Outlook users' problems with Apple mail attachments

Folks on Windows XP using Outlook 2003 are having problems with email from Apple mail. Apple mail is using Windows Friendly Attachments and Rich Text as the settings. Sometimes attachments (Word, Excel, PDF) come in fine with an additional .htm attachment, but the body text of the message is missing. If the Outlook user opens the .htm file, there is the body of the Apple mail. Testing with Plain Text results in the body text appearing fine in Outlook, but the attachment is seen as a *.dat file and of course can't be opened. The Macs are all on OS X Tiger with all OS updates applied. Users of Outlook in other offices don't have this problem, and users of Thunderbird on Windows don't have this problem. Any ideas on what is causing this and how to resolve it? Is there a setting on Outlook that needs to be tweaked? Is there a setting on Apple mail that needs to be tweaked? Apple mail attachments to this Windows office worked fine until a few weeks ago. I do not know what changed between then and now as I am not in charge of the computers at the Windows office. Could a Mac OS update have caused a problem? Something on Windows or Outlook specifically? Thanks for any help you can provide. I've scoured the web and have tried everything to no avail. Zipping attachments, while a workaround, is not a long-term solution. Thanks!

Is this in an environment where an MS Exchange Server is being used? Seeing a file change to .dat would often point to that.
Plain Text should be the plan of action for users of Apple Mail, but something (probably the Exchange Server) is messing that up. See:
http://support.microsoft.com/kb/138053
and also related:
http://www.pchell.com/support/winmaildat.shtml
Moving to Leopard would probably not solve this -- the administrator of the exchange server must act.
Also the problem with winmail.dat files is known to impact other email clients used even on Windows computers.
Ernie
Message was edited by: Ernie Stamper

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Is there a problem with Apple Mail using IMAP? Having a problem syncing to our mail server: doesn't sync properly when multiple devices use same mail acct. Spoken w/ mail hosting provider who says Apple Mail doesn't follow IMAP protocol properly leaving Apple Mail users to experience a variety of problems when connecting to IMAP accounts. Among them:
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Question: Is the hosting provider correct in faulting Apple Mail?
Been fielding the question with a number of people. I'm aware of three people who are experiencing similar problems, each using different mail hosts. Tech reps at inmotionhosting.com and nexcess.com point the finger at a Apple Mail, along with an IT specialist in Los Angeles, CA, and a tech support rep at an Apple Store in Arizona who said that Apple and Google mail are aware of and coordinating to resolve the problem.
Anyone out there have any insights into this?

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In the iCloud pane of System Preferences, uncheck the box marked Mail and check it again.

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I'm keen to integrate my Gmail Account with Apple Mail via POP3, however having followed the instructions given by Google - it doesn't seem to work correctly?
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Hi,
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ATT00001.htm attachment in Outlook when sent with Apple Mail

