Why won’t Outlook 2007 show send/receive progress window when I send email?

when I hit send receive, outlook 2007 shows me a progress window with all of the tasks, but when I just his “send” from within an email, I don’t get the progress window. This means if a send fails, I don’t get to know about it unless I notice the tiny warning in the bottom right corner.

Pinning the window doesn’t help, because that just keeps it open, but in the background. I want it to pop up like it does when I hit send/receive. I have also already unchecked “Don’t show this dialogue box during send/receive”

Any settings I can use?

Outlook 2007 running on Windows 7