Email client usability: Replying to your own sent items

Here’s a scenario that I think is fairly common: I’m having an email conversation with another person (“Melissa” in this example). I reply to Melissa’s email; then, later, before I’ve gotten a new reply back from Melissa, I come across additional information that I want to send to her as part of the same email conversation.

To do this, I could just re-reply the most recent message that I got from Melissa – the one I already replied to earlier -- but in that case, my earlier reply would be dropped from the conversation when Melissa responds and the conversation continues:

What I really want to do instead is to reply to my own latest message in the conversation, so that the entire thread of the conversation will be preserved in the message:

Unfortunately, some modern email clients do not have very good support for this scenario, including (as I write this) the latest versions of Microsoft Outlook and Novell GroupWise.

• In Outlook (versions 2003 and 2007), if you Reply to a message in your Sent Mail folder, Outlook populates the "To" field with your own address, instead of populating it with the address (or addresses) of the other conversation participants. If you "Reply to All", both your address and the other participants' addresses are populated in the "To" field. In both cases, you need to fix the "To" field manually to make it have only the recipient(s), and not yourself.
• In GroupWise (version 7), the application doesn't permit to you do a Reply on items in the Sent Items folder at all! (The menu item Actions | Reply is disabled when an email message is selected in Sent Items.) Instead, you are obliged to use the Forward feature instead, and then clean up the header fields of the new message by deleting the "Fwd:" that automatically gets prepended to the subject line, and manually re-entering the address (or addresses) of the other conversation participants.

Gmail does handle doing a reply to a sent item correctly – good job by the usability guys at Google! Some other, older, mail clients may have handled this correctly as well; thinking back to my time at Michigan, I'm fairly sure that the now-venerable Pine email client handled this case properly.

It would be nice if Outlook and other mail clients that behave similarly would put the other conversation participants' addresses in the "To" field (and the "cc:" field when applicable) instead of your own address when you reply to an email message in your own sent items folder.