Mail.app can't send emails

Mail.app (either 3.6 under 10.5.8 or 4.5 under 10.6.7) has lost the ability to send emails. Both can receive/download emails from Yahoo Mail but neither can send messages.
Sticking to 10.6: I've installed Thunderbird which does work "both ways" but I really want my Mail.app back.
This has been a perennial problem going back some versions of OS X and Mail.app. Mail.app works fine for months but then there will be times when the sent emails seem to stall but can be made to send if I first quit the sending process with Activity Monitor, quit Mail.app and relaunch. This will go on for a few days, then NO emails can be sent.
Thanks in advance for any help.

Thanks for your response, William.
First I'll answer your question and then update what's happened over the past 10 hours or so.
Connection Doctor (this is typical) will show two activities - as represented by the "spinning gear" wheels.
Both say: "Connecting to server."
Often: one of the two activities eventually shows a green button and shows a message: "Mail has connected to the internet."
But Mail.app is then unable to connect with the smpt server.
Nothing more happens for many minutes - usually this ends with a message telling me to check my email and network connections.   (I've done those checks dozens of times - nothing is ever changed or incorrect.)
Tonight (after getting notice of your post to my question), I again tried sending a test message (to myself and to myself again - in my hotmail account)
I was preparing to respond to your question about Connection Doctor so I hit "Send" for the test massage and launched Connection Doctor. Again - nothing happened for about 10-15 minutes but Connection Doctor then flashed a message for me to enter my account login password. I entered my password - but "nothing continued to happen."
Finally - without warning - the test message was sent (and the much loved "swoosh" sound was heard)!
49 days: that's how long it's been since I could use Mail.app to send messages. For no reason I can see - the smpt.ameritech.yahoo server RESPONDED!
Yes - I immediately composed another test message and this one went "swoosh" as soon as I hit the Send button.
Next: Tuesday (first business day after Memorial Day) I'll call my ISP and try to sort this out with them. This is NOT a Mac problem. I have proven this: tried to send from both 10.5.8 (Mail.app 3.6), from 10.6.7 (Mail.app 4.5) on my Mac Pro and from my MacBook (also running 10.6.7 and Mail.app 4.5). NONE of these platforms can connect with smtp.ameritech.yahoo server.
You: get a "helpful" rating because, if not for your question about Connection Doctor, I would never have tried (yet again) sending another test message.   I was simply convinced that doing that was useless after many tries.

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