Outlook Express and S/MIME

Augh, what a fucking pain in the ass. On a mailing list I'm on, people started complaining about my sending out digitally signed messages. Checking their email headers it looks like the ones complaining are using Outlook Express.

Problem number one, when Outlook Express gets a digitally signed message it displays a somewhat confusing message in the message pane when the user goes to read it. You have to click on a button to see the actual message, There is a checkbox to say not to display the message again, but it's still confusing to the user. I had one person say they thought it was spam. Which, if you don't know what a digital signature is, is understandable. How many valid emails ask you to click in a box marked 'Display Message'

Problem number two, if you click reply to a signed message, OE automatically selects the 'sign' option. This isn't bad in theory, but if you don't have a certificate it complains and won't send the message (unless they deselect 'sign'). Once again, to someone who hasn't ever seen or heard of a digital certificate, they just see that they tried to reply to me and got an error. And there is no way to change this behavior, at least that I could find. If anyone knows of how to turn it off please let me know so I can pass it on.

Thank you Microsoft for providing me with yet another reason to get annoyed with you.

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This page contains a single entry by Gregory published on November 11, 2003 11:19 AM.

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