The Niceties
One of the niceties of OS X (since 10.6 Snow Leopard) was its ability to directly connect to a Microsoft Exchange Server (as long as it has service pack 2 or higher.) One of the things I like about Mac Mail is the fact that it is a dedicated app. While Microsoft Outlook isn’t “bad” I find that when I want to look at my mail and my calendar it forces me to switch between the two. Mac Mail and Calendar being separate apps makes this much easier. I like the fact that they address two different work domains and thus two different apps.
The Bug
At my day job I am using 10.9 Mavericks. As Apple makes it quite simple, I was easily able to connect to my employer’s Exchange server. I knew that the “automatic” feature of checking email in Mail’s preferences didn’t work very well for receiving new mail in a timely fashion. So, I simply set it up to poll for new mail about every 3 minutes. I’d set it up similarly before at a previous employer and it had worked quite well. However, I noticed after about an hour, I would stop receiving emails. I could close Mail, then reopen it and I would start receiving mail again.
When opening up the “Activity Window” via the Window->Activity you can see the ongoing operations. What I saw when I stopped receiving mail was that it appeared to be hung while reading mail. The picture to the right what Mail.app looks like when successfully querying Gmail. The stop sign icons allow you to stop requests. Similarly on the hung Exchange Server request I could cancel the current operation and the subsequent requests would work again…for awhile.
No Solution, Yet
It seems this is a known bug and Apple suggests a solution. Their solution is effectively “turn it off and turn it back on agai“. Other suggestions imply it manifests itself in a variety of ways all of which make Mail.app not very useable other than ensuring you are no longer bother by emails (since it will stop checking them). I got so frustrated I have resorted to using Outlook on the Mac.
The forum post suggests that Apple isn’t handling an edge case of authentication negotiations and dropped connections. While Apple might argue “Microsoft isn’t doing it right” it doesn’t matter from the perspective of your users, Apple. Mac Outlook works and older Mail.app on Lion works. If it requires a bit of a hack to fix the issue, then solve the problem of your user’s pain, Apple.
The Intentional Geek 