Cannot send mails using office365 smtp server
-
From your earlier post it looks like the connection is successful with STARTTLS enabled. But the authentication is failing.
"2) Enable STARTTLS -> Error: 504 5.7.4 Unrecognized authentication type (takes longer to fail)"
Google that error code and message string and you'll find lots of information that may point you in the right direction.
-
Hi,
Yep, looked that error message up, and contacted (Microsoft) Exchange Online support. The one open question they have, that I can't seem to find … is pfSense using TLS v1.1 for the email send? They think that's the problem, but I can't confirm the version.
Does anyone happen to know?
Thanks!
-
The problem is not exactly with Office 365 Mail servers - rather with Exchange (and potentially other mailservers as well):
While researching the issue that pfSense won't send using our Exchange 2010 Server I found the underlying cause for it.
pfSense (our version is 2.1.5-RELEASE, but I guess other versions are also affected) seems to support several Authentication mechanisms for SMTP (at least that's what I gathered from the various files), but it ALWAYS uses "PLAIN".
If the E-Mail-Server does not support "PLAIN", E-Mail-Notifications will fail - typically with "Authentication mechanism not supported".
Now - guess what … Exchange does support plaintext-logins when configured correctly, but only using the method "LOGIN" ...The culprit is in File /etc/inc/notices.inc , Line 324:
// Use SMTP Auth if fields are filled out
if($config['notifications']['smtp']['username'] &&
$config['notifications']['smtp']['password']) {
$smtp->authentication_mechanism = "PLAIN";
$smtp->user = $config['notifications']['smtp']['username'];
$smtp->password = $config['notifications']['smtp']['password'];if I change this line to
$smtp->authentication_mechanism = "LOGIN";
I can send e-mail-notifications via our Exchange-Server. But I guess this will break Notifications for other mailservers.IMHO there are two ways to fix this behaviour (sadly both beyond my pfSense/php-Knowledge):
- get the list of supported auth-mechanisms from the server (after doing TLS if necessary - some servers offer plaintext-login only after a secue session was established) and "match" with local supported mechanisms (perhaps the smtp-class allows this already)?
- allow the admin to select the auth-mechanism from a list of mechanisms supported by pfsense
-
Hi,
Very cool finding - awesome! I'll give it a try (manual change), but also … why not start with 2), try 1) later? At least 2) would get things up and running.
Thanks!
-
I had the same problem Authenticating but with Symantec Messaging Gateway (SMG). Changing PLAIN with LOGIN solve it. Thanks!
The problem is not exactly with Office 365 Mail servers - rather with Exchange (and potentially other mailservers as well):
While researching the issue that pfSense won't send using our Exchange 2010 Server I found the underlying cause for it.
pfSense (our version is 2.1.5-RELEASE, but I guess other versions are also affected) seems to support several Authentication mechanisms for SMTP (at least that's what I gathered from the various files), but it ALWAYS uses "PLAIN".
If the E-Mail-Server does not support "PLAIN", E-Mail-Notifications will fail - typically with "Authentication mechanism not supported".
Now - guess what … Exchange does support plaintext-logins when configured correctly, but only using the method "LOGIN" ...The culprit is in File /etc/inc/notices.inc , Line 324:
// Use SMTP Auth if fields are filled out
if($config['notifications']['smtp']['username'] &&
$config['notifications']['smtp']['password']) {
$smtp->authentication_mechanism = "PLAIN";
$smtp->user = $config['notifications']['smtp']['username'];
$smtp->password = $config['notifications']['smtp']['password'];if I change this line to
$smtp->authentication_mechanism = "LOGIN";
I can send e-mail-notifications via our Exchange-Server. But I guess this will break Notifications for other mailservers.IMHO there are two ways to fix this behaviour (sadly both beyond my pfSense/php-Knowledge):
- get the list of supported auth-mechanisms from the server (after doing TLS if necessary - some servers offer plaintext-login only after a secue session was established) and "match" with local supported mechanisms (perhaps the smtp-class allows this already)?
- allow the admin to select the auth-mechanism from a list of mechanisms supported by pfsense
-
Hi,
If you don't mind me asking - what are the rest of your settings (like port number, SSL/TLS or STARTTLS, etc.)? Still struggling a bit.
Thanks!!!
-
Got it working! Issue was STARTTLS (and save before Test).
Thanks!
-
This also fixed my issue, many thanks.
-
for this issue I added my account via POP3 and SMTP in outlook 2016 it works fine and also I test it via power shell and It works fine too.
-
E-Mail server: smtp.office365.com
SMTP Port of E-Mail server: 587
Connection timeout to E-Mail server: blank
Secure SMTP Connection: unchecked
From e-mail address: user@example.com
Notification E-Mail address: user@example.com
Notification E-Mail auth username (optional): user@example.com
Notification E-Mail auth password: userpassword
Notification E-Mail auth mechanism: Login
Send Test
Save after successful test -
@bethelcolonyit. Helped in big way. Thank you so much for the poast
-
I know this is old but it was a top search result.
The good news, there are 3 methods:
https://docs.microsoft.com/en-us/exchange/mail-flow-best-practices/how-to-set-up-a-multifunction-device-or-application-to-send-email-using-microsoft-365-or-office-365The bad news: the purple note in section 1 (info on using a login and password) on that page:
"This option is not compatible with Microsoft Security Defaults or multi-factor authentication (MFA). If your environment uses Microsoft Security Defaults or MFA, we recommend using Option 2 or 3 below.You must also verify that SMTP AUTH is enabled for the mailbox being used. See Enable or disable authenticated client SMTP submission (SMTP AUTH) in Exchange Online for more information."
