Mailing with SMTP doesn't work anymore, 10.6.2

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!

Very interesting post.
It doesn't speak directly to my issue with very poor performance connecting to exchange 2007, but I think there is definitely something screwy with the way that mail.app handles the smtp entries.

For two of my users (so far) mail was flowing ok - then Send started to fail with the usual non helpful dialog about smtp.

As I looked closer, the Exchange smtp entry was MIA.
After I manually created it, mail again flowed ok.

Now I have an issue where large emails can't be sent, or even forwarded.
It's not a size issue, as there is no size limit on attachments on my server.
And this shouldn't even matter when forwarding via Exchange, as the mail is already on the server, and is merely being copied from one box to another.

That's further demonstrated by the fact that I was able to pop open Safari, log into OWA, and forward the message instantly.

It looks to me that mail.app doesn't really implement the Exchange protocols properly.

Johnjohn77, your symptoms matched mine almost exactly. My orange broadband connection was working fine up until the beginning of Jan 2010 and I had no problems upgrading from Tiger to Snow Leopard, email worked fine throughout.
However, at the beginning of January everything went pear-shaped. The only thing I can attribute my problems to, was a significant Micorsoft update (I have most of the Office suite on my Mac). At the end of the update my Mac was left unusable, it would boot to the desktop then hang. I had to re-install Snow Leopard from scratch, which worked fine in ALL respects except that my email accounts would not send outbound emails via the default server smtp.orangehome.co.uk server.

I therefore read your post with interest and followed your instructions almost to the letter. I attempted to cut straight to the chase by going to the advanced tab and setting a custom port of 587 (no ssl checked) but no joy. Then, just for fun I tried custom port 25 and, hey presto, it started working. Doesn't make any sense to me, just glad it's fixed.

Hope this helps someone in orange broadband **** 😉

I am suddenly unable to send email though Mail.app 4.2 via any SMTP server while logged onto any network. I've been reading on message boards about ISPs blocking port 25, but this problem occurred suddenly EVERYWHERE, so it seems like it has to be a Mail.app/Snow Leopard fail. I have tried Thunderbird, just to see if the problem was network related, and Thunderbird works fine (on every network). I like the Mail.app interface, and integration with MobileMe and Mac OS X, and I'd rather not switch, but it's looking like I will have no choice but to switch (and probably cancel MobileMe as well). Has anyone ever resolved this?

Hi
I am having the same problem. Up until this week I could send mail through the Gmail SMTP server just fine (MBP, Snow Leopard 10.6.2), this week it just stopped. Nothing's changed, it just stopped working.

I thought it might be a gmail/Mail interaction thing but can't see what's happened because I haven't changed any settings.

Receiving gmail is no problem, just sending. I'm very, um, unhappy about it.

Now I cannot get Thunderbird to work either. It's starting to seem more like a general Snow Leopard fail. I didn't think anything could make me want to go back to Windows, but having a $2,500 computer that cannot even send email...

Same problem here - but I'm with Free in France. Have played with every variation I can think of!!!

To add to this....

My smtp server is permanently "offline" and when the connection doctor fails, it recommends checking info in account preferences but I know they are correct?????

I'm having the same problem since this morning, I'm on 10.6.4, everything worked fine yesterday and when i switched on the computer this morning....no outgoing emails....all my settings are 100% correct and haven't been changed in months.....hits is bloody frustrating :/

Same thing for me on 10.6.4

is there a way to downgrade from an upgrade ? if that makes sense ? like revert the system to 10.5 or something ? i tried time machine but that didnt help :/

how i just got around the issue:

- reset Apple Mail via Time Machine a month back.
- set SMTP port manually to 25

and it seems to work.....for now.

Although I have been using 10.5.8, I was setting up my daughter's new laptop which is running 10.6.4 and was running into some SMTP problems. The solution that I used is one that I have used for several years myself which allows you to use localhost (or 127.0.0.1.... your own machine) as the sendmail server. You download an application on your machine from a company called Loapowertools that provides a free service directing your localhost mail to a secure server (I use one of their paid services since I have a large amount of email). I found out about the company (http://www.loapowertools.com) by working with them in their early days.

I can also confirm that Loa Powertools works really well for sending email. I had problems sending when on the road and downloaded and installed Powertools and haven't had a problem since. This had to do with my ISP blocking my SMTP port while using other ISP providers (including at my work). If you can't solve your problem - I'd definitely give Powertools a try!