Outlook and Outlook Express Users Want to Reply to Digitally Signed E-mail

You are probably reading this post because you are an Outlook or Outlook Express user and you tried to reply to a digitally signed e-mail from me. The result was a warning/error notice stating, "You cannot send digitally signed messages because you do not have a digital ID for this account." or some such thing. You are receiving this notice because Microsoft made a mistake in the default configuration settings when it packaged Outlook and Outlook Express for distribution.

You have three options for resolving the issue:

  1. Easy/Fast: When composing your reply message go to the "Tools" menu and select "Digitally Sign" so that it will remove the check mark. Then you will be able to send the message without issue. Unfortunately, because of Microsoft's mistake you will have to do this each time you reply to me but it's way faster than copying and pasting stuff.
  2. Moderate/Medium: Stop using Outlook or Outlook Express. From both a personal and professional perspective I recommend against the use of Outlook or Outlook Express and suggest that folks use Thunderbird instead. I have taken this position for a number of reasons, most of which are security related.
  3. Complex/Slow: Get your own digital ID and install it into Outlook or Outlook Express

I use a digital signature for my e-mail in order to mitigate a number of risks associated with e-mail.