I was so thrilled when I heard that Snow Leopard (AKA Mac OS X 10.6) would support direct integration with Microsoft Exchange! I even went so far as to force our company (and all seven email users) to suffer a migration from MS Exchange 2003 (which doesn’t work with Snow Leopard) to MS Exchange 2007 (I won’t comment about how thrilled I am to upgrade to software that’s already more than two years old). I am the email administrator and am the decider in these matters!

But now my new setup has been working for about a month and reality is setting in. And that reality is that Apple’s Macintosh equivalents of MS Entourage on the Macintosh and MS Outlook on Windows has its own symptoms of old age and bad design! Now the email rage that was focused on Microsoft is pointed right at Apple!

For instance, you can cannot paste into the location field of an appointment iCal on the Macintosh. That’s right: No cut and paste in that particular field! So if you set up a new appointment and you want to have the location handy on your Blackberry or iPhone, you have to type it in separately, which means you have to remember it or write it down on a piece of paper if you don’t have a screen big enough to see both windows at once.

For instance, Macintosh allows you to add an email address as a new record in Address Book, but you can’t specify which “group” that record will be added to (which controls how the record will be synchronized to other databases). So to make sure that the record is synched to Blackberry, Plaxo, LinkedIn, and other databases. you have to remember to go to Address Book and copy the record into the right group!

I can keep for instancing, but the point is that the level of dysfunction with the Apple software promises to meet and potentially exceed the dysfunction of the Microsoft software! And we’re talking about Apple, the company that can do no wrong…

Recently, I have two experiences that have damaged my ability to do business. The first time, Apple Mail failed to send a file with two attachments that totaled about 18MB. With the help of our email hosting service, Intermedia, we tracked it to a known and discussed issue with Apple Mail’s inability to reliably and quickly deliver emails with attachments larger than about 4MB. That instance might have cost us a relationship with a new investor, because it appeared to them that we couldn’t respond in a timely manner. The second time, Apple Mail sent an email that was truncated because the attachments were placed inline in the text of the message rather than appended at the end of the text. That truncated email got sent to our limited partners and caused tremendous confusion about what we were communicating; made us look foolish with our investors.

I am completely committed to Apple’s platforms since I switched to Macintosh (in 2006) and adopted iPhone in addition to Blackberry (2008). I’m even more committed now that I bought the Snow Leopard story about Exchange integration. But I’m wondering whether Apple really does know software as well as it knows hardware and whether it can fix the issues in its software faster than Microsoft.

This entry was posted on Monday, October 26th, 2009 at 1:34 pm and is filed under Technology, Markets. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.