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Mac to Windows Outlook Email Attachments: Save to Disc

by Steve 1 2 3 / September 12, 2012 12:59 AM PDT

iMac 2011: OS 10.8.1 (Mountain Lion); Windows: Various.

This problem is in discussion forums going back to 2008 and before but with no solution yet. A significant proportion of Mac users (and their Windows-Outlook friends) are affected. I am one of those Mac users.

The problem is when a Mac user sends an image by email attachment to a Windows user using Outlook. The Mac user, using Mail, attaches the image (a .jpg) to the message by pressing the paper clip button and selecting the file in the resulting file list. (There are two other ways but they make no difference.) As it appears on the Mac's message window it is open and at the bottom of the message (unless a setting on the Mac puts it in the text). When received by my Outlook users, the attachment is also open and can by viewed, but sometimes there is no icon with the name of the attachment file - only the opened image is seen.

In many cases, the Windows recipient cannot save the image file to disc for later use. That is the problem. In many cases the following do not work:


1. Using Right Click on the opened image (although a Windows friend using Windows Live Mail can use this method);

2. Choosing File > Save Attachment;

3. Clicking on the email attachment icon (often there is no icon);


4. In Mail, Edit > Attachments > Always Send Windows-Friendly Attachments; and Edit > Attachments > Always Insert Attachments at end of message, are both set to on;

5. In Mail > Preferences > Composing > Message Format is set to Plain Text.

Sometimes none of these work.

As far as I know, there is nothing else a Mac owner can do to specify how the image will be sent.

These (at the Mac and Windows ends) are variously given on discussion boards as the solution. They don't work for me and my Windows-Outlook friends.

Has ANYONE got an answer to this long-standing problem please, that works with all Windows users?

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All Answers

Best Answer chosen by Steve 1 2 3

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by Steve 1 2 3 / December 5, 2012 6:51 AM PST
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Amendment to my post
by Steve 1 2 3 / September 12, 2012 1:03 AM PDT

Delete the sentence "Sometimes none of these work. " in my post.

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Mail Version 6
by mrmacfixit Forum moderator / September 12, 2012 9:07 AM PDT
In reply to: Amendment to my post

I know this does not help you but I send picture attachments to my work address frequently and do not have this problem.

We have an Exchange Server and are running Outlook 2010, although I have been doing this since the Outlook 2000

I'm wondering if this is not an Outlook problem.


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Just one.
by R. Proffitt Forum moderator / September 12, 2012 1:08 AM PDT

1. Windows Live.

Sorry but that app has issues. I just nod and tell them to use something else. Some want it fixed but if MSFT can't fix it, why do you expect others to fix it?

It appears that Windows Live continues to apply to the other questions and if someone can't learn that it has issues, give them more time.

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Re: mac mail
by Kees_B Forum moderator / September 12, 2012 1:09 AM PDT

Did you already try to use Thunderbird (free email program) in stead of Mac Mail? is the link.

I don't dare to suggest the Mac version of Outlook. That would be an expensive solution. But Thunderbird is free, so worth a try.


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Let Windows neanderthals deal with it.
by wheresjbob / December 13, 2012 1:39 AM PST
In reply to: Re: mac mail

As a mac user, I'm not installing a different email program because the OS of Mass Corruption (Windows) can't handle something as simple as an embedded image in their email. Why do Mac users have to stoop to the lowest common denominator to accommodate handicapped OS's???

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Its not a separate program
by Steve 1 2 3 / December 13, 2012 3:46 AM PST

I agree, but I didn't make my message clear, apologies: Attachment Tamer is an add-on to Mail. Having chosen a few settings in Attachment Tamer's prefs, (which become part of Mail's prefs.), Mail behaves exactly the same (except for outgoing messages showing in Mail in icon form, which is the point of Attachment Tamer).

Attachment Tamer works perfectly.

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