Emailing photos to Windows users

kallisti

macrumors 68000
Original poster
Apr 22, 2003
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I've noticed problems when emailing photos to Windows users using Mail.

(1) If sending one photo it (sometimes) gets included as an attachment and can be viewed/saved by Windows users.

(2) If sending more than one photo with Mail the images don't appear as attachments for Windows users and can't be saved. Worse, sometimes they can't even be viewed.

For Mac users this isn't an issue, as everything I've sent using Mail can be both viewed and saved.

Usually my Mac "just works." I like how easy it is to drag a photo into Mail, choose which size I want to send (actual, large, medium, small), and hit the send button. When receiving emails (or viewing any content) it's equally easy to just drag attachments/images onto the desktop if I want to save them.

But I'm realizing that Mail doesn't seem to play well with Windows Outlook for sending photos. It's actually kind of pissing me off.

Not sure if there is something I can change in prefs to make this work. Or do I need to install Outlook on my Mac? Or just send images as PDFs which get treated as files/attachments and can be opened on Windows computers?

This is an issue when sending images from my Mac to my work computer to be included in a talk (ended up making a slide of the image in PowerPoint on my Mac and emailing the PP file to my work computer). It's an issue when sending out photos to family/friends who don't all have Macs.

I like Mail for most things, but this is becoming a deal-breaker for me.

Thoughts/ideas?
 
Nov 28, 2010
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I do not have experience with the issue you have, but what about using Mac OS X' built-in compression to (Finder > select files or folder(s) > right click > Compress) to send a ZIP file to Windows users, when you want to send several photos. Windows has a built-in decompression tool, thus ZIP files can be easily opened by Windows users.
 
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Elbert C

macrumors 6502a
Mar 23, 2008
507
98
AK, USA
Have you tried sending Windows-Friendly Attachments? Mail Edit menu > Attachments > Always send Windows-Friendly Attachments.
 

mofunk

macrumors 68020
Aug 26, 2009
2,417
160
Americas
I notice those that use verizon/comcast mail, some of the emails don't go through. If you have a lot of clients/friends that use those type of emails, you can try opening up a gmail account and send it.

Or try CC yourself in the email. After you've done what Elbert C said.


Again, I don't think it's Mail but those type of accounts. I've send just a regular email and it didn't go through. This is way before iCloud.
 

MisterMe

macrumors G4
Jul 17, 2002
10,681
50
USA
I notice those that use verizon/comcast mail, some of the emails don't go through. ...
You are probably barking up the wrong tree. First, a photograph is just a bitstream on the Internet. Second, Verizon and Comcast are pipes for these bitstreams. In order for these two ISPs or any others to block photographs, they would have to monitor all bitstreams and to preferentially block them. To what end?

In all probability, the OP's problem is a user error. The solution to the OP's problem has probably already been posted by Elbert C in Post No. 4.
 

kallisti

macrumors 68000
Original poster
Apr 22, 2003
1,619
5,590
Have you tried sending Windows-Friendly Attachments? Mail Edit menu > Attachments > Always send Windows-Friendly Attachments.
Yes, that is (and has been) checked.

Attachments work fine for other file types. For some reason JPGs are the only ones that don't get treated as attachments.

The compression idea is interesting and one I hadn't thought of. May have to try that. Debating if I want to get Outlook for the Mac.
 

Padaung

macrumors 6502
Jan 22, 2007
462
78
UK
Yup, had the exact same problem myself in the past. If I don't know if the person uses a Mac then I simply send them a zip file just to be on the safe side. Since doing that, never had a person say 'where's the attachment/image?'

Right click on the file/folder: Select 'Compress ...'
 

kallisti

macrumors 68000
Original poster
Apr 22, 2003
1,619
5,590
Update:

I noticed something else happening.

If sending a photo as "actual size," Mail keeps the .jpg extension on the file. If having Mail resize an image (to large/medium/small), it changes the extension on the file to .jpeg. This happens even if "Always send Windows-friendly attachments" is checked. Not sure if this can cause problems for some Windows users.


[Edit]
just saw this response, will see if it helps

Try the app: attachment tamer. It's a Mac mail plugin that will solve your problem.
 
Last edited:

mofunk

macrumors 68020
Aug 26, 2009
2,417
160
Americas
You are probably barking up the wrong tree. First, a photograph is just a bitstream on the Internet. Second, Verizon and Comcast are pipes for these bitstreams. In order for these two ISPs or any others to block photographs, they would have to monitor all bitstreams and to preferentially block them. To what end?

In all probability, the OP's problem is a user error. The solution to the OP's problem has probably already been posted by Elbert C in Post No. 4.

I've been using Apple Mail for a long time. I notice when I send stuff to clients/family and they don't get it, it's because they are using Verizon or Comcast mail. This has happen a lot. I'm speaking from my experience. For example, I emailed a client an email that had atleast 2 paragraphs in the body and attached 2 PDFs. I called the client to see if they received them, and they did not. CC a copy to myself has helped. Also when the client adds my email to their address book helps. If all else fails I send from another account.

This is why I miss the online Gallery page. You could just post your photos from your computer and email the link to your friends so that they can download them or view on the web. No waiting to send/receive huge emails.
 

The Whip

macrumors newbie
Oct 9, 2015
1
0
I do not have experience with the issue you have, but what about using Mac OS X' built-in compression to (Finder > select files or folder(s) > right click > Compress) to send a ZIP file to Windows users, when you want to send several photos. Windows has a built-in decompression tool, thus ZIP files can be easily opened by Windows users.
I know that you posted this a number of years ago and I am new to Mac (1 year) I had the problem sending photos to a Windows user. Tried your fix and it worked great. Thanks much.
 
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