Doug Behl and Ken Getz: Avoiding the Microsoft Outlook Winmail.dat problem |

Doug Behl and Ken Getz: Avoiding the Microsoft Outlook Winmail.dat problem

Q: I use Microsoft Outlook, but a lot of folks I send emails to do not. I get complaints from some of my friends (especially those that read my emails on their iPhones) that rather than message content, all they got was an attachment named winmail.dat. They can’t open the attachment, so they can’t read the email I sent. It’s awfully frustrating for everyone involved. Can you let me know how to fix this problem?

A: This problem has been around for years, and you would think that by the time the umpteenth version of Microsoft Office had shipped (the current version is Office 2016), Microsoft would have fixed this problem. It has plagued both of us on and off for a long time, and we’re glad this question came up, jumpstarting us into finding a solution.

The solution exists, at least in Office 2016, and it’s simple. The problem occurs because Outlook does its best to ensure that whoever receives your email gets the appropriate fonts and layout information. In doing so, Outlook packages up your email in a standard format, called RTF (Rich Text Format). Unfortunately, the rest of the world may or may not understand the RTF file format. When an application attempts to load an email from you and it doesn’t know what to do with it, it simply displays the package containing your email, called winmail.dat.

To fix the problem, Windows users can select File > Options > Mail, scroll down until you find the Message Format option, and make sure Outlook is set to convert RTF messages to HTML format (you’ll find a list of options to choose from). Click OK to save your changes. All modern email applications support HTML-formatted messages, so this change should fix the winmail.dat problem.

iPhone won’t charge

Q: My iPhone was working great. All of sudden, it simply won’t charge. I plug it in, and nothing happens. I’ve tried several cables, and several chargers. I’m not sure what to do, but I can’t go much longer without charging it, that’s for sure. Do you have any suggestions?

A: This actually happened to Ken recently, and then we got this question from a reader; it clearly happens more often than we would have thought! In any case, the first thing to do when weird stuff like this happens is to contact Apple (or your phone’s manufacturer). When Ken called in, even though his phone was no longer under warranty, the phone technician quickly diagnosed the problem and provided a simple solution.

In this particular case, the first thing to do is verify that there’s not some debris in the charging port making it impossible for the charging contacts to connect. It’s hard to see inside the tiny opening, but you can try using a can of compressed air to blow out fuzz or other debris. (Do not, under any circumstances, poke inside the opening with a sharp, metal object—this is almost guaranteed to break fragile connections inside the charging port. If you must, at least use a blunt, plastic object to poke around in there!)

In Ken’s case (and in the reader’s case), fuzz wasn’t the culprit. Talking with the tech support specialist, the solution became clear, even if it seemed unlikely: Reboot the phone. That’s it. Just completely turn it off, let it sit for a few seconds, and then turn it back on.

In every case we’ve heard of, this solved the “it won’t charge” problem. Clearly, there’s something in the phone’s software that convinces it that it no longer needs to charge, even when it does; turning it off and back on clears this logic and resets the charging.

It may be obvious, but heed our warning on this: If you find yourself in a situation in which your device won’t charge, don’t completely drain the battery, or you won’t be able to reset it and start charging again. If charging isn’t working, deal with it immediately. If you find that resetting doesn’t solve the problem, contact the manufacturer for further assistance. It could be a hardware defect, or you might need a new battery.

Doug Behl and Ken Getz spent years answering technical questions in private, and are minimizing the questions by pre-emptively publishing the answers. Submit your own technical questions to

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