Mailing with SMTP doesn't work anymore, 10.6.2

Question

Hi all,
after reading so many posts regarding Mail and how sending emails doesn't work with 10.6.2, there still seems to be no solution that works for everyone.
After Updating to 10.6.2 I cannot send emails through ANY smtp server.
I also have a windows 7 machine running thunderbird and everything works there.
I tried all suggested solutions,i.e.
1.) I checked connection doctor and everything seems to be fine (including the detailed messages)
2.) I tried all sort of settings, with, w/o SSL, all sorts of ports
3.) I "reset" the keychain
4.) I "reset" Mail preferences by deleting com.apple.mail.plist in library\preferences
still, I can only receive emals but not send. any solutions are greatly appreciated, thank you in advance!

Answer 1

Hi - here is a bizarre solution (possible bug); I hadn't been able to ever send any with my 3 month old MacBookPro through Apple Mail 4.2, similar to what you say. That was under 10.6, 10.6.1 and 10.6.2. I was using my Win PC to send emails, or via Web clients in Safari off the MacBookPro, but finally I reached the time to call Orange UK, my ISP...
I have just had a great experience with their technical support, but the solution reached was NOT logical - let me explain it, perhaps it might work for you.
The logical background is this:
Define an SMTP server; if you have Orange broadband, you HAVE to use theirs (as they block other servers form using the standard ports 25, 465 and 587 - apparently for SPAM reasons, or perhaps they are now required to keep an eye on everything... who knows.
So, in Apple Mail 4.2; we went to the menus, and Mail -> Preferences
highlight any account on the left, and at the bottom of the right hand pane, in the Account Information tab, click and define the SMTP server (click the box, choose Edit server, create an SMTP server - for Orange UK, I had to put in
smtp.orangehome.co.uk
then ensure this is the only SMTP server Apple Mail uses, by checking the box in Account Information tab, Use only this server.
Go back into Advanced tab, and here is where the logic starts to end...
To recap: Mail -> Preferences -> Click on the Orange SMTP server button -> click "Edit SMTP server list..." (again) and go to the Advanced tab.
In this tab are two main choices:
Use Default Ports (25,465,587)
Use Custom Port (by default this is a completely blank box)
Now, logic dictates that you would leave the 'use default ports' option checked, then try all other manner of parameter changes. But, we tried forcing 25 into Use Custom Port.
Use Custom Port - 25
but this too didn't work.
Then I tried, for fun:
Use Custom Port - 587 (no SSL checked, and Authentication - none; again illogical as 587 should be an SSL port, as is 465)
And... suddenly my mail sent, for the first time ever!
mmm... When I looked again at this tab, though, the Use Custom Port box had reverted to saying...
Use Custom Port - 25 (???) but who cares, it worked. Why it didn't work the first time, I have no clue.
NB Between each try, I quit Apple Mail, deleted my test Outbox sending messages, and essentially made sure nothing was trying to be sent. This was between each 'attempt'. This might have been an important thing to do, but I don't know.
So, my best guess is to just try forcing the Custom Port to be 25, then 587... and keep trying. My emails still take about 5-10 secs to send, rather than almost immediately like they used to before I started with Orange Broadband (which I am, interestingly, finding to be a faster service than my previous ISP, and as yet, appears just as reliable...) It’s all so Weird! It’s the only thing that has really annoyed me with this my first Mac, so that’s good going!
Good luck!