Sending Windows Freindly Email

Q. When I send Windows users a JPEG file from Apple Mail they say they cannot open the attachment. I can send the same file to a Mac user without an issue. What is going on?

A. The problem is that you are becoming a victim of “Windows Friendly” mail messages. When you drag and drop an image into a mail message in Apple’s Mail application it does not check the “Send Windows Friendly” email. The attachment gets broken up after it traverses the Internet.

The file does arrive at the PC but the Windows mail application (or Browser based internet reader) doesn’t see the file correctly. The PC sees a file with the correct name but the wrong MIME type (application/appfile) as the jpeg but also included is a piece with the correct MIME type (image/jpeg). When the Windows user tries to open the file their PC opens the first part, which is not a JPEG and “has no preview”.

So when your sending to a PC user, you should click the attach icon and browse to the file. Select the file and choose “Send Windows Friendly” attachment. The Mac will then send the attachment in “Base 64” and the receiving PC will not get confused about which piece to open.

Windows users can also open the incorrectly sent image by Right-Clicking the attachment and choosing Save As. They can then navigate to where they saved the file and open it. It’s kind of annoying since they’ve probably become used to opening the attachment in the email.

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