I have a first generation Apple iPhone and on the 11th of July I downloaded the version 2.0 software via iTunes. I had been reading about the iPhone’s new 2.0 software functions and the MobileMe service and was eager to try them out.

We currently have a Microsoft Exchange 2003 infrastructure and I was curious to see how the MobileMe service stacked up against it. I should also mention that we are switching all our infrastructure out for Linux desktops and servers. We already dual boot all of our workstations between Ubuntu and Windows XP Pro. Most computers are now upgraded to VirtualBox on Ubuntu and so we can still use some applications that need Windows.

Although I am comparing MobileMe with Microsoft Exchange Server, I should also point out that we are evaluating other Exchange replacements which are Linux based. On our short list are: Scalix, Zimbra and Open Xchange. So far we seem to be leaning towards Scalix, however Zimbra is also strong in the running.

We are also well into replacing Microsoft Office with Open Office. So far there have not been any problems for us to use all our existing Microsoft Office documents with Open Office. As our preferred email client we have been using Evolution as the replacement for Microsoft Outlook.

So back to the iPhone and MobileMe evaluation.
Since we have a Exchange infrastructure available I first tried setting up a iPhone to connect to the Exchange Server. Even though the iPhone reports that it has connected to our Exchange Server we were unable to get email to or from the iPhone. After looking up Apple’s documentation they indicate a front end server implementation with a ISA server. That’s more infrastructure than we have, and I presume also more infrastructure than most small businesses with Windows Small Business Server Edition setups.
After several unsuccessful attempts I gave up. I did not want to spend a day on this since our Exchange Server’s days are numbered.

So I decided at this point to connect the iPhone to the MobileMe service and try their push technology. Unfortunately this was also unsuccessful and although no errors were reported in the MobileMe control panel applet no contact nor calendar data has been synced to the MobileMe cloud server.

I figured this may be due to the fact that the Microsoft Outlook user profile I used was still connected to the Exchange Server so I created a new Windows XP user profile and a new Microsoft Outlook user profile that did not connect to the Exchange Server. I imported only the contact and calendar data from a PST file backup and did the over ride sync in the advanced preferences in the MobileMe control panel applet.

Voila. I was able to get the contacts to sync to the MobileMe web application. However when I tried to open the calendar on the MobileMe service I got this error:

Calendar Error
MobileMe Calendar could not start because it was unable to load any calendars from the server. Try reloading Calendar. If this problem persists, contact MobileMe Support.

We get this error every time we try to open the calendar in the MobileMe service. I have reported this several times to Apple’s online support, however even though we get a message stating we will receive a reply within 48 hours we have yet to hear back from Apple.

Now all this testing was done from a computer booted into Windows XP Pro. It was time I got to the meat and tested these systems from a Ubuntu Linux system since this is the new infrastructure we are implementing.

The testing on the MobileMe service from Ubuntu turned out to be a very brief experiment. It seems Apple no likey Linux because if you go to the Me.com web site from Firefox 3 on Ubuntu you get this:

mobileme_on_ubuntu_error-sm

I have to say, this is very disappointing. I do not see any reason why MobileMe’s Me.com can work with Firefox 3 on Windows (and presumable Mac) and not on Firefox 3 on Ubuntu. I believe that a browser is a browser and this is contra to the ubiquitous computing holy grail that the technology sector has been preaching for years.

What also surprises me is that I did not hear this anywhere already. You would think that this glaring inoperability would be noted somewhere in the media. It seems that in the shock and awe that has accompanied the iPhone 3G rollout, nobody, including Apple, really tested these systems thoroughly. Clearly the MobileMe service is not ready for prime time. It is very very slow and when you do get it to work it makes your iPhone very laggy because anytime you open your contacts on the iPhone you will be waiting 5 to 15 seconds while it seems to be checking in with the contacts on the cloud Apple servers. This is really unacceptable.

Although not a bug, a feature that is glaringly missing from the MobileMe service is the ability for a organization to use their existing domain name. If Apple wants to attract businesses to this service they will need to be able to use their own branded email addresses instead of the username @ me.com MobileMe service email addresses. Google does provide this capability with their Google Apps platform.

Conclusion

I believe that MobileMe is a really great concept. I expect that the mad rush of iPhone sales has overwhelmed Apple’s expectations and caused for one a serious strain on the servers that run the MobileMe service. I also believe that as Apple treads more and more into Microsoft Windows territory they are learning that no two PC’s are configured the same and this is very different than what you will find in Mac land where the hardware is more similar from machine to machine.

If Apple gets the MobileMe service to run smoother and increase the performance while they fix the initial bugs in the synchronization, they will be providing a terrific infrastructure service at a reasonable price point for small to mid-sized businesses.