Hi,
This issue was highlighted previously
ATT00001.htm shows up along a Mail attachment
http://discussions.apple.com/thread.jspa?messageID=8433141
Apple mail compatibility issues / ATT00001.c
http://discussions.apple.com/thread.jspa?messageID=8239867
Both of these topics are locked so I couldn't comment about this annoying issue there and had to start a new topic.
Looks like no-one is able to get to the bottom of this very annoying issue including Experts Exchange who I signed up for to see the answer they had given (their website is ranked highly in Google for this problem).
I thought I would post the comments from Experts Exchange here to save anyone signing up for a free trial just to get their answer like I did...
Title:
Mac Mail att htm issue in outlook
Question:
I'm using mac original mail software. I did set my HTML style template. The software is best ever.
And works good when I send email to outlook users on PC. However if I attach PDF for example, it does go through and outlook users get it, however when they open message all they see.
- attached PDF
- and att00001.htm file which has inside email text
Not everybody gets idea to open it and thy think it is empty email. The same email will be sent to apple user everything looks properly. Why email text is converting into the htm file? It happens only if i attach something to my message, if I don't then email text is not being converted to htm attachment.
I think there are a lot of user that know this issue, did anybody find a solution yet?
Thank you
jhyiesla:
I don't think there is anything you can really do about it.
I think that it's how the receivers program is going to interpret it.
For example, I sent an email to my Outlook account from my Mac with just an attachment; no text. I looked at the email in Outlook 2000 and I see the attachment as an item in the body text section of the email. When I look at that same email in Outlook 2003 the attachment shows in the attachment area under the subject line and the body text area is blank.
Then I sent another one with an attachment and some text in the body of the email. In Outlook 2000 I see the text in the text area and the attachment as well as a attxxx file in an area at the bottom of the email. The att file was empty. In Outlook 2003 that same email as the attachment and the empty att file in the attachment area at the top and under the subject line and in the body text area of the email is the text that I typed.
Although Mac Mail uses standard protocols, which is why you can send an email to a Windows PC, it just does some different things. In the WIndows world Outlook and Outlook Express also handle some things differently.
Goldblum:
Thank you for your reply
This issue makes mail.app useless, do you have any recommendations?
Other client which are as good as the mail.app or would be nice to know what is forcing to convert body text to attachment? I could reduce beautiness of my email template by taking out header (jpg) or not using rich text. What exactly is forcing outlook to convert body to attxxxxx.htm file?
jhyiesla:
I truly don't know the answer to that question. Sometimes similar things happen coming the other way. I'll get emails in to my Mac Mail that have jpg files and I'll see the actual pictures in the body of the email.
I happen to also have Office 2008 for the Mac installed and when I sent my self a message and looked at it in Outlook 2000 and XP, the email looked "normal" in all instances. The attachment was marked as an attachment, text was where it should be and no att file.
There are other email clients that would probably work on the Mac like Thunderbird... but I'm guessing that you'd have a similar thing as happens with mac mail. Still it might be worth the download to test it out.
Goldblum:
I used entourage and same HTML template for email and have no problems. It is just so that entourage is as any other MS product "broken" out of the box but did good job and same message is not being converted to HTML attachment when it goes to outlook on PC. I will continue researching internet because it has to be solved. I can't send a message to client without comment to attached invoice. This is so not professional. I will play more with settings of mail.app to see what else can be done to avoid conversion.
jhyiesla:
Entourage probably works well with Outlook because they're both MS products and MS is going to have somewhat similar looks to all their Office products... although there is quite a bit of difference between Entourage and Outlook.
Here's a link that may help you on your search:
http://email.about.com/od/macemailclients/tp/free.htm

As mentioned, Outlook is not email standards compliant. It probably never will be based on Microsoft's history. However, I think there are various issues involved in the problems people have. I often send emails from home to my Outlook account at work. I have never experienced any of the problems that I've seen posted anywhere regarding Mail and Outlook.
My conclusion is that there are issues with certain Exchange Server configurations and/or issues with your own ISP mail server causing the issues.
I do have my system set up to Always send windows friendly attachments (from what I've read, this really is 'send Outlook friendly attachments'), and always put attachments at the end. Prior to the 'always put attachments at the end,' I wasn't having any issues, either. However, I read that that setting helped with other email clients, so I use it.
The obvious question is, "well, how is your exchange server configured." I would love to provide the answer to that question; however, I work for a DoD organization, so actually tracking down the person that knows the answer to that question will take somewhere between five years and never. With my 20+ years experience with the DoD, I'm leaning towards the never end of the spectrum. The other half of the equation is, "I'm using cox as my ISP."

ATT00001.htm attachment in Outlook when sent with Apple Mail - SOLVED!

Hi All,
We recently discovered the problem where emails with attachments sent from Apple Mail were being received in Outlook, blank but with BOTH the attachment and the email itself as an ATT00001.htm attachment!
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I hope this helps...

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I know it's a problem with my local Mac Mail client, since:
I can see the attachments perfectly in my webmail
I can see the attachments perfectly in my other Mac's Mail client, as well as on my iPhone and iPad.
This is a sample of what it looks like:
--Apple-Mail-6-682963542
Content-Disposition: inline;
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Content-Type: image/png;
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Content-Transfer-Encoding: base64
iVBORw0KGgoAAAANSUhEUgAAAyMAAARYCAIAAACd85seAAAWdmlDQ1BJQ0MgUHJvZmlsZQAAeAGt
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nGgJtDraFH0AHYCOQ2eiS9AX0dfQ99BP0a/R3zEYDDNGBKOCIWJcMMGYREw+pgrTiunDjGOWMBtY
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Get info on the drive. What format? FAT drives may be behave erratically for heavy-duty use of the kind you are doing. It's okay to leave a flash drive FAT formatted for light use but for heavy-duty file transfer I think you can encounter issues.
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Message was edited by: homeBased

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Hi There
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