troubleshooting Question

Winmail.dat - what is the best fix (at the sending server level?) so senders don't have to be bothered and receivers know they will get the PDF attachment?

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BeGentleWithMe-INeedHelpFlag for United States of America asked on
ExchangeiPhoneOutlookMicrosoft 365SBS
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When users send emails with attachments like PDFs from SBS 2011 standard server (they are using different versions of outlook on their desktops), it shows up sometimes on  iphones as a winmail.dat file.

I've heard that's a common issue with outlook at one end and iphones at the receiving end.  The receiving person with the iphone can look on their desktop and got the mail with the correct pdf or similar attachment.

But I got a bit confused while troubleshooting.

I had 1 user send me an email with PDF attachment to a gmail account and looked at it on my iphone (with latest ios version) using the native iphone mail app..  It came in as a PDF file.

I had the same user send me the same PDF to a POP mail account and looked at it on that same iphone and it came in under that account as a winmail.dat attachment.

I am thinking why they came in differently, but then thought - have to check how the contact is in the address book - to turn off / on rich text?  

So the issue is at the sending end?  Is there a way to force a fix on the SBS 2011 server? So senders don't have to tweak all their contacts for people with iphones.  and receivers don't have to deal with winmail.dat 3rd party apps (at least from mail this client sends).

And if you don't have rich text, you lose bolding / fancy signatures?
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