XF 1.5 Email Transport Method SMTP errors (connection timed out, invalid auth)

[Kay0501]

My old SMTP settings got the Connection timed out error so I updated the new server address and got the Invalid authentication (you can only send From) error. I could log in with the updated config on Outlook.

Spoiler: Old

Request State
Stack Trace
Error Info
Zend_Mail_Protocol_Exception: Email to X@Y.com failed: Connection timed out - library/Zend/Mail/Protocol/Abstract.php:277 Generated By: X, Tuesday at 10:20 PM
#0 /var/www/vhosts/vnsharing.vn/httpdocs/library/Zend/Mail/Protocol/Smtp.php(167): Zend_Mail_Protocol_Abstract->_connect('ssl://s9-singap...') #1 /var/www/vhosts/vnsharing.vn/httpdocs/library/Zend/Mail/Transport/Smtp.php(216): Zend_Mail_Protocol_Smtp->connect() #2 /var/www/vhosts/vnsharing.vn/httpdocs/library/Zend/Mail/Transport/Abstract.php(348): Zend_Mail_Transport_Smtp->_sendMail() #3 /var/www/vhosts/vnsharing.vn/httpdocs/library/Zend/Mail.php(1194): Zend_Mail_Transport_Abstract->send(Object(Zend_Mail)) #4 /var/www/vhosts/vnsharing.vn/httpdocs/library/XenForo/Mail.php(175): Zend_Mail->send(Object(Zend_Mail_Transport_Smtp)) #5 /var/www/vhosts/vnsharing.vn/httpdocs/library/XenForo/Mail.php(152): XenForo_Mail->sendMail(Object(Zend_Mail)) #6 /var/www/vhosts/vnsharing.vn/httpdocs/library/XenForo/Model/UserConfirmation.php(153): XenForo_Mail->send('X@Y...', 'test test test') #7 /var/www/vhosts/vnsharing.vn/httpdocs/library/XenForo/ControllerPublic/Register.php(424): XenForo_Model_UserConfirmation->sendEmailConfirmation(Array) #8 /var/www/vhosts/vnsharing.vn/httpdocs/library/UserEss/ControllerPublic/Register.php(68): XenForo_ControllerPublic_Register->actionRegister() #9 /var/www/vhosts/vnsharing.vn/httpdocs/library/XenForo/FrontController.php(351): UserEss_ControllerPublic_Register->actionRegister() #10 /var/www/vhosts/vnsharing.vn/httpdocs/library/XenForo/FrontController.php(134): XenForo_FrontController->dispatch(Object(XenForo_RouteMatch)) #11 /var/www/vhosts/vnsharing.vn/httpdocs/index.php(13): XenForo_FrontController->run() #12 {main}
array(3) { ["url"] => string(38) "https://X/register/register" ["_GET"] => array(0) { } ["_POST"] => array(16) { ["username"] => string(0) "" ["01ae63c40f61aba6ec62fad9317a43c3"] => string(14) "test test test" ["544ed55f1b1927b5da3cbf35446fd4fc"] => string(19) "X@Y.com" ["password"] => string(8) "********" ["9de9e4e8185b2de20064c33a09973bc3"] => string(0) "" ["3b423651b54ddcc0c48ad87a738e0abd"] => string(0) "" ["dob_month"] => string(1) "0" ["dob_day"] => string(0) "" ["dob_year"] => string(0) "" ["90a5be204b37e43be27f93994cb4aa50"] => array(1) { ["ngnhywm"] => string(0) "" } ["custom_fields_shown"] => array(1) { [0] => string(7) "ngnhywm" } ["5fa40f28f876066fd769c11907195c37"] => string(12) "Asia/Bangkok" ["g-recaptcha-response"] => string(612) "03AEkXODAlU0nFSVqr5oHs7fUG4x5Y_UWZiqyUlzV-4hDLFkkagXUpkNHcip1FvyYDS3v_mWyOe-5jEwfU9NJQp19tX4rDQbyfQN_oMEt9Xohjbs1jTN4X0OB8sH-xj7rzFgq40-sLMP7DngyloEaAcdm5abnyB9NNKX4Cy4mfc0nLM7Iq341hh4SRpeJhxJq-uGHxtH3PrEj6kk3AA48DTZlN7xF5-k7XGXvNHexmH8PS9jTofhpZRajSZXTFeTCF0YoF6KZGPj8XH3ym7YN5Ip7vCvqNJ7Lycjr3lzYgiBd_Q9yU1ivIqsPrtVPKfRWSJqAZzNYo-4oa6OCojTcyczJRDCxN71gTOPR-gY5-KQOwSdoGdTbbhzGW4irMaOUXDSJ4BKfjQwJDiP1GtMnoq6AQ9uIYcNQysPltV1_lIlqfIqvrNK7H83G0s6hxr63AvUVUF9KawhgN2HwZcOpBxQ_f4oYf3YEYUAO_sR1lp7T2mAZ15B8Oq2ezjeWX1a774VLC9SS-cWCORGTIXmuff-Q7-E8lxLpQz1-jBWN0R3YeIQpBcbum32bnYnTM6r1p2XQ8nBK-9tIkdT7xvl5eM6cM5b-vR_7P6Q" ["agree"] => string(1) "1" ["_xfToken"] => string(8) "********" ["reg_key"] => string(32) "4caac6b3aa20804328eaef5202f4bc42" } }

