Sending emails not working

[Kristian]

My digitalocean discourse droplet can’t send mails. The error I get is:

Delivered mail d8f9bf03-a3ce-4b42-8226-fc4f40a9c724@foo.barbar.com (5099.4ms)

Job exception: 504 5.7.4 Unrecognized authentication type [BL0PR0102CA0036.prod.exchangelabs.com]

My settings are:

  DISCOURSE_SMTP_ADDRESS: smtp.office365.com
  DISCOURSE_SMTP_PORT: 587
  DISCOURSE_SMTP_USER_NAME: foo@bar.com
  DISCOURSE_SMTP_PASSWORD: "mypassword"
  DISCOURSE_SMTP_ENABLE_START_TLS: true           # (optional, default true)

I have tried telnet from the droplet and it gives no errors:
telnet smtp.office365.com 587

What could be the problem? I have tried the smtp settings combination locally from python and it works so I assume that’s not the problem.

[mik]

Hi,
Try to add:

  DISCOURSE_SMTP_AUTHENTICATION: login

And at end of app.yml:

 - exec: rails r "SiteSetting.notification_email='foo@bar.com'"`

[Kristian]

Hi mik
The exec statement fails:

FAILED

--------------------

Pups::ExecError: rails r "SiteSetting.notification_email='foo@bar.com'"` failed with return #<Process::Status: pid 2229 exit 2>

Location of failure: /pups/lib/pups/exec_command.rb:112:in `spawn'

exec failed with the params "rails r \"SiteSetting.notification_email='foo@bar.com'\"`"

9628e31c775b74ad0f3a555b6af27701aa40b1f8b86419fa44a7c389cc5e34ae

** FAILED TO BOOTSTRAP ** please scroll up and look for earlier error messages, there may be more than one.

./discourse-doctor may help diagnose the problem.

[Kristian]

Update leaving out the exec command but adding:

  DISCOURSE_SMTP_AUTHENTICATION: login

does not produce return an error I only get:
Delivered mail be6d8718-5445-48cc-a120-6d6d1eab9eb7@discourse.bar.com (4307.2ms)

But I still don’t get an email in my inbox (I checked the spam folder)

[mik]

You can try this in order to try to find the good configuration and perhaps have some error message:

docker exec -t -i  id_of_your_container /bin/bash

Then inside the container:

apt install s-nail
echo "This is the message body and contains the message" | s-nail -r "foo@bar.com" -s mysubject -S "smtp=smtp.office365.com:587" -S smtp-use-starttls -S smtp-auth=login -S smtp-auth-user="foo@bar.com" -S smtp-auth-password="xxxxxxxx" -S ssl-verify=ignore youremail@example.com

You can change the different value (ie : smtp-auth=login ) to try to find the good one. And perhaps you will have more precise error message.

[Kristian]

echo "This is the message body and contains the message" | s-nail -r "foo@bar.com" -s mysubject -S "smtp=smtp.office365.com:587" -S smtp-use-starttls -S smtp-auth=login -S smtp-auth-user="foo@bar.com" -S smtp-auth-password="xxxxxxxx" -S ssl-verify=ignore youremail@example.com

This worked and I got the mail! I had to change the smtp-auth-password=“xxxxxxxx” to single quotes though since my password starts with an ‘!’.

The only difference I can see to my config is this flag:
-S ssl-verify=ignore

Do I have to add that too?
Thanks for your help!

[mik]

Try to add:

DISCOURSE_SMTP_OPENSSL_VERIFY_MODE: none

In your config, it is the same as ssl-verify=ignore .

[Kristian]

No errors but still no email in the inbox To recap, this is my config now:

  DISCOURSE_SMTP_ADDRESS: smtp.office365.com
  DISCOURSE_SMTP_PORT: 587
  DISCOURSE_SMTP_USER_NAME: info@foo.com
  DISCOURSE_SMTP_PASSWORD: 'xxx'
  DISCOURSE_SMTP_ENABLE_START_TLS: true           # (optional, default true)
  DISCOURSE_SMTP_AUTHENTICATION: login
  DISCOURSE_SMTP_OPENSSL_VERIFY_MODE: none

[mik]

Please try to add this again (it is the same as “-r” option in the s-nail command line test :

  - exec: rails r "SiteSetting.notification_email='foo@bar.com'"`

The email must be the same as your account.

And check the indentation in the file app.yml, and do not forget the “-” at the beginning. There is 2 space then the “-” then a space then “exec…”

[Capstan (William Carter)]

I’m having this problem also. I spun up a droplet with Discourse on Digital Ocean as well. I used the “sudo ./discourse-doctor” command after trying all of these suggestions and rebuilding each time ( sudo ./launcher rebuild app).

504 5.7.4 Unrecognized authentication type [BL0PR01CA0015.prod.exchangelabs.com]

s-nail from within the container did work for me also, no problem. And I tried it without the “-S ssl-verify=ignore” clause, worked fine. Can someone verify that what gets installed on the digital ocean droplet does send email correctly?

[riking (Kane York)]

Find out from your mail admins what the valid values of smtp_authentication are, and set DISCOURSE_SMTP_AUTHENTICATION to one that works.

[Kristian]

Thanks for all the help, I have given up and switched to another forum solution.

[Capstan (William Carter)]

It is Microsoft, their instructions are as follows, no smtp_authentication is specified;

• SMTP server name smtp.office365.com
• SMTP port 587
• SMTP encryption method STARTTLS

Do you not support this kind of server? Can you simply make an account, connect to it, and tell us what the settings should be?

[m.jason.miller (Jason)]

DISCOURSE_SMTP_OPENSSL_VERIFY_MODE: none

This solved my issue thanks!