Work-around for Outlook attachment problems
A while ago, a Hawk Wings reader emailed me, asking for advice (often risky; not generally recommended).
He was having a problem with attachments:
When I use Apple Mail to upload an attachment, the recipients are unable to receive it. Particularly, their mail application will display an attachment icon, but there will be no attachment in their mailbox. This was never a problem with Entourage, and I don’t want to have to return to using that program. I’m just wondering if you have ever encountered this as an issue.
Annoying. Having read or heard somewhere that Outlook users in particular have this problem with attachment in Mail.app generated emails and that it is a function of the odd way in which Mail does HTML (“Rich Text”), I advised him to switch to plain text as the default Composing format (Preferences > Composing > Message Format).
That fixed the problem. Something to bear in mind if the same thing should happen to your recipients.
Similar Posts:
- Attaché: Droplet for quick Mail.app attachment lists
- More on international character display problems
- Problems with international text in Mail 2.0
- Extracting winmail.dat files in Mail.app
- TNEF’s Enough: Dealing with winmail.dat files
Tags: Apple Mail, Apple Mail Tips, attachments, mail.app, outlook, problems

April 22nd, 2006 at 11:28 pm
I do have some problems with Apple Mail attachments too. Every month I extract a large text file from a database, which is actually InDesign Tagged Text, ready to be placed into a layout. It is extracted from the database via a web-interface. On the odd occasion that I have saved it on my Mac desktop (from Safari or Firefox) and then attached it to an Apple Mail mail and sent it to myself at work, the files haven’t placed correctly. For some reason InDesign steadfastly refuses to see them as InDesign Tagged Text and places the entire code of the file as a plain text frame.
I haven’t figured out if it’s a Mac character encoding issue of some sort, or whether Apple Mail manages to mangle it somehow along the way.
April 22nd, 2006 at 11:46 pm
Interesting. I wonder why.
No doubt you are using Plain Text as the default format already.
April 23rd, 2006 at 3:07 am
The inverse problem happens too: if Outlook senders are using Outlook’s “Rich Text” format instead of HTML, the attachments will often arrive inside “winmail.dat” files, which are difficult to open. (There’s a program called TNEF’s Enough which can extract the contents of those files, though.)
If the files do import into InDesign from the original machine, I’d suggest zipping the files before you e-mail them. This usually fixes problems with plain-text formats getting mangled.
The InDesign Tagged Text format is a bit tricky with regard to text encoding. In particular, the encoding tag at the top has some special requirements, and your line endings must match the platform that your encoding tag specifies. This knowledge base article is your friend.
April 25th, 2006 at 12:00 am
Check out “Send Windows Friendly Attachment” options when adding a file with the attachment button (not available via drag and drop)
jon
April 25th, 2006 at 12:12 am
Jon, you would think so. But in fact, it doesn’t seem to help much for many people:
http://discussions.apple.com/thread.jspa?messageID=2138572
April 25th, 2006 at 12:20 am
Damn :(