Apple mail image in signature showing up as attachments in outlook 2010

We have several users in the office that use apple mail with our office 365 subscriptions.  When they user our logo (as any image type, gif, png, jpg) in their email signature it shows up as an attachment with our outlook 2010 clients.  This is annoying but causes a real problem when they forward an email thread.  Because their signature is at the top of the message, it cuts off everything below and it shows up as an attachment in the message.  

This isn't apparent to many of our users in outlook so they don't even check the attachments.  I've googled around and seen many suggestions for settings in mail such as:

Edit > attachments > always send windows-friendly attachments &
edit > attachments > always insert attachments at the end of message

These are both checked and it still doesn't work.  It's definitely the image logo in the signature because when you delete the image, the message forwards fine.  

Does anyone know of any work arounds that don't involve switching mail clients on the mac?
Who is Participating?
I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Vasil Michev (MVP)Commented:
I'm afraid the problem is exactly the client they are using, which is not really supported with Office 365. Perhaps you can get them to put the signature as a transport rule instead? Not really a good solution, as it will append it to the end of the message, but still.
Eoin OSullivanConsultantCommented:
This is a known problem with Apple Mail --> Exchange/Office 365 --> Outlook interactions.

Apple Mail uses plain text and RTF mail formats (but not HTML) whereas Exchange/Office 365 prefer plain text and HTML.

This problem occurs when Apple Mail emails with embedded graphics in signatures are routed through an Exchange server and arrive on Outlook email clients .. the content of the email is slightly confused and Outlook tries to reformat it.  The usual solution is for Outlook to treat the email as an attachment.
If you send the email from Apple Mail to Gmail and then forward it you shouldn't have the same problem which indicates it is related to Outlook processing the email.

I'm afraid the solutions are all work-arounds
1. Change email clients for OSX users to Outlook 2011 ($$$)
2. Move signatures on Apple Mail to the end of the email (not realistic)
3. Make the signatures on Apple Mail HTML based instead of the RTF format that it uses by default .. I've covered this issue in various formats and how to do this in several other posts

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
asgJimkAuthor Commented:
I will try the html route and let you know how we make out.
asgJimkAuthor Commented:
The apple users decided it wasn't worth the trouble of creating an html signature.  Thanks for the solutions.
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today
Office 365

From novice to tech pro — start learning today.