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Outlook sends gif, Outlook Express will not send gif

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I'm a news junkie and travel for a living. When on the road I occasionally have a problem that I never have from home. I do my general email from Outlook, but because it is so easy to remove scripts from the code sometimes in news articles' html I use Outlook Express to edit and send news stories to friends and family.

The problem: If I send a news story with the news source's masthead embedded as a gif, I sometimes get an error like this:

"An unknown error has occurred. Subject '"Family renews search for hunter's remains" & "Remains of Texas hunter found in western Colorado"', Account: 'Phillip xxxxxx', Server: 'mail.wildblue.net', Protocol: SMTP, Server Response: '554 mail server permanently rejected message (#5.3.0)', Port: 25, Secure(SSL): No, Server Error: 554, Error Number: 0x800CCC6F"

However, if I just send the article without the embedded gif, it goes through without a problem. But wait, that's not all. LOL

If I take the very same article and copy it from the Outlook Express note that I have prepared, and then paste it into an Outlook note and I re-embed the gif (When I paste it in there's nothing but a placeholder in the Outlook message for some reason.); when I then hit send the Outlook copy WILL send with the embedded gif.

Configurations: I can see NO difference in the configuration of Outlook (Outlook 2003 (11.8118.8132) SP2) and Outlook Express (OE 6 (6.00.2900.2180 (xpsp_sp2_rtm.040803-2158)). Both clients are configured the same, with "My server requires authentication" checked and the information correctly reflected.

Applicable?: The Microsoft Article 290808 (http://support.micro....com/?id=290808) looks similar, but while it starts off looking promising it gets off into Exchange and this doesn't appear to be an Exchange issue...

Summary: Outlook WILL send with an embedded gif, OE will not.

Any thoughts?


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