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Tips On Moving to Office 365

There’s no doubt that the Microsoft cloud is becoming more attractive for both enterprise customers and small businesses alike. But taking that initial step can seem daunting, what with a seemingly endless choice of SKU’s to choose from. That choice, however, is critical, as it can affect how many users you support or plan to support.

Remember that with the small business cloud plans you can only have up to 25 users. Now, while this is fine for small companies, you may need to stretch things a little further. The Midsize plan can handle up to 300 users and the Enterprise (E3 & E4) plans can be unlimited. So before you think about migrating to Office 365, select your plan wisely. Full details on all the Office 365 plans can be found at and you can even try Office 365 for a month for free!

If you are looking to migrate to 365, there are a few things to think about. The first thing to consider is which identity provider you are going to choose. The cloud-only option is the simplest, but the chances are that if you're an established business, you will already have Active Directory in one form or another, so the single-sign-on option will probably appeal to you. For this, you'll need an AD forest running on a Windows Server 2008 R2 SP1 (minimum) as well as a friendly little tool called Dirsync (Downloadable via the portal). Don’t let the sceptics frighten you about the dangers of connecting Office 365 to AD, just think of it as a fish on a hook. Yes, you are connecting your AD to Windows Azure, but only through specific attributes. Although it’s important to note that every user must have a valid UPN name (User Principle Name), that’s an email address to you and me.

Recently Microsoft included a new security feature into Dirsync called Password Sync. This nice feature elevates the need complex and expensive ADFS configurations and simply allows passwords to be cached, providing a single sign on. When I say cached, I actually mean that a hash value of the password is generated and then re-generated and it’s this secondary hash value that’s actually used. Thus, no actual passwords are ever compromised. The Microsoft Azure site has a good article about the process: Implement Password Synchronization.

There you have it—just a small taste of Office 365. If you'd like to know more, then join me in September at this year’s IT/Dev Connections Conference in Las Vegas, where you’ll be able to attend my Office 365 Pre-con workshop. It’s a full day, packed with everything you need to know about Office 365, including Identity, Migration, and Hybrid as well as troubleshooting and security. I hope you can make it.


Andy Malone – Microsoft MVP, MCT (UK)

With a prestigious international career spanning 20 years, Andy is not only a world class technology instructor and consultant, but is also a Microsoft Most Valuable Professional and veteran conference speaker at such prestigious events as Microsoft TechEd, IT/Dev Connections, TechMentor-Live 360, and the Cybercrime Security Forum. His passionate style of delivery combined with a sense of fun has become his trademark and have won him great acclaim. 

Although his primary focus is for security, Andy loves to talk about the Windows platform, Exchange , and Office technologies. With knowledge dating back to the MS-DOS 2 and Windows 2.0 era, there is often an interesting story to be told. But technology never sleeps and Andy continues to work with the Microsoft product teams to create and deliver ground breaking material on Azure / Office 365. For 2015, Andy is scheduled to deliver content in Europe and the US and more places. Andy is also about to publish his first book, a Sci-Fi Thriller “The Seventh Day.”

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