One year on: Microsoft Office 365 success remains unclear

Similar complaints have been voiced by some Business Productivity Online Suite (BPOS) customers regarding their move to Office 365. BPOS was aimed at midsized and large companies, and included online versions of SharePoint, Exchange and Lync based on their 2007 editions. It also lacked Office Web Apps, the Office online version. By contrast, Office 365's components are based on the newer 2010 editions of the products.

"Yes, I heard from some smaller businesses I've talked to that Microsoft could have done more to automate the migration process," said Michael Fauscette, an IDC analyst. "Microsoft could have made it easier."

With the recently launched Office 365 for Education, schools and universities that have been using Live@edu will have to engage in a similar transition over the next 18 months or so, so it remains to be seen whether these customers also raise objections to the process.

"You'd hope that Microsoft has learned from the feedback it's gotten about this over the past year now that the Live@edu migrations are starting," Fauscette said.

Because Office 365 was designed to work in hybrid cloud/on-premise environments and to thus be able to interact with on-premises instances of Outlook, SharePoint, Office, Exchange, Lync and other Microsoft products, it often requires on-premises upgrades to desktop and server-side software.

The statistic that more than 90 percent of Office 365 customers are small businesses also raises the question of whether Office 365 has been successful in a different but critical mission: protecting Microsoft's vast installed based of Exchange/SharePoint/Lync/Office on-premises customers as they move to a cloud model for email, productivity apps and collaboration.

"Every CIO in the world is looking at a cloud strategy," Webster said. "Microsoft needs to be able to answer 'Yes' when they ask if Microsoft can help them move to the cloud."

Anecdotal evidence suggests mixed results in this area for Microsoft.