For about one month,probably since the latest version of Mail or perhaps the one before, any attempt to send Mail fails at initial try. Happens with 10.6.2 and 10.5.8 (different machines). Opening Activity Window and stopping the send puts the message into Outbox, from where the email can be double clicked and then sent successfully. Other emails after that go OK until there is a period of no email activity, and then the hold-up starts again. The Apple Support forums are full of other users having the same problem, so it's not just me. No response from Apple yet ! Grateful to hear of any solution that fixes the problem.

When you say it happens on different machines, is this on the same network or the same account you are sending to? First thing I would do is talk to your ISP to check settings and see if there is anything going on at their end.

Phil

Different locations - home v work - Static IP at former (Intel iMac Snow Leopard), behind Firewall at latter (PPC iMac Leopard). Logic tells me that if it works at second try, without any connection parameters being altered, then it can't be the ISP. And, the Apple Forums postings suggest it is a widespread problem. All my email accounts use XTRA for the smtp, except for me.com. Problem same for all accounts. Ergo, must be the application. Hoping there are others out there with same.

Well I had an issue like that years and years ago and it was my ISP settings...but from different locations you can pretty much scrap that I think. I'm stumped sorry.

Phil

Yes I am having the exact same problem, and am also with Xtra (for my sins).
Have been meaning to post about it for a couple of weeks, but was kind of hoping it would fix itself! Havent had a chance to look at forums about it but interesting to hear it is happening to a few people.
Can't help with any solution though sorry but will keep following this topic in case someone can

Since Xtra stopped running their own mail servers and run via. Yahoo in Australia there have been no end of problems with both SMTP and POP email.
Thier mail servers randomly drop incoming emails for no particular reason. I often have this when sending email to my brother-in-law but sending the exact same email again will make it go through.
There are similar issues with their SMTP servers ie. first send attempt won't work, second one will.
One thing that may be worth checking is if their new SMTP servers support authenticated SMTP over a secure port. This will mean making some changes to the way your SMTP mail sends (usually appending @xtra.co.nz to the username and changing the port to a secure one that they list) - if this is an option use it and it may well cure all of your problems.
Also take note that Xtra like most modern ISPs will not allow you to send email via. their SMTP servers if you are not using them as the ISP at the time. ie. is you are logged in to a corporate network, or an alternative ISP, you won't be able to use their SMTP servers.

I hope that some of this may be of use.

Cheers

Jamie (aka. Dragonfire .... wishing I could change my username somehow)

You should all get yourself a free NZMac.com Gmail account

www.nzmac.com/email-accounts.html

I've now moved all my email on to that account.

Phil

Yep, they work well Phil. I don't use mine for a lot of stuff but in all honesty anything has to be better than ISP based email!

Just a follow up note to say that the problem has stopped, without any change to settings on either of my computers. Ergo, XTRA has responded to our notifications and fixed something at their end.