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How do I send a JPEG photo (from Mail on my MAC OS X) as a separate attachment w/its title to a Windows PC (and not have it arrive just embedded in the text) ?

I've tried both the plain and rich (html) format to send the JPEG formatted photo as an attachment, but it always arrives in the Window PC as an image embedded in the text section of the email. I need the JPEG photo to arrive with it's original title as a clearly separate attachment. Please help!

iMac, iOS 7.1.1

Posted on Aug 11, 2014 2:43 PM

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12 replies

Aug 11, 2014 3:20 PM in response to Phingari

The best solution is to tell your recipients to use a better email client that is standards compliant, but that likely won't get you anywhere.

The problem you describe has been a long-standing bug in Outlook.


There is an add-on called AttachmentTamer (noted on the link Kurt Lang posted) which will alter the email encoding such that it is acceptable to Outlook's idiosyncrasies.

As a free option, you can try setting the options to Always send Windows friendly and Add attachments to end of message.

Another trick to get Outlook's attention is to immediately change the Font at the beginning of the message, then add the attachments as necessary.

Aug 11, 2014 6:35 PM in response to Kurt Lang

My mistake, I thought the OP said this,

but it always arrives in the Window PC as an image embedded in the text section of the email.

That is purely a function of how the email client decides how to display attachments. No matter how you encode the attachment, the email client should be able to display it however you'd like.

Outlook cannot handle what it refers to as "internet email." It is designed around its own mail server and has never been coded to completely handle email-standard emails.

Aug 12, 2014 5:10 AM in response to Barney-15E

Hello. As Kurt Lang has pointed out, I'm trying to use the Mail program that came with my OS X Mac. If I can't find another solution, I'll probably buy and try the AttachmentTamer that you both seem to know about.


One surprise I've found is that if I DISenable the "send Windows friendly" the JPEG attachment will go through to a PC as an attachment on the attachment bar, but it's a bit bizarre - there appears two attachments for the same photo in two separate sizes (648 KB and 87 bytes for example) - you click on the small one and there's nothing, but on the reg. size one, the photo is attached just as one could wish for. This is not very elegant, I still would like to find a sure solution.


Thank you for your time.

Aug 12, 2014 5:21 AM in response to Phingari

That is the AppleDouble portion of the file that the "Windows-friendly" version omits.


Your e-mail is being sent the same way regardless of the attachment setting. The only difference is a single word in the message - "attachment" vs "inline".


AttachmentTamer is the only solution. This has been an issue in Apple Mail for ten years at least. It is only a single word that needs to be changed so obvious it isn't ever going to get changed.

Aug 12, 2014 6:34 AM in response to Barney-15E

Outlook cannot handle what it refers to as "internet email." It is designed around its own mail server and has never been coded to completely handle email-standard emails.

I have to say I don't understand the reference. By "its own mail server", do you mean a server running Outlook Exchange? If so, that doesn't apply to me, or I would imagine, many users of Outlook for Mac. My mail server is through InMotion Hosting, where my business web site is hosted. Outlook behaves pretty much like any email client I've ever used (though I won't use Mail). Emails I get from hundreds of sources all appear normally, whether they're straight text, or HTML.

Aug 12, 2014 6:36 AM in response to Kurt Lang

Kurt Lang wrote:


Outlook cannot handle what it refers to as "internet email." It is designed around its own mail server and has never been coded to completely handle email-standard emails.

I have to say I don't understand the reference. By "its own mail server", do you mean a server running Outlook Exchange? If so, that doesn't apply to me, or I would imagine, many users of Outlook for Mac.

As you are running a Mac, I wouldn't assume that you would be running a version of Outlook written for a "Windows PC." So, yes, none of that applies to you.

How do I send a JPEG photo (from Mail on my MAC OS X) as a separate attachment w/its title to a Windows PC (and not have it arrive just embedded in the text) ?

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