Why doesn't Outlook reply to recipient when doing a reply to a sent email? Yahoo mail does...

It does, of course. State precesiley what you are doing and what happens (include any error messages), your mail account type, and how it is configured.

Okay.  In Outlook, I enter my Sent items folder, select an email entry, right-click it and select Reply from the pop-up (or use Alt-R), and voila!  I'm replying to myself.  To attempt to send to the recipient I have to do a Reply All and remove me from the To section.  Annoying.

Are you saying that there is an option that controls this behavior?  If so, I'd love to know where to change it.

Using Microsoft Exchange in a corporate setting.  My local instance is Outlook 2007 SP2 on Windows XP Pro 2002 SP3.

--Rob

There is no need for an option to change anything. Not sure what you were expectring would happen when you reply to the sender in the Sent Items Folder. Think for a minute. Who is the sender of items in the Sent Items Folder? You. Outlook is just doing what you've told it to.

Normally one replies to messages that are a folder that contains received messages. It makes no sense to reply to messages in the Sent Items folder.

Yes, Outlook is doing just what I told it to do.  But that's like jumping off a cliff just because someone told you to.  Doesn't mean it's the right decision.  Microsoft software is always making assumptions about what I meant to do.  This is one time it isn't.

Sure, doing a Reply to a Sent item makes sense.  I sent 40 emails today, and 3 or 4 of them from my Sent items.  I do it all the time to keep the email thread consistent and continue where I left off when the recipient doesn't reply before I have more to say.  Email is my primary communication vehicle here at work.  And, as I said initially, Yahoo Mail already does exactly what I'm asking for, so I know it's doable and it is the right decision.  (And probably rather simple to program.)

So.  Thanks for the reply.  Do you know of a way I can send this enhancement suggestion to Microsoft?

--Rob

Not really. Since it isn't a logical way to use the Reply feature, I doubt Outlook would ever adopt it or consider it an "enahancement." I sure wouldn't.  

I can see that you don't get it.  That's okay.  Thanks for the chat.  I guess I'll look elsewhere.

--Rob

I get what you are trying to do, but why would you? I just don't see any point in it.

If you want to RESEND the email with an edit, then that function is already available to you.

Of course I get it. You would simply not use the Reply Action in the Sent Items folder since that is clearly not the action you want. If you want to send one of those messages to other recipients you would use Forward or you would open and resend the message.

So.  Open the email, go to Options > Resend, then type some more.  Hmmm.  Not exactly what I was looking for, but I could play around with it. 

I heard through the grapevine that Office 2010 removes the sender from a Reply All from a Sent email, so I guess I have that to look forward to, whenever we upgrade here.

If Outlook *allows* you to reply to a Sent email, then Microsoft must have thought people would do it, or they would have prevented it.  My point is that if you're going to allow someone to do it, why not make it useful?  Why allow someone to reply to a Sent email and then code it to send it to yourself?  Yahoo realized that if someone was going to reply to a Sent email that sending it to yourself was silly, so why not code it to send it to the original recipient?  I happen to think it's a great feature, as I *am* in the habit of replying to my Sent emails as a way to keep the email thread intact and continue the "conversation" where I left off.  I'm just forced to do a bunch of modifications to get it pointed in the right direction when I attempt to do this, and would like Outlook to do that busywork for me. 

I've been doing this for years, and it was fairly recently that I discovered that Yahoo handled this situation the way I would handle it, and I was like "YES!  Someone finally gets it!"  So I thought I'd try finding out if Outlook could do it too.  Looks like it doesn't.  So I'd like to suggest it to them.

--Rob

He's expecting the "reply" feature to act intelligently and intuitively, in the exact manner that almost every other mail client does. If there's going to be the option to "reply" to a message one just sent, it's obvious that the person wants to add another outgoing message to the conversation thread. To have this option, and have it just reply to himself is neither intelligent, intuitive, or anticipatory of the end user's needs.

Mail in OSX, GMail, Yahoo! Mail, etc. etc. all do the same INTELLIGENT, INTUITIVE thing (not to mention, the only thing that makes sense as a practical action) when someone selects "reply" from a sent message. It prepares a message continuing the thread to the person you've been sending to. 

You apparently think the job of software is to present fun vocab quizzes ("what is the technical definition of 'reply', moron?), instead of providing an intuitive user experience.