EmailDiscussions.com  

Go Back   EmailDiscussions.com > Email Service Provider-specific Forums > FastMail Forum
Register FAQ Members List Calendar Search Today's Posts Mark Forums Read
Stay in touch wirelessly

FastMail Forum All posts relating to FastMail.FM should go here: suggestions, comments, requests for help, complaints, technical issues etc.

Reply
 
Thread Tools
Old 21 Dec 2018, 05:17 PM   #1
stvvbkk
Junior Member
 
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?
stvvbkk is offline   Reply With Quote

Old 21 Dec 2018, 11:20 PM   #2
BritTim
The "e" in e-mail
 
Join Date: May 2003
Location: mostly in Thailand
Posts: 2,712
In the advanced tab, ensure the port number for SMTP is 587 and Use SSL is ticked.
BritTim is offline   Reply With Quote
Old 22 Dec 2018, 05:04 AM   #3
xyzzy
Member
 
Join Date: May 2018
Posts: 61
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?
xyzzy is offline   Reply With Quote
Old 22 Dec 2018, 06:39 AM   #4
Terry
The "e" in e-mail
 
Join Date: Jul 2002
Location: VK4
Posts: 2,634
Quote:
Originally Posted by stvvbkk View Post
Does anyone know what might be going on?
I suppose you using the application password
Terry is offline   Reply With Quote
Old 23 Dec 2018, 04:06 PM   #5
stvvbkk
Junior Member
 
Join Date: Feb 2013
Posts: 5
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!
stvvbkk is offline   Reply With Quote
Old 24 Dec 2018, 03:25 AM   #6
mballas
Essential Contributor
 
Join Date: Dec 2001
Location: Denton, TX
Posts: 327
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.
mballas is offline   Reply With Quote
Old 24 Dec 2018, 04:21 AM   #7
BritTim
The "e" in e-mail
 
Join Date: May 2003
Location: mostly in Thailand
Posts: 2,712
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.
BritTim is offline   Reply With Quote
Old 24 Dec 2018, 05:40 AM   #8
mballas
Essential Contributor
 
Join Date: Dec 2001
Location: Denton, TX
Posts: 327
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
mballas is offline   Reply With Quote
Old 24 Dec 2018, 07:25 AM   #9
Terry
The "e" in e-mail
 
Join Date: Jul 2002
Location: VK4
Posts: 2,634
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.
Terry is offline   Reply With Quote
Reply


Thread Tools

Posting Rules
You may not post new threads
You may not post replies
You may not post attachments
You may not edit your posts

vB code is On
Smilies are On
[IMG] code is Off
HTML code is Off
Forum Jump


All times are GMT +9. The time now is 04:44 AM.

 

Copyright EmailDiscussions.com 1998-2013. All Rights Reserved. Privacy Policy