Anyone having smtp outgoing mail since Mountain Lion Upgrade?

Talk of the devil, first time in a few weeks that the SSL isue with Gmail is back! Grrr...

can not believe they did not fix this issue with the latest update. thats a joke. i'm back on outlook 😟

Hi HelenCW an o2 mail users on mac mail. Here is the fix:

1.0: First, reset your o2 password for your o2 webmail account

1.1: Go to www.o2.co.uk and login to your online account

1.2: If you have more then one o2 online account and have linked them; unlink them

1.3: Reset your o2 webmail password for any/every o2 webmail account

2: Once you receive confirmation from o2 of your new password log back into your online o2 webmail account and create a new personalised password

3: Check that your new password is working by login out of o2 webmail and then loging back in again using your new password

4: Open mac mail Preferences/Accounts and delete your old o2 mail account

5: Under Preferences/Accounts add ➕ a new account and follow the prompt then click continue; when the faillure message appears click continue

6: On the Pop mail settings page change the pop.o2.co.uk to; mail.o2.co.uk follow the prompt and click continue

7: If asked about Authentication tick the box and enter your full o2 email address and password

8: Do not enter SSL details and if possible change the drop down menu from Password to None on outgoing and/or incoming mail servers, click continue

9: Once complete I selected setup manually and double checked the details by going back through each stage of the setup and again clicking on continue right through to the end review and tick the Take Online box

That should be it!

I took me many attempts to get it right as I have more then one o2 webmail account; forgive me if I missed a stage or got the wrong order, but I'm not troubling my settings again now that I'm up and running, however you'd be pleased to know it's now all up and running as normal.

Hope this helps.

I have found a couple of solutions that worked for one of my accounts but not the other. Note that my accounts are POP.

Solution #1: Edit Accounts.plist directly

1. Quit Mail

2. Make a backup of the ~/Library/Mail/V2/MailData/Accounts.plist file.

3. Edit the ~/Library/Mail/V2/MailData/Accounts.plist file manually in a text editor.

4. Find the offending setting(s) that differ from the correct setting(s) and correct them (note - this is an XML file so you have to understand markup languages - but it is pretty straightforward)

5. Start Mail and see if it works!

Solution #2: Delete all your accounts, restart Mail, and start over:

1. When you setup the account, enter your name and email address.

2. When you hit Continue it will try to contact your server, and in my case, will fail or will complain about a certificate issue - if so - hit "Cancel".

3. You will then get another config window where you can enter you POP account info.

4. When you hit Continue - it will try to login to your POP server - regardless of what it says, hit Continue and enter your correct authentication options and Continue.

5. On the next screen, enter your SMTP server info and hit Continue. Hopefully it will complain about something and present you with an option to Setup Manually - anytime you get this option, select Setup Manually.

6. Enter your outgoing server authentication setting.

7. It will now show you all of the settings you have entered, with a checkbox re: whether you want to activate the account - make sure that is NOT checked.

8. Continue and then Mail will start and show you your new account

9. Edit the settings of the new account you just created and make sure the settings are correct (e.g. the setup above never lets you specify whether to use default ports or not - go there and make sure setting is correct).

10. Bring the account online and both the POP and SMTP should work. The key here seems to be the option that says "Setup Manually" - but I can't figure out how to force that option in all cases.

Mountain Lion Mail definitely has a bad bug. I've tried changing various settings and then examining the contents of Accounts.plist (in ~/Library/Mail/V2/MailData) and the results are discouraging - there doesn't seem to always be a co-relation between what you put in the config GUI and what shows up in Accounts.plist. The fact that using the "Setup Manually" option (when you can get it) seems to result in an SMTP account that works, while the normal method doesn't, shows there is a bad bug somewhere. I think someone at Microsoft has infiltrated Apple.

Second update since the release of mountain lion and mail is still not working as it should. I wonder what has to be done now, stop working with apple? I mean "mail" is probably the most used program so I dont get it why they dont care. Im not able to send any email with my apple machines.

