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jpeg attachment probles when sending from Mail to windows mail applications

hi guys. I hope someone can help me as I have been going round in circles for months with this problem.
The task is to send a jpeg attachment - simple isn't it!
No problems attaching it, whether is embeded or viewed as an icon, that's ok. i have selected the option "always send windows friendly attachments" too.
The problem is on the other end. Pretty much every time I get an email back saying that the images are embeded on the email and cannot be saved (right click, save as...) nor they appear listed as attachments. Not only that, but most times they also appear deformed with weird dimensions and loss of quality.

Can someone help me out here, as you can all imagine sending images is pretty common these days, and whether we like it or not, most people use PCs still

MacBook Black, Mac OS X (10.5.7)

Posted on Jul 10, 2009 6:09 PM

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10 replies

Jul 10, 2009 7:53 PM in response to daniel Ponce Taylor

Tell them to use a standards compliant email client.

Now, you may think that is a bs solution. But, alas, it is the answer. Outlook and Outlook express are pretty much only Microsoft Standard.

There are also issues with mail servers; either your ISP or their ISP. But mostly it is Outlook.

Try sending plain text messages with the jpegs attached. There is also an attachment option to always place attachments at the end of messages. There is a bug, though, that prevents you from adding attachments unless you have text in the message body.

Jul 10, 2009 11:36 PM in response to daniel Ponce Taylor

as you can all imagine sending images is pretty common these days, and whether we like it or not, most people use PCs still


As you can imagine, if your problem was constant, with every other user, then someone would have fixed it. In order for you to be able to know exactly what to fix you need to do some testing.

Are you using POP or IMAP? With which email provider?
Have you tried sending mail from a temporary User account you set up on your Mac?
Do your jpeg attachments work with other Mac's?
Do your jpeg attachments work with other PC's? Did you try several different friends?
Have you tried compressing your file into a .zip file before attaching it?
Have you tried sending an attachment from a free Gmail account?
Have you tried using a different email client program like Thunderbird?

What we can't tell from your message, is the problem on your computer, the receiving computer, the email client, the user account, file corrupton, the receiver's email server, some security software, etc.

The answers to the above questions should help us pin down the exact cause of your problem.

Jul 11, 2009 8:01 PM in response to dechamp

Hi Dechamp

Here are the answers to your questions. Thanks in advance

Are you using POP or IMAP? With which email provider?
POP - gmail and hotmail
Have you tried sending mail from a temporary User account you set up on your Mac?
Yes, same problem
Do your jpeg attachments work with other Mac's?
They do when I send to Mac users
Do your jpeg attachments work with other PC's? Did you try several different friends?
I have tried with many users. Our company new uses gmail as an email server and most (99%) of our employees use PCs. 9 out 10 emails I send with images I get the same response, so I have to copy the images, transfer them to a PC and send them from there!
Have you tried compressing your file into a .zip file before attaching it?
Nope
Have you tried sending an attachment from a free Gmail account?
Yes, from the server it works well, it's only when using from Mail
Have you tried using a different email client program like Thunderbird?
No

Thanks for your help

Jul 11, 2009 9:25 PM in response to Nancy Fredrickson

I'm afraid that you don't really have the same problem. You may have the same symptoms but you are not using the same email program, the same server (unless you are also using Gmail), and you are encoding your emails in a Mac specific format.
http://kb.iu.edu/data/abzn.html

I did find a tech blurb that said: "On the Macintosh, the default encoding method for attachments has been changed from BinHex to AppleDouble. This default works across platforms with all MIME-compliant email programs, including Eudora and Microsoft's Outlook Express and Outlook 98."

I quit using Eudora when OS 10.2 came out, so I don't know much more about changing your method of encoding. I checked and the last version of Eudora came out in 2006. Qualcomm has discontinued development for Eudora and none of my clients are using it since it has become a dead end. The last version of Eudora is reported to work with Leopard if you make some changes in the sound files. There is still access to the support forums here:
http://eudorabb.qualcomm.com/forumdisplay.php?s=0936570a42fd9c7b0631c91819e3d099 &f=10

I guess that Thunderbird is the recommended program for Eudora users to migrate to if you don't want to use Apple Mail.

You should probably start your own thread with the words "Eudora Attachments" in the title so that people who are using Eudora will see the name of the program and respond with up to date information.

Jul 11, 2009 11:06 PM in response to daniel Ponce Taylor

POP - gmail and hotmail


I don't know of an issue like this with Gmail. I've only got a little experience with the POP Livemail that Microsoft is now using, but I also haven't heard of any general problem with Mac's on it.

Have you tried compressing your file into a .zip file before attaching it?
Nope


This is a common work around for testing attachments. Windows users should be able to open a .zip attachment, and they do not get attached 'inline' in the email you send.

Have you tried using a different email client program like Thunderbird?
No


This might also help figure out where the problem is happening. If the same thing happens with a different email program, then we can rule out Apple Mail as the problem, and look at some sort of network issue or a problem with Leopard itself.
http://www.versiontracker.com/dyn/moreinfo/macosx/10207484

Aug 4, 2009 12:02 PM in response to daniel Ponce Taylor

Hi, I've believe finally figured this out after a couple of years of frustration with this issue. It is a bug, not a user or end user issue as many blogs indicate. I took my mac into apple and they couldn't figure it out. I had my clients IT people try to figure it out, they could not. The windows friendly attachments isn't the main issue. I'm a graphic designer and send many clients jpegs throughout the day, most, not all, were not able to open the jpegs the same day I started using a new intel mac, (over two years ago), I've been working professionally on a mac for 21 years. G4 mac and powerbook were fine never had that problem or with prior macs. Once I complete migrated to the new mac emailing myself jpegs and then sending them on became a pain.
I experimented with .jpg vs .jpeg, etc. didn't matter, it didn't work. Same problem with .tif, tiff, but never pdf. The clients don't want to be bothered with converting my pdfs to jpeg, so I began zipping the files, which worked. I converted my text in mail to plain text (shift, command, T under format menu). I start a new message when sending jpegs, without my signature or reply to clients email with their signature. One client could now read .jpeg or .jpg where window friendly attachment was selected or not. Another could now read them too, but only when I selected it. Neither could before, and neither could their clients when they forwarded my email. Now, it's fixed! I send sooooo many files on a daily basis and almost all are on a pc. Good luck!

Oct 14, 2009 2:56 AM in response to freshcharlie

Hi. I have the same problem in Snow Leopard.
The method proposed here doesn't work. (This has also been a problem for me and here's how I get it to work.
I always go to the very end of my composed message (cursor flashing, ready to insert) AFTER all signatures etc and then add the attachment. Then it sends and is received no problem.)

I, also, make my file PDF or archiving but not all my clients now how to work with computers, doesn't have to install something because I can't send simple pictures for them. I look like I'm an amateur so now I sent all my pictures from my web mail. It is not good for me, but is good for my clients.

I hope apple to solve this issue soon.

jpeg attachment probles when sending from Mail to windows mail applications

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