Spoiler: Updated

Spoiler: Email config

Request State
Stack Trace
Error Info
Zend_Mail_Protocol_Exception: Email to X@Y.com failed: Invalid authentication (you can only send From:contact@v.......) - library/Zend/Mail/Protocol/Abstract.php:431 Generated By: X, Thursday at 3:52 PM
#0 /var/www/vhosts/vnsharing.vn/httpdocs/library/Zend/Mail/Protocol/Smtp.php(324): Zend_Mail_Protocol_Abstract->_expect(250, 600) #1 /var/www/vhosts/vnsharing.vn/httpdocs/library/Zend/Mail/Transport/Smtp.php(232): Zend_Mail_Protocol_Smtp->data('Subject: =?utf-...') #2 /var/www/vhosts/vnsharing.vn/httpdocs/library/Zend/Mail/Transport/Abstract.php(348): Zend_Mail_Transport_Smtp->_sendMail() #3 /var/www/vhosts/vnsharing.vn/httpdocs/library/Zend/Mail.php(1194): Zend_Mail_Transport_Abstract->send(Object(Zend_Mail)) #4 /var/www/vhosts/vnsharing.vn/httpdocs/library/XenForo/Mail.php(175): Zend_Mail->send(Object(Zend_Mail_Transport_Smtp)) #5 /var/www/vhosts/vnsharing.vn/httpdocs/library/XenForo/Mail.php(152): XenForo_Mail->sendMail(Object(Zend_Mail)) #6 /var/www/vhosts/vnsharing.vn/httpdocs/library/XenForo/Model/UserConfirmation.php(153): XenForo_Mail->send('X...', 'test test test') #7 /var/www/vhosts/vnsharing.vn/httpdocs/library/XenForo/ControllerPublic/AccountConfirmation.php(108): XenForo_Model_UserConfirmation->sendEmailConfirmation(Array) #8 /var/www/vhosts/vnsharing.vn/httpdocs/library/XenForo/FrontController.php(351): XenForo_ControllerPublic_AccountConfirmation->actionResend() #9 /var/www/vhosts/vnsharing.vn/httpdocs/library/XenForo/FrontController.php(134): XenForo_FrontController->dispatch(Object(XenForo_RouteMatch)) #10 /var/www/vhosts/vnsharing.vn/httpdocs/index.php(13): XenForo_FrontController->run() #11 {main}
array(3) { ["url"] => string(48) "https://X/account-confirmation/resend" ["_GET"] => array(0) { } ["_POST"] => array(5) { ["_xfToken"] => string(8) "********" ["_xfConfirm"] => string(1) "1" ["_xfRequestUri"] => string(18) "/register/register" ["_xfNoRedirect"] => string(1) "1" ["_xfResponseType"] => string(4) "json" } }

 

[ENF]

Are you sending email out through the Outlook email service? (you mentioned that the credentials work for Outlook login..)
If so, their technical docs state that port 587 is used for their SMTP handling. (They also require TLS per the same docs)

Either way, it's not going to be an issue on the XF side. You'll need to assure that credentials are correct. You will also need to make sure you are in compliance with the proper configuration required by your upstream email handler. (Whomever is controlling the SMTP service)

 

[Kay0501]

Hi, thank you for taking a look.

Are you sending email out through the Outlook email service? (you mentioned that the credentials work for Outlook login..)

I tried sending an email from Outlook and it worked if that's what you're asking.


Here's the outgoing settings:


I copied and pasted the password from outlook to the xenforo settings just to be sure again.
Port 465 - SSL: same Invalid authentication (you can only send From) error as above

 

[TPerry]

If so, their technical docs state that port 587 is used for their SMTP handling. (They also require TLS per the same docs)

This is what you were told

I copied and pasted the password from outlook to the xenforo settings just to be sure again.
Port 465 - SSL: same Invalid authentication (you can only send From) error as above

This is what you replied... notice anything different.. you know, like a different port number?

