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Authenticated SMTP connection fails from OSX 10.10 Yosemite

u123072
Grafter
Posts: 41
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Registered: ‎30-05-2011

Authenticated SMTP connection fails from OSX 10.10 Yosemite

Is anybody else having problems connecting securely to relay.plus.net (using account+mailbox and password, No SSL, Port 25) from OSX 10.10 Yosemite Mail App?
The smtp server is showing up as Offline when the credentials are completed.
I have a Mac Mini at my home address. If I "allow insecure authentication" I can send mail - but I don't want that.
I have no problem sending mail using Thunderbird from a Win7 machine using the same credentials from the same connection.
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11 REPLIES 11
jelv
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Re: Secure SMTP connection fails from OSX 10.10 Yosemite

You could try port 587.
jelv (a.k.a Spoon Whittler)
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u123072
Grafter
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Registered: ‎30-05-2011

Re: Secure SMTP connection fails from OSX 10.10 Yosemite

I tried port 587 with the same results.
I also tried my primary plusnet account with no mailbox - no difference either
avatastic
Grafter
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Re: Secure SMTP connection fails from OSX 10.10 Yosemite

Secure SMTP sounds like you are trying to connect with TLS?
Plusnet don't support encryption on their mail servers.
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u123072
Grafter
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Registered: ‎30-05-2011

Re: Authenticated SMTP connection fails from OSX 10.10 Yosemite

Sorry, I meant authenticated, as in a plain password and username sent to the server.
I just wanted to replicate the settings I use with Thunderbird \ Win7.
RPMozley
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Re: Authenticated SMTP connection fails from OSX 10.10 Yosemite

Does it say "allow insecure authentication" as you mentioned in the first post?
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u123072
Grafter
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Registered: ‎30-05-2011

Re: Authenticated SMTP connection fails from OSX 10.10 Yosemite

There is only an option for the IMAP server called "Allow insecure authentication". I have "Password" as the IMAP authentication method.
However for the SMTP server there is just a list of authentication options to choose from : None, TLS, GSSAPI, NTLM, MD5, Password.
When "None" is selected I can send mail, when "Password" is selected and I complete my credentials, mail will not send.
spraxyt
Superuser
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Registered: ‎06-04-2007

Re: Authenticated SMTP connection fails from OSX 10.10 Yosemite

Since you are experiencing "SMTP server showing up as offline" does one of the fixes mentioned by OSXDaily here help?
David
dvorak
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Re: Authenticated SMTP connection fails from OSX 10.10 Yosemite

you could always install thunderbird on your mac if you want to keep the same experience as win.
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u123072
Grafter
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Registered: ‎30-05-2011

Re: Authenticated SMTP connection fails from OSX 10.10 Yosemite

Quote from: spraxyt
Since you are experiencing "SMTP server showing up as offline" does one of the fixes mentioned by OSXDaily here help?

Thanks for the link, I had already found this advice and I have now solved the problem.
It seems the configuration dialogue boxes in Mac Mail do not include the option for allowing unsecured authentication to SMTP servers.
The option is however included in the plist config text files for the Mail app. So a bit of text editing solved the problem.
u123072
Grafter
Posts: 41
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Registered: ‎30-05-2011

Re: Authenticated SMTP connection fails from OSX 10.10 Yosemite

Quote from: u123072
It seems the configuration dialogue boxes in Mac Mail do not include the option for allowing unsecured authentication to SMTP servers.

OSX 10.10.1 has just been release and lo and behold the configuration dialogs now have a check box for this.
spraxyt
Superuser
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Re: Authenticated SMTP connection fails from OSX 10.10 Yosemite

Thanks for that feedback. Smiley
David