Vista: Windows Mail often requires two sends

I'm using Windows Mail with Vista Home Premium. I am having a frequent problem sending mail.

It often (usually) happens that when I try to send mail (it doesn't matter whether I use send or send/receive) the info window comes up but there is no progress. If I wait long enough it will time out.

However, whether I let it time out or just click the "stop" button and then send again, the send operation works 100% of the time.

This has been working like this ever since I got my system in 8/07.

My configuration would seem to be correct because the mail always goes out and is correctly received.

Googling has not produced any information on this. The only thing that I've found that is close, but is not the same, is mail getting stuck and people having to take action to unstick it. This is not that. I just have to try a second time and it works.

I've been living with it, but it's annoying.

Any ideas would be appreciated.

Thanks,
David

 

I guess I wasn't clear. This happens all of the time. The scenario is typically:
>>> collect email <f5> (send/receive)
>>> read some email
>>> write a response
>>> <alt>s to send --- I have my software configured only to send things from my outbox when I direct it to (either hitting <f5> to send/receive or <alt>t s s to send all)
>>> the windows mail info window comes up and says "connected" and just sits there until it tells me that my smtp server has not responded for 60 seconds... or until (knowing this issue exists) I see that it will not progress and just dismiss it.
>>> send again (either <f5> or <alt>t s s) and this time it will work

This happens whether the machine has been idle or active and whether email has been idle or active before. It makes no difference whether there is one message waiting to go out or multiple messages.

Also, after sending some email, might decide to write another email. After writing it and hitting send to put it into the outbox, the same scenario continues. That is, I will try to send the email and it won't go until I try a second time. Then it gets sent just fine.


It kind of feels like there's something that is not getting reset and going through the first attempt resets it but requires a second try to make the mail go.