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Old 21 Dec 2018, 05:17 PM   #1
stvvbkk
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Join Date: Feb 2013
Posts: 5
"Cannot send messages using the server" in Mac OS X Mail

In the OS X Mail app on my Macbook, I can't send messages from my fastmail account. I've tried several times putting in a New App Password from Fastmail. In Mail, I receive messages just fine. When I try to send something, I get the following popup message:

"Cannot send message using the server"
smtp.fastmail.com:xxxxxxxx@fastmail.net

"The SMTP connection to server 'smtp.fastmail.com' failed."

It lists the server in the menu as "smtp.fastmail.com:[myemailaddress]@fastmail.net".

I followed both the automatic instructions and then tried the manual instructions from Fastmail:
https://www.fastmail.com/help/clients/mac.html
https://www.fastmail.com/help/client...il-manual.html

I consulted this Fastmail.com page about "Email client sending issues", which wasn't any help:
https://www.fastmail.com/help/client...ingissues.html

Does anyone know what might be going on?
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Old 21 Dec 2018, 11:20 PM   #2
BritTim
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In the advanced tab, ensure the port number for SMTP is 587 and Use SSL is ticked.
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Old 22 Dec 2018, 05:04 AM   #3
xyzzy
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587? That's for STARTTLS.

Look here for all the server settings and make sure your SMTP settings have port 465 and SSL set. And of course using the app-specific password.

Doesn't mac mail have a "Connection Doctor" menu item which allows you to trace the protocol exchange to pin down exactly what's not working?
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Old 22 Dec 2018, 06:39 AM   #4
Terry
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Quote:
Originally Posted by stvvbkk View Post
Does anyone know what might be going on?
I suppose you using the application password
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Old 23 Dec 2018, 04:06 PM   #5
stvvbkk
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Quote:
Originally Posted by BritTim View Post
In the advanced tab, ensure the port number for SMTP is 587 and Use SSL is ticked.
That did it! I changed the SMTP port from 465 to 587 and kept Use SSL ticked, and now my sent emails are actually sending.

Thanks, all!
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Old 24 Dec 2018, 03:25 AM   #6
mballas
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Quote:
Originally Posted by stvvbkk View Post
That did it! I changed the SMTP port from 465 to 587 and kept Use SSL ticked, and now my sent emails are actually sending.

Thanks, all!
I don't know why but 465 and SSL work on my machine.
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Old 24 Dec 2018, 04:21 AM   #7
BritTim
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Quote:
Originally Posted by mballas View Post
I don't know why but 465 and SSL work on my machine.
Which version of the OS X Mail app? I have seen 465 fail. It seems, on some OS X versions, "Use SSL" is misleading as only TLS is supported.
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Old 24 Dec 2018, 05:40 AM   #8
mballas
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Quote:
Originally Posted by BritTim View Post
Which version of the OS X Mail app? I have seen 465 fail. It seems, on some OS X versions, "Use SSL" is misleading as only TLS is supported.
Mail Version 12.2 (3445.102.3)

MacOS Mojave 10.14.2
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Old 24 Dec 2018, 07:25 AM   #9
Terry
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I found that with some phones you have to tick the 3 boxes IMAP/POP/SMTP when you apply for a new application password.

Well that worked for me anyway.

Last edited by Terry : 24 Dec 2018 at 07:54 AM.
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