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Q: Recently, and for no apparent reason at all, my Microsoft Outlook has been crashing every time I load the application. I have been running Microsoft 365 Subscription, version 16.59. After clicking on the Outlook icon it appears the application is loading and the initial screen pops up with the log-on box to enter my password. However, this screen only appears for about one second then disappears. A few seconds later a problem report for Microsoft Outlook appears on my computer screen. All other Microsoft 365 programs load and operate correctly, only Outlook has the problem. have attached the screenshot. I hope you will have a solution to my issue. Thanks, I look forward to reading your column every Saturday in the Northwest Florida Daily News.

 – Kelly S.
Fort Walton Beach, Florida

A: Thanks, Kelly!  And I look forward to bringing you each weekly edition, although I fear my readership here in my local area has diminished since the Daily News switched to e-edition only on Saturdays.  I keep hoping the column will be moved back to Sunday, with the other local contributors.  Thanks for being a fan, and a reader of the paper.

Its wasn’t immediately obvious from your question that you are actually running these applications on a Mac computer.  In fact, I wasn’t even thinking along those lines until I viewed the screenshot that you so thoughtfully shared (readers, these usually help a lot for me to understand your issue).  Once I saw the error, I knew that wasn’t from a PC.  Then, when I looked back at your submission, I saw the description of your computer and operating system, which I had completely missed on my initial read through.

It might surprise many readers to hear that Microsoft Office can run on a Mac.  Well, in recent years, the lines have somewhat blurred in the old Mac vs. PC debate.  Not only can Macs run Office, but with the right support software they can actually run Windows itself, and most non hardware-specific Windows applications.  This is the kind of thing that makes bringing you a tech Q&A column more challenging every week.  Thank heavens for Google!

On to your problem.  First of all, I don’t know the way that Office for Macs is structured, but your screen capture appears to say that it’s Outlook 2002.  That seems wildly out of date, despite it reporting a version number of 16.59.  So, let’s start with the standard rhetoric about making sure you’re running the latest and greatest of everything.  Even if 16.59 is a correct version of the latest Outlook, it’s a couple of minor releases behind what is considered current.  Without looking it up, I can’t definitively say whether an issue such as yours was directly addressed in the intervening versions, but it’s always a good idea – especially when you’re experiencing anomalous behavior – to update to the latest version available.

I have no direct experience with the Mac version of Office, but I did some research into your problem nonetheless.  I found that this issue, or one remarkably similar to it, seems to occur when people update their MacOS to Monterey, which I note in the information accompanying your question is what you are running.  With that in mind, I’m going to make the leap of logic that the combination of Monterey and your Outlook version are at the heart of your issue.  If updating your Outlook doesn’t solve the problem, we’ll be doing more grasping at straws.

In the research I did, I found one user who claimed victory over the problem by doing a force quit of Outlook as it was starting up.  In subsequent launch attempts he claims that it launched without any issue.  I can’t imagine why this would fix anything, but I suppose it’s worth a try.  At least, it can’t hurt anything.  Still others have claimed that even though they had the latest version of Outlook installed, a software re-installation fixed the issue.  To me, this makes far more sense than the force quit idea.

So, it sounds like there is something in MacOS Monterey that doesn’t fully get along with certain versions of Microsoft Outlook 365.  It further seems like Microsoft may be dragging its feet in mechanizing a fix for it.  Well, either that, or users aren’t keeping up with the latest software releases! And that, my dear geek Kelly, is where I recommend you focus your efforts.