Problem sending pop email

Question

I have a problem sending (not receiving) pop email.
I am connected directly to my ISP (virgin.net, part of virginmedia.com) on adsl – (ie not trying to connect via another isp) - sharing the internet connection wirelessly via a modem/router to 2 Macs (macbooks), a Vista laptop and wiredly to an XP desktop.
The problem only happens with the Macs, not the Windows machines. One of the Macs is running Tiger with mail 2.1.3, the other Leopard with mail 3.2. Both are affected.
The problem only arises when trying to send longer messages (a few paragraphs - not MB). There is no problem sending short (one or two word) messages. I'm not sure where the cutoff comes.
What happens is that the messages are simply timed out, after a lengthy attempt to send. The error message is generally
‘The server response was: 4.4.2 omf09.hostedemail.com Error: timeout exceeded ‘
but sometimes (more recently, perhaps as a result of all the fiddling I describe below)
‘An error occurred while delivering this message via the SMTP server "(null)" ‘
This started on Friday 30th May. That day we woke up to find we were unable to receive email either. Looking at the mail accounts, I saw that the (incoming) authentication had spontaneously(?) changed from "password" to MD5 challenge response. Since returning it to password, we've been able to receive mail on both machines.
We only noticed the problem with sending a few days later as we hadn’t tried to send any longer messages; so it’s not absolutely certain that it’s related – but it seems likely.
We can send pop email from our googlemail accounts. We can also use virgin’s webmail with no problems.
This is what I’ve tried to resolve the problem:
checked that the server etc settings are configured according to Virgin’s instructions at
http://www.virginmedia.com/help/email/set-up-pop-email.php#OS_X103
(on the advice of support there) deleted one of the affected accounts (and also removed the smtp server from the server list) and recreated it. No effect.
Installed Thunderbird and set up the same account. Same problem there.
Used Connection Doctor – shows connections to all servers as green
Rebooted the modem/ router, and both machines
Repaired permissions
Nothing seems to help.
I’ve done all this on the Tiger mac, on the theory that once I find the solution there is will also apply to the Leopard one ie that it’s not a glitch of some recent Leopard update.
Because the Windows machines (and webmail) work fine, Virgin clearly think that this is simply a Mac problem. I suspect that they have changed something in their setup, as it seems unlikely that it would otherwise affect two Macs running different versions of OSX in the same way.
I’ve only recently persuaded my wife to switch to a Macbook after her experience of Vista so this is not only annoying but embarrassing!
David

Answer 1

I have a Mac and have had the same problem with Virgin – I have been unable to send emails of more than about 300 words, or any replies or attachments, since May 30, the day Virgin “improved” their email services. Receiving emails and using webmail are not affected. Virgin’s helpline has been totally unhelpful, refusing to accept that it has anything to do with them or that some other Mac users are affected in the same way. Their fault team insists it’s a problem with my computer. I have O.S. 10.5.3 Leopard, having just upgraded, but the problem occurred when I was still on O.S. 10.4. Tiger. My email program is Entourage (which Virgin’s helpline hasn’t even heard of!). When the problem first occurred, I wasn’t able to send any emails, but by changing the Accounts advanced settings to what Virgin recommended when I phoned them, I could at least send short emails. (Their announcement of the email changes said, “Don’t worry, you don’t have to do anything.”) Virgin are trying to put a huge spin on this shabby treatment of Mac customers by saying, “We’re doing lots of things to make your experience with us even better” – but with friends like this, who needs enemies?