Outlook Express converts my work mail into an attachment, and throws away my attachments.

September 19, 2004 5:11 PM

We use Outlook Express as our main email "manager." Any message I send from my work email to home is received as an attachment. Any attachment that I may have included in my email is now gone. WTF?

The attachment security thing is turned off, and I've sent the email in both rich text and plain text with the same results.

MS Support sucks, and I've tried searching with no good results (seen a few others with this situation, but with no responses in the forums).

It is rare that I need to send something to my home email, but it is really annoying when I do. Please help me, Ask MeFi, you're my only hope!

Disclaimer: Outlook Express is on my husband's machine; he has no problems with it otherwise and is unlikely to change. Yes, he uses IE too. [sigh]

posted by evening to computers & internet (11 answers total)

This best way to troubleshoot this is to isolate all the variables.

First, does this happen to other addresses (ie same thing with work -> hotmail?). If that works we can rule out the outgoing work server as the one causing the problems.

Does your home have web-based mail support? If so try that and if it still shows up as attatchment then it is definitely the incoming POP3/IMAP/Exchange server on your home end and you need to contact the ISP.

If you don't have web-based mail you can check, try using Mozilla's Thunderbird to rule out Outlook being the problem. If you can setup Outlook Express you can setup Thunderbird. Uninstall it after the test if you want.

If that shows everything as coming through as fine then do a repair on the Outlook Express (Add/Remove,... repair).
posted by geoff. at 6:08 PM on September 19, 2004

Are you forwarding the message, or are you creating a new message? Lot's of e-mail clients have the ability to forward messages in-line or as attachements, and if that's what's happening, you probably just need to change the behaviour in the options.

Have you tried dragging the e-mail attachment out of the message and into the inbox? In my client, that creates an instance of the forwarded attachment, and any attachments that were in that message are available.
posted by willnot at 6:11 PM on September 19, 2004

Your work email server/ISP may be filtering out .eml files (email as an attachment).
posted by skallas at 6:18 PM on September 19, 2004

I've seen this when sending emails from "outlook" to "outlook express." You need to change your send-email format (in outlook) from RTF format to HTML format. This should be in the options somewhere, but not having outlook, I don't know where.
posted by seanyboy at 12:25 AM on September 20, 2004

Because I can't bear to leave an answer half answered, here's a bit more information.
posted by seanyboy at 2:21 AM on September 20, 2004

Using geoff's suggestion, I sent a variety of test messages. Everything works fine in yahoo's mail, Thunderbird and the web-based email. So it is def. Outlook Express.

willnot - the problem is in receiving, not sending, and my outlook setup is fine. we tried dragging the attached email into the inbox, but it still didn't have the attachment. lovely, eh?

seanboy - that is exactly the problem (bottom portion). Unfortunately, I tried sending the email as HTML and that still didn't work.

I now have the evidence to convince my husband once and for all that Outlook Express sucks and that he needs to switch to something else. He reluctantly agrees.

Thank you everyone.
posted by evening at 5:05 AM on September 20, 2004

I believe that the problem is more to do with "outlook" sending files in a strange format than "outlook express". I think that thunderbird, et al have worked around the problem, but for Microsoft, they're not as interested in you using "outlook express" as they are interested in forcing you to move to a new client (i.e. outlook).

If emails sent as HTML still refuse to show attachments, then it isn't the problem I said. However, you need to ensure that an email sent from "outlook" to "outlook express" is a new email, not just something forwarded after changing the settings.

I reccomend using Thunderbird. It has some rough edges, and may not be right for the very-non-technical users but I think (personally) that it's a good client.
posted by seanyboy at 5:15 AM on September 20, 2004

This is for Outlook 2002, it might be different for whatever version you're using, and it might not even fix anything since you say the problem is with Express and not Outlook. Still, worth a shot, so go to:

Tools > Options > Preferences Tab > E-mail Options... Button > When fowarding a message (make sure it isn't set to "Attach original message").
posted by willnot at 10:06 AM on September 20, 2004

The problem is that your Outlook is probably set up to format your messages with Microsoft Outlook Rich Text. All of the formatting - fonts, colors, etc. - gets sent as an attachement that Outlook can read, but other email programs cannot. Thus everything, including the content and any other attachments, gets shoved into one un-readable attachment. We had this problem with a client getting odd attachments from our office.

You need to go to Tools > Options > Mail Format and change either to HTML or Plain Text.
posted by rhapsodie at 12:25 PM on September 20, 2004

it is only with Outlook Express that this problem is happening with, and I tried sending Plain Text as well as an HTML message and they both came as attachments. One weird thing is I forwarded an HTML message and it arrived fine.

Doesn't matter anymore as I've converted him to Thunderbird.

Thanks everyone for the help.
posted by evening at 5:37 PM on September 21, 2004

ok, coverting to the latest Thunderbird didn't help. The previous version seemed to receive the files ok, but the newest doesn't (??).

I sent the messages as HTML and seperately as plain text, and neither worked. We're working with another person on this project, who sent me the file directly. I then forwarded that to home and it got there! So I then tried forwarding one of my own messages but that didn't work. But when we sent an email from Thunderbird to Outlook, I replied and attached the files, that worked.

Why does that work? WTF is wrong with my Outlook??? This is driving me insane and I've given up. cries
posted by evening at 6:47 PM on September 22, 2004