As an Exchange Admin, I frequently am called upon to troubleshoot rather odd calendaring behavior. Usually, the culprit is mixing of client types (something Microsoft recommends avoiding) or synchronization issues involving cached-mode Outlook or Exchange Web Services clients such as Apple Mail or Outlook:mac misbehaving. But, through it all, I frequently find myself wondering “Why do all of these folks run into these problems? I never do.”

I can’t say that any more.

Last week, I was out one day, and, per the procedure of our group, I placed a note about it on our group’s shared out-of-office calendar, using Outlook Web App to place the item directly on that shared mailbox’s calendar. Today, I received a message from my manager asking me to put my absence on the OOO calendar. Which I had already done. But he sent me a screen grab from his Outlook:mac client showing that it did not appear for him.

“Well,” I thought. “Maybe his Outlook:mac client isn’t properly syncing with the calendar.”  I opened up the calendar in Outlook (which I always run in online mode, never cached mode.) Sure enough, there it was. But then I noticed something else. My absence was the only item I could see on the calendar for that day, but the screen capture that my manager had sent included an item for HIS absence on that day. Which wasn’t showing on my view via Outlook. Furthermore, when I opened my item in Outlook, I was listed as the only attendee. The OOO mailbox was not. Yet this was an item on the OOO calendar and not on mine. That really shouldn’t happen.

Then the plot thickened. Since I have Full Access permission on the OOO mailbox, I fired up OWA and used the  “Open Other Mailbox” feature to open the OOO mailbox, and moseyed over to the calendar on the date in question.  There was my manager’s item. Mine wasn’t there.

I had my co-worker Doug take a look, just to make sure I wasn’t crazy. After all, I’m running on about 4 hours of sleep this morning, and I could have easily been misinterpreting what I was seeing. But I wasn’t.

Okay. The next logical course of action was to delete the item and re-create it. This time, I created it on my OWN calendar, adding the OOO mailbox as an invitee. All hunky-dory, except for one thing. When I looked at the OOO calendar via Outlook, the new item wasn’t showing up (even though I could see it in OWA). And my manager’s item still wasn’t there. I restarted Outlook. No joy.

Then, at Doug’s suggestion, I removed the OOO calendar from my Outlook view and re-added it. Now both items were showing up, and everything was as it should be. And I still have no clue why things were screwed up to begin with.

Moral of the story: If you get confused by weird behavior with an Exchange calendar, don’t feel bad about it. Even an Exchange admin with over a decade of Exchange experience can get befuddled by such things.