500 5.5.1 Invalid command: Cannot send mail with Discourse on new install but can from command line (on digital ocean)

Installation
1

I’m getting the following error using ./discourse-docker on Digital Ocean after installation

==================== MAIL TEST ====================
For a robust test, get an address from http://www.mail-tester.com/
Or just send a test message to yourself.
Email address for mail test? ('n' to skip) [forum@jamaicans.dev]: 
Sending mail to forum@jamaicans.dev. . . 
Testing sending to forum@jamaicans.dev using mail.jamaicans.dev:587.
======================================== ERROR ========================================
                                    UNEXPECTED ERROR

500 5.5.1 Invalid command
1 Like
2

is forum@jamaicans.dev a valid email Address?
Are you using a custom SMTP?

3

Yes, I’m running my own Mail server using Mailu -> Mailu — Mailu, Docker based mail server.

I wrote a python script to test if it is send emails using the SMTP credentials, and I’m able to send and receive emails. I also tried Telnet, which works. The port is running on 587 with StartTLS. DMARC and SPF has already been setup.

The mail account has a % sign in the password. I noticed in the app.yaml that the passowrd shouldn’t have in a #. Do you think this would be the culprit?

4

Enclose the password in Quotes e.g. 'P@$$w0RD%100' that should make it work

5

It is already enclosed

6

Why not change the password and find out?

7

I did, waiting on the rebuild to complete… but just in case it fails, I wanted to find out if anyone else got this message

8

It didn’t work. I’ll probably just use mail gun

9

Can you share your Python script? I, too, installed mailu, and I like to test it.

Update: Nevermind, I created it myself via Sending Emails With Python – Real Python. Mailu works (without TLS, as I haven’t figured out how to use letsencrypt with both mailu and caddy), but discourse doesn’t send emails …

2 Likes
10

Hi,
It also worked for me. I made some changes to mail settings and it started to work. Sorry for not indicating that I got it to work.

2 Likes
11

I got it working, too. Testing it with discourse-doctor helped a lot.

2 Likes
12

I have the same error. Do either of you remember what you did to fix it?

13

Honestly, no, but try to get it working with example seen in real python first. I think this led me to the solution.

1 Like