I tried editing the server list but went round and round until I got a little help from others.

Go to System Prefs/iCloud and unclick Mail.
Go to Mail prefs and add accounts here...enter the email address and password for each of your accounts.
Ignore all the incoming and outgoing server fields. iCloud will do that for you later.

Once your email accounts are entered on your computer, go to your mobile devices (iPhone/iPad/etc) and
make sure those accounts are enabled there.

And match the on off switches for Mail, Notes, etc....so that all your devices are matched up.

Then go back to System Prefs/iCloud and confirm that Mail is checked.
At this point your Mail should be repopulating and all is right with the world.

My Mac would never finalize the Mail setup until my mobile devices were all in agreement.
Then it was automatic. I never had to worry about incoming and outgoing server fields at all.

This will save you much needless frustration & worry.

Can I ask how you did a set up without adding an incoming mail server? When I try to set up a new mail account, it won't let me set one up without an incoming server.

I would like to try your suggestion because I have tried everything else to no avail.

I have been without outgoing mail from my business domain for weeks and have spent hours trying to resolve this, using advice from these forums and from my ISP. No luck. My email broke when I installed Mountain Lion or when I set up iCloud. I can't be sure which, but it was definitely one or the other.

This is very frustrating and I welcome a fix.

OK, thanks all for this thread, I had the exact same problem and changing to port 587 worked for me as well. Why does Apple do this?

FWIW... Problem fixed for me (and some commentary)

I waited for a little while until installing 10.8.2, and everything worked except outgoing POP (SMTP) mail.

I called Apple support yesterday with the intention of adding my 'weight' to what I presumed was an outstanding problem.

Support's demeanour was not in any way defensive, and I did NOT detect that this was something that was widespread.

I got escalated to level 2, and the support person tried several things, and then got me to delete the outgoing server in preferences, exit Mail, restart Mail, add the outgoing server back, and its worked since.

I realize this may not work for many of you, but I suggest giving it a try.

Support admited there may some issue that happens during the 10.7.X to 10.8.X upgrade.

Good luck.

I gave up on O2 smtp (mountain l) and now simply use my me.com smtp; works perfectly. So it doesn't sound like an Apple prob to me. Mind you, O2 is one of the most irritating things in my life. O for the day my contract runs out!

I have IMAP and I used a variation of momorewin solution.

1. open Mail

2. change the file name of ~/Library/Mail/V2/MailData/Accounts.plist

to ~/Library/Mail/V2/MailData/Accounts.plistBAD

3. Edit accounts SMPT server list using Apple Mail Preference

4. Exit and save Apple Mail Preference

5. Quit and Restart Apple Mail

6. It works!

Hi there, I had this problem and tried every suggestion I could find and got nowhere. Anyway, quite by accident, I restarted my Thomsom Gateway which is normally on 24/7 and whoosh, literally, the sent mail was working again. My SMTP has gone offline a couple of times since and restarting my Thomson Gateway has fixed the problem straight away. Perhaps that might work for some of you. Oh and I also force quit my mail and reopened it though not sure that that really mattered.

Regards, Robyn.

I had this problem...deleted the SMTP account and recreated it, but still had trouble. SSL is something I expect to be problematic for me because I own my own domain but host it at Dreamhost, so certificates aren't going to match.

I noticed the UI wasn't letting me unselect SSL. That is to say, I would uncheck the box, and then it would quickly run some network activity in Connection Doctor, and recheck the box for me.

I tried unchecking the box and then quickly closing it before Mail had a chance to change the setting on me (I suppose I could have unplugged the network cable instead). That worked, and not I can send mail again.

I have this problem very often and it is totaly random and very anoying !!

today looking at the mail app configuration file on my macbookair, of my 3 gmail accounts the only that I was having problems was the one that was not using the port 587, so instead of having the mail app choose the port between the 3 options there, I manualy changed to PORT 587 and it has been working since. I hope that helps

That helped! Check the connection doctor. Maybe try inserting your password again too... That is what did it for me.