlook and wait for the Outlook Web App to load. Then press the help circle on the far right and select the ‘About’ option as here:

Now you’ll see the ‘About’ section which has a whole mess of detail few people really want to see. Your concerned with the ‘hostname’ bit of the setup, and that’s because you need to know what server your Office365 installation (in the cloud) is running on.

Once you have your hostname, you need to make a minor adjustment – adding the word ‘mailbox’ to the equation. So if like above you’re sitting on ‘amsprd0302.outlook.com‘, your Exchange server address is really ‘amsprd0302.mailbox.outlook.com‘. Now, you have pretty much all the detail you need. (Please note: Don’t use these settings as you may not be on this server and any attempt to authenticate will fail.)

Now you need to launch Outlook (2007 SP2 or later) and setup the new profile and account. The devilishly charming IT guy in his wisdom and ridiculous self confidence has of course deleted all the other profiles from the Mail control panel option and of course backed up his NK2 files before doing so – that’s what makes him that little bit special!

So in the Exchange Account Setup for Outlook, your server becomes the one with ‘mailbox’ in it. The username is self explanatory, and it entered in the format of ‘user@domain.com’. Don’t go anywhere just yet though, because you need to head into the ‘More Settings’ options, where you’ll find the secret sauce to this Outlook Anywhere business you so well touted to your business clients when you sold them on the whole ‘cloud’ thing. Head for ‘Connection’ and mark the option box for ‘Connect to Microsoft Exchange using HTTP’ and then select the ‘Exchange Proxy Settings’ box. Now you’ll enter the Exchange server name without the ‘mailbox’ addition and check all the boxes, add in the term ‘msstd:outlook.com’ into the principal name section and change authentication to basic. Now press OK twice, then you can do the ‘Check Name’ thing to see if you hit the jackpot. Of course, you will be prompted for credentials, but hopefully the sign-in tool for Office365 you installed earlier (remember the thing that told you there were ‘manual steps’ to complete – yeah, that!) will keep suppressing future authentication challenges and Outlook will work “just like it normally does” – yeah, the devilishly charming IT guy did promise his customer that assurance, the cocky SOB that he is, and it looks like he’s gonna get away with it too!

All in all, by now you should be connected to the sexy lovable cloud. Now he must do some more dirty tricks like cleaning up NK2 files, importing PSTs and making new signatures – these little tidbits really do go down well with the customer.

Enjoy!