POP, IMAP, and SMTP settings for Outlook.com - Microsoft Support

Learn more about the POP, IMAP, and SMTP settings for Outlook

support.microsoft.com

Also is your sending address in XF configured to be the same as the actual email address you are logging in with? Sometimes those free providers don't allow you to "send" mail as another user through them (say something like no_reply@yourdomain.com and your Hotmail/Live/Outlook login is somethingelse@outlook.com).

 

[Kay0501]

This is what you were told

This is what you replied... notice anything different.. you know, like a different port number?

POP, IMAP, and SMTP settings for Outlook.com - Microsoft Support

Learn more about the POP, IMAP, and SMTP settings for Outlook

support.microsoft.com

Sorry I forgot to mention, 587 TLS also gives the Invalid authentication (you can only send From) error. I requested the server to send the config again just to be sure:

Also is your sending address in XF configured to be the same as the actual email address you are logging in with? Sometimes those free providers don't allow you to "send" mail as another user through them (say something like no_reply@yourdomain.com and your Hotmail/Live/Outlook login is somethingelse@outlook.com).

It's the exact same email and I use a paid service.

 

[Paul B]

Didn't Outlook make a change recently related to "insecure apps", as Google did some time ago?

 

[Kay0501]

Didn't Outlook make a change recently related to "insecure apps", as Google did some time ago?

Hi, I don't really follow tech news so could you point me to the changes I should read regarding my Xenforo email problem?

 

[TPerry]

Hi, I don't really follow tech news so could you point me to the changes I should read regarding my Xenforo email problem?

If you are using Office-365 or Microsoft 365, this page tells you how to set it up.
If you are using either product (branded with your domain) then you definitely have the wrong SMTP server configured according to it.

How to set up a multifunction device or application to send emails using Microsoft 365 or Office 365

Learn how to set up printers, scanners, LOB applications to send emails using Microsoft 365 or Office 365.

learn.microsoft.com

Now, if you are using a different SMTP service... you really need to clarify that, as there may be some confusion as you mentioned Outlook and most assume referring to MS's email service and not the program.

The error you relate is a typical SMTP 550 generic error. The REAL teller is the you can only send FROM portion. It strongly indicates that the email address you are using to send from is NOT listed as a valid sender via SMTP. I'll ask once more, do you have your sending email that you are using in XF set up as either an email account OR an alias in your SMTP hosting site configuration that is allowed to send?



Many SMTP services will NOT allow you to send to using a different email address than what you log in with unless you have it listed as an alias for the log-in account. It is an anti-spam feature.

 

[Kay0501]

If you are using Office-365 or Microsoft 365, this page tells you how to set it up.
If you are using either product (branded with your domain) then you definitely have the wrong SMTP server configured according to it.

How to set up a multifunction device or application to send emails using Microsoft 365 or Office 365

Learn how to set up printers, scanners, LOB applications to send emails using Microsoft 365 or Office 365.

learn.microsoft.com

Now, if you are using a different SMTP service... you really need to clarify that, as there may be some confusion as you mentioned Outlook and most assume referring to MS's email service and not the program.

The error you relate is a typical SMTP 550 generic error. The REAL teller is the you can only send FROM portion. It strongly indicates that the email address you are using to send from is NOT listed as a valid sender via SMTP. I'll ask once more, do you have your sending email that you are using in XF set up as either an email account OR an alias in your SMTP hosting site configuration that is allowed to send?

View attachment 276541

Many SMTP services will NOT allow you to send to using a different email address than what you log in with unless you have it listed as an alias for the log-in account. It is an anti-spam feature.

Thank you for pointing out, it seemed I've caused some unnecessary confusion over my email provider. I do not use Office/Microsoft email, mine is from a local hosting provider.

We only ever created and have been using only 1 email since the start.

Spoiler: There's only 1 email

 

[TPerry]

Then it is an issue you will need to address with your MTA hosting provider, as they are apparently rejecting the "From" address as a valid sender.

 

[Kay0501]

Then it is an issue you will need to address with your MTA hosting provider, as they are apparently rejecting the "From" address as a valid sender.

I see, thank you. Could you explain what MTA is?

 

[TPerry]

I see, thank you. Could you explain what MTA is?

Mail Transfer Agent. It's what transfers the mail between different locations and can consist of Postfix, Sendmail or a few other programs. So it basically refers back to whomever hosts your mail service.