OSX 10.6 Mail SMTP fail (fine on Entourage, iPad and iPhone)

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Level 1

133 points

OSX 10.6 Mail SMTP fail (fine on Entourage, iPad and iPhone)

Weird one here.

My SMTP server is failing to verify from Mail 4.6 (1085) running under OSx 10.6.8 on a MacBook Pro 1,1 2.16ghz 2gb ram.

Installed on the same computer is Entourage (12.0.0) which works fine, as does my iPhone and iPad. All connected to the same router via wifi.

Obviously I've gone over the settings with a toothcomb, and they are identical. Just for reference here they are:

server: smtp.123-reg.co.uk

authentication: password

user name: <email address>

pw: secret!

port: 465 (have tried 25 and 587 as well)

ssl: on (tried off with all above ports)

Anybody got any bright ideas as to why Mail doesn't want to play ball? Anything else I should be checking?

Thanks,

Dom

Posted on Aug 23, 2013 3:05 AM

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Answer 1

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BGreg

Level 6

17,552 points

Aug 23, 2013 4:12 AM in response to Dom Caz

In mail, have you clicked on Window on the menu bar and then Connection Doctor? That will usually tell you where the issue is, and if you click on the problem statement, take you to where you can fix it.

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Answer 2

Dom Caz Author

Level 1

133 points

Aug 24, 2013 5:21 AM in response to BGreg

I hadn't tried connection doctor, but it's led me to some more info about my problem, sent me to some more websites and forums and ultimately a solution...

Connection doctor was not giving me much info (1 line saying it was trying to connect), so I plumbed all the email settings into Mail 6.5 (1508) running under 10.8.4 on another Mac, I get the same issue (and the same positive result with Outlook 14.3.5), but at least connection doctor there gave me a lot more info.

The clue was this from connection doctor:

WROTE Aug 24 11:54:51.854 [kCFStreamSocketSecurityLevelNone] -- host:smtp.123-reg.co.uk -- port:25 -- socket:0x7fe58fb2af10 -- thread:0x7fe58b127840

EHLO unknown-e4:ce:8f:50:34:ba.home

READ Aug 24 11:54:51.901 [kCFStreamSocketSecurityLevelNone] -- host:smtp.123-reg.co.uk -- port:25 -- socket:0x7fe58fb2af10 -- thread:0x7fe58b127840

501 Syntactically invalid EHLO argument(s)

A lot of reading of forums (http://business.forums.bt.com/t5/Email/email-on-Mac-problem-sending/td-p/46630/p age/2) led me to realise this was my BT Home Hub 3, Mail and the 123-reg smtp server having an incompatibility.

I changed the name of my computer in sharing prefs to a simple name with no spaces and punctuation, made sure the new name was updated in the hub, restarted both and bingo we're working.

The hub was suffixing to wifi mac id of the Mac with .home and this was failing the EHLO/HELO authentication.

Anyway, problem solved. Thank god!!

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