Having been in the enterprise productivity apps game for only three years, Google has made impressive strides with Google Apps, its Web-based messaging and collaboration suite. Since the 2007 introduction, Google has gone from zero to more than 2 million business customers with high-profile examples including Jaguar Land Rover, Motorola, Konica Minolta and fashion conglomerate Roberto Cavalli.Google has also won Google Apps deals with government agencies such as City of Orlando and City of Los Angeles (where all is not rosy) and sold state-wide school district migrations in Maryland, Oregon, Iowa and Colorado.Google Apps' big draw is still price. For $50 per user, per year companies get 25GB of e-mail storage through Gmail along with Google Calendar, Google Talk and Google Groups. Collaboration apps such as Google Docs, Google Sites and Google Video are also included. As part of the deal, Google promises 99.9 percent uptime reliability and 24\/7 customer support with Google Apps.But Google Apps doesn't work for everyone. [ For complete coverage on Microsoft's new Windows 7 operating system -- including hands-on reviews, video tutorials and advice on enterprise rollouts -- see CIO.com's Windows 7 Bible. ]Both Aisle7, a small health and wellness marketing company, and Serena Software, a mid-size maker of change management software, left Microsoft for GAPE (Google Apps Premier Edition) then switched back, choosing Microsoft's more expensive cloud-based service, BPOS (Business Productivity Online Suite).Among the pain points both companies cite: Hits to e-mail productivity and insufficient customer support.1. E-mail Interface QuirksAisle7, a small health and wellness marketing company that provides content for Web sites and in-house kiosks for stores such as Whole Foods and Wal-Mart, moved to Google Apps for its 32 users in early 2009 mostly because of the low price and 25GB of e-mail storage space.Hamstrung by an Exchange server that was failing and costly to manage, Aisle7 needed to save money, says IT manager Jake Harris. Aisle 7's did not want to have Google Apps replace Outlook and Office, but rather complement them.\n\nSlideshow: Windows 7 Hardware in Pictures: The Latest and Greatest Laptops\nSlideshow: Microsoft's Home of the Future: A Visual Tour\nSlideshow: Fighting the Dark Side: Tech's Heroes and Villains\n\n"We quickly realized that the attitude of our users was: 'Take Outlook from my cold dead hands,'" says Harris. "Only 10 people were using Gmail for e-mail initially and within three months it was down to two people. Most did not like how threaded messaging and meeting requests work in Gmail."A big selling point for Aisle7 was Outlook Connector (officially called Google Apps Sync for Microsoft Outlook), a plug-in that synchronizes Outlook e-mail, calendar and contacts with Google Apps. "Google promised that it would have the same feature parity as when you have Exchange on-premise. But neither Outlook Connector nor Gmail worked well."In Gmail, a frequent irritation for Harris was that there is no way to re-send a message (as opposed to forwarding), which can come in handy if you have a regular e-mail that you send out each month. This is something that you can do in Outlook.In Outlook Connector, a problem for Aisle7's users was with meeting requests. One example: If Aisle7 users included an attachment in the meeting request, the invitees would not see the attachment nor would they be able to accept the meeting request, and the organizer wouldn't know there was a problem.Also, if users received a meeting request in Gmail using Google Apps that was sent using Outlook, they could see the date, time and invitees, but could not see notes written in the body of the invite by the organizer.2. User Revolt Redwood City, Calif.-based Serena Software moved to Google Apps in late 2008 for 1,100 users, intending to forsake Outlook and Office and fully use Gmail and Google Docs. That is until a small revolt from users and the legal team, which had issues with how confusing threading can be in Gmail."Once users lose confidence in a tool it's hard to get them back," says Ron Brister, Serena's Director of IT.Users were happy to abandon the Gmail interface for Outlook Connector, but Outlook Connector never worked well, says Brister. "Outlook Connector actually broke a number of times," he adds.Like Aisle7's Harris, Brister takes umbrage with the way distribution lists are set up in Outlook Connector. "With Exchange when you send a group e-mail it populates the "To" field with all members of that group," he says. "In Gmail and Outlook Connector all you see is the e-mail address in the 'To' field. You can't reply to one person or see who's on the list. It's just an http address. You have to reply to all or add people individually and reply that way."Another source of aggravation for Brister was with Gmail's calendar invites. If you add an attachment to a meeting invite the attachment has to be a link to a Google Doc or it won't go through. The solution was to send follow up e-mails to the group with the attachment.3. Downtime HitsIn the one year that Aisle7 was using Google Apps Harris experienced four instances of downtime lasting several hours each, he says, adding that the entire service didn't go down, but some important facets did."Outlook would stop working but IMAP [the e-mail retrieval protocol] would keep working. Or Active Sync protocols would not work but Outlook would work."Aisle7 went live on Microsoft's BPOS service in early June. It was initially interested in the $60 per user per year version that gives full Exchange mailbox functionality with 25GB per user, but decided to invest in the $120 per user per year version, which comes with full Exchange, SharePoint, Office Communicator and Live Meeting.Though more than twice the price of Google Apps Premier, Harris says BPOS will ultimately save the company money because Live Meeting will replace WebEx for Web meetings and video conferencing. WebEx has been costing Aisle7 $600 per user per year.Serena says it experienced slow response times with Google Apps. Eventually one of Brister's IT staffers discovered Serena's data was backed up in a Google data center in Berlin, Germany. "Mountain View is just up the street from our headquarters in Redwood City, so why are we in Berlin?" says Brister. "We issued tickets asking why we're not in a local data center but we had trouble getting any feedback."4. Customer Support LetdownsWhen asked about customer support for Goggle Apps, Aisle7's Harris says: "They hardly offer any. Their policy is unless the service is down you can't call them."Brister says he was nearly driven crazy by what he calls Google's "arrogant and complacent" view of customer service. While most companies will send you slides for new product roadmaps for referencing and ongoing conversations, Google showed Serena its product roadmap via a WebEx online meeting and never actually sent roadmap items or commitments via e-mail, says Brister. "I quickly discovered that nothing ever got achieved. Google just changed the quarter dates on these items, so it was always a sliding scale," he says. "I'd contact them and ask what's the status of such and such? And the Google sales manager would go off the record and say: 'I don't know, looks like it's been delayed.'"Serena has a year left on its Google Apps contract, but is content to walk away because not much money will be lost, Brister says. Though Microsoft is a relative newcomer to cloud services, Brister says he feels comfortable with the BPOS service after a trip to Redmond to see the product roadmap and talk to Microsoft executives.Serena currently has 500 users are still using Gmail and Outlook Connector and about the same amount have moved to BPOS. Brister anticipates an increase in user productivity, more confidence in Outlook, good customer support, and because he tied the BPOS contract in with a new enterprise agreement, he foresees improved license management and compliance."At the very least, we are going back into familiar waters instead of being in deep water without a boat," he says.Shane O'Neill is a senior writer at CIO.com. Follow him on Twitter at twitter.com\/smoneill. Follow everything from CIO.com on Twitter at twitter.com\/CIOonline.