Problems when sending mail from Outlook to a Mac

[SOLE2000]

I have MS Win XP with SP2 installed on my computer and I use Microsoft Outlook 2003 as my email client. I have a vendor I work with that uses a macintosh running OS X and using Microsoft Entourage as her email client. When I send attachments, they usually end up as winmail.dat files on her end, be excel, word, or just about any other type of document. The odd thing is that this only happens to me when I send to her, and she only has problems from the mails I send. I've resorted to attaching mails in yousendit.com, but this is quite annoying sometimes.

Any ideas as to what settings could be affected, or what we could fiddle around with to fix this problem?

[nialler]

Hi Sole

Let me try and recreate the problem now, I have the pc with outlook 2003 and the mac right beside it with Entourage on it (SP2) to be honest I haven't seen this problem in years.


if all else fails this is the solution:

http://mac.softpedia.com/progDownload/TNEFs-Enough-Download-5130.html

Nialler

[SOLE2000]

Thanks NIALLER!! If it helps, I found out that when I send ZIP files there's not problem, so that's the way I'm working around this problem for the time being.

[nialler]

ok just kinda recreated it, the only way I could do it was to send a plain text email. Under your tools menu under option select mail format, in the internet format button do yo have the Encode attachments in UUENCODE format ticked? As I ticked it and I got the .dat files

That could be a remote possibility.


zip files will work perfectly but it's still a pain having to do that.

[SOLE2000]

Nialler, it's unticked, but you seem to be getting somewhere... The problem's not only with plain text messages, but also win Word and excel files (the 2 I mainly send her). These are created using Office 2003 pro. I'm going to read up on this and see if I can find anything on it myself.

Thanks m8!!

[nialler]

No problems, personally when I sent from Outlook 2003 2 excel files in HTML format (rich text) they came over fine, it was when I sent as plain text that the problems started appearing, and actually the only way I can recreate the winmail.dat file is with no file extensions on the attachments I'm sending ie (.xls .doc).

I'm surprised at this happening as I haven't seen this since outlook express 4 on the mac, that was late 90s (though I still know some dinosaurs using it).

[jdc2000]

The problem looks like it might be a security setting on the receiving computer. If .zip files work, try a .txt or a .jpg file. If those work, but .exe, .doc, .htm, or .xls files do not, then it could be that the receiving (or maybe even the sending) e-mail program won't send/receive the files in the normal format or with a normal extension because they could contain a virus.

[SOLE2000]

I thought about that, but the main problem is when I send to the other computer. When she receives from anyone else, she never has any problems, and I don't have any problems sending to any other person (including mac users) as well...

I mind boggler, wouldn't you agree??

[jdc2000]

I'd try sending a problem attachment using a different e-mail program. If you have web mail access, you can try that. Or you could use Outlook Express or one of the free e-mail clients to send a test message. You don't need to replace Outlook as your default e-mail program, just use something else to send a test message. That should help to determine if your copy of Outlook is the problem.

[nialler]

I'd try sending a problem attachment using a different e-mail program. If you have web mail access, you can try that. Or you could use Outlook Express or one of the free e-mail clients to send a test message. You don't need to replace Outlook as your default e-mail program, just use something else to send a test message. That should help to determine if your copy of Outlook is the problem.


Outlook is without a doubt the problem, in fact it's the attachment encoding that is the main issue, I would nearly guess at the fact that if you were to send a single attachment the problem wouldn't occur, the times I've seen this happen on another email client than entourage on the mac has been when multiple attachments having been sent (hence sole having to create a zip archive), I barely recreated the problem last night but I had to fiddle with outlook on the pc, if it's a standard install going through your isp then there shouldn't be a problem.

Sole one thing I didn't ask you is are you going through a local proxy/mail server type thingy that isn't exchange and isn't your isp? As that may be the problem.

[SOLE2000]

nialler, I'm thinking it might be outlook too. The problem is with single or multiple attachments... it's just that I resolve this problem with a zip file.

I'll be perfectly honest, I use my company's email server, which I know is hosted outside of the company and is neither our ISP nor a dedicated server for us. I can almost bet that it isn't an exchange server. The odd thing is that other colleagues within the organization can correctly send files to my vendor's mac, although they are using outlook EXPRESS... which is what leads me to believe it's my outlook that's giving the hokey results.

[Tuttle]

There's a setting in Tools | Options | Mail Format which controls the format Outlook uses to send emails. Do not use Microsoft Outlook Rich Text; stick to Plain Text or HTML instead. Microsoft Outlook Rich Text is an Outlook-only format, and anyone else will just see a winmail.dat file they can't do anything useful with.

[nialler]

Yep Tuttle

That's what most of the sites are saying.

Sole have a look at this article.
http://www.pchell.com/support/winmaildat.shtml

[SOLE2000]

Hey guys, thanks for the help... odd thing is that the mails I send are in HTML... just tried sending one to make sure. Will try sending one to my vendor in plain text and see if this helps.