Last week, the City of Boston announced that it was making "a move to the cloud" by adopting Google Apps for all city workers and schools. Google Apps will replace "multiple aging on-premises email systems currently in use"—read: "Exchange Server"—and will even save the city money each year, it's claimed. This is disappointing, and I think that the City of Boston is making a huge mistake.

As you might expect in the wake of such a high-profile loss, Microsoft has come out, guns blazing, offering up a list of several organizations that have made a switch back to Microsoft productivity solutions after having tried Google and failed. This, the company suggests, will happen in Boston as well. More problematically, Google of course has a spotty security and privacy record, Microsoft says.

"We believe the citizens of Boston deserve cloud productivity tools that protect their security and privacy," a Microsoft spokesperson told The Boston Globe. "Google's investments in these areas are inadequate, and they lack the proper protections most organizations require."

I believe that to be true. But a list of the city and state governments that have switched to Google, which was provided by the City of Boston, provides an alarming counterpoint to Microsoft's list. According to the city, government agencies in Los Angeles, Pittsburgh, St. Louis, and the states of Colorado, Maryland, Oregon, Rhode Island, Utah, and Wyoming have all successfully moved to Google Apps. So has the Chicago Public Schools system. (Google claims separately that 5 million businesses use Google Apps, including the U.S. Department of the Interior and Princeton University.)

This is a problem.

According to a Boston Globe article, the City of Boston will spend $800,000 to migrate to Google Apps. But the savings—an estimated $2.50 per employee per month—will save the city about $280,000 a year. (Boston says its current system consists of onsite Microsoft Exchange and Symantec Vault, and costs $8.25 per user per month.)

This notion of "savings" doesn't take into account the issues that city employees will have dealing with the reduced functionality in Google Docs productivity web apps, compared with Microsoft Office. Nor the interoperability issues they'll have sharing documents with outside agencies. This is one of those "gotcha" moments that have derailed other attempted Google migrations, including, I suspect, many of the ones on Microsoft's new list.

I also have to wonder about the real savings that would have occurred had Boston opted for Office 365 instead of Google Apps, retaining the solutions people already understand, as well as document compatibility.

I'm from Boston, and Mayor Tom Menino is sort of infamous in these parts for many things, among them his complete disdain for and ignorance of technology. But the city claims this decision was made by a Technical Evaluation Committee that represented city, police, and school department employees and participated in a "comprehensive selection process" that included proposals from eight qualified providers. (Presumably Microsoft Office 365 was among them.) The city chose a Google Apps for Government and Education partner to provide the cloud services.

Microsoft is also trying to counter the City of Boston news with its own video-based commentary, "Google Docs isn't worth the gamble," which features "Deuce Bigalow" star (maybe that should be written as Deuce Bigalow "star") Rob Schneider as a sleazy casino dealer. More effective, but less humorous perhaps, is a companion blog post that does an excellent job of comparing the Office and Google Apps experiences, and a separate blog post, "Office is a team player," which furthers my comments above about Google Apps–to–Microsoft Office interoperability.

I've written a lot about the back and forth between the Office and Google Apps camps over the past few years, and if you've been following along you might notice some common themes. In 2011, I noted that Microsoft gets businesses and their needs and requirements in ways that Google does not in comparing Office with Google Apps. And in 2012, I argued that Google Apps didn't actually represent much competition to Office 365, despite press reports to the contrary.

Today, I'm starting to see more wins on the Google side, and while I hardly think things have shifted dramatically, it's a concern. Sometimes the threat is overstated. A TechCrunch post that claims Microsoft is "scared" of Google Apps because of—get this—Google's acquisition of QuickOffice is perhaps emblematic of the conversation these days. Scarier, I think, is that Google could fool governments and schools into backing a solution that is so utterly incompatible with the leading document formats and is a potential security and privacy risk. What this boils down to, for me, is that Microsoft is focused on the enterprise and Google isn't. And where Microsoft has done a tremendous job of adapting its on-premises solutions to the cloud, Google doesn't offer the same diversity of solutions.

Sorry, Boston. But you blew it.