# Fresh Discourse/Docker install wont send mails **URL:** \ **Category:** Self-hosting\ **Created:** [November 10, 2022, 10:31pm UTC](https://meta.discourse.org/t/fresh-discourse-docker-install-wont-send-mails/245255 "2022-11-10T22:31:00Z")\ **Posts on this page:** 1\ **Showing post:** 1
**Author:** ![funktionierbar](https://sea3.discourse-cdn.com/meta/user_avatar/meta.discourse.org/funktionierbar/32/281388_2.png) [@funktionierbar](https://meta.discourse.org/u/funktionierbar)\ **Post date:** [November 10, 2022, 10:31pm UTC](https://meta.discourse.org/t/fresh-discourse-docker-install-wont-send-mails/245255/1 "2022-11-10T22:31:00Z")
Hi people, I want to switch a long standing forum from phpBB3 to Discourse. I managed to setup the Docker, and am able to access the Initial Setup. Unfortunately there is no mail being sent, so i can’t finish the init. I did some debugging and cant find the reason, so I am turning to you for help. My setup is like this, I have setup apache2 as a reverseproxy to the docker, which works. My mailserver is a mailcow docker on the same machine. The mailserver is tested thoroughly and works fine on a daily basis through SMTP with STARTTLS on Port 587 and webmail. the config in my app.yml looks like this: ```plaintext DISCOURSE_SMTP_ADDRESS: mail.example.com DISCOURSE_SMTP_PORT: 587 DISCOURSE_SMTP_USER_NAME: discourse@example.com DISCOURSE_SMTP_PASSWORD: "password" #DISCOURSE_SMTP_ENABLE_START_TLS: true # (optional, default true) #DISCOURSE_SMTP_DOMAIN: mail.example.com DISCOURSE_NOTIFICATION_EMAIL: discourse@example.com ``` when i run ./discourse-doctor i get: ```plaintext ==================== 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) [admin@example.com]: Sending mail to admin@example.com. . . Testing sending to admin@example.com using mail.example.com:587, username:discourse@example.com with plain auth. ======================================= ERROR ======================================== UNEXPECTED ERROR Cannot assign requested address - connect(2) for [correct ipv6]:587 ====================================== SOLUTION ======================================= This is not a common error. No recommended solution exists! Please report the exact error message above to https://meta.discourse.org/ (And a solution, if you find one!) ``` Being unable to find people with similar error messages on the web, I turned [to this thread](https://meta.discourse.org/t/troubleshoot-email-on-a-new-discourse-install/16326) I was easily able to connect to the mailserver with telnet from outside the container. What I tried inside the container: > getent hosts [mail.example.com](http://mail.example.com) provided the correct IPv6 Adress But then the errors started turning up: ```plaintext openssl s_client -connect mail.example.com:587 -starttls smtp 140124593714496:error:0200206E:system library:connect:Connection timed out:../crypto/bio/b_sock2.c:110: 140124593714496:error:2008A067:BIO routines:BIO_connect:connect error:../crypto/bio/b_sock2.c:111: connect:errno=110 ``` ```plaintext openssl s_client -6 -connect "[correct IPv6]:587" -starttls smtp 139918557709632:error:02002063:system library:connect:Cannot assign requested address:../crypto/bio/b_sock2.c:110: 139918557709632:error:2008A067:BIO routines:BIO_connect:connect error:../crypto/bio/b_sock2.c:111: connect:errno=99 ``` ```plaintext openssl s_client -connect smtp.gmail.com:587 -starttls smtp ``` works just fine When I try the ` openssl s_client -connect mail.example.com:587 -starttls smtp` from outside the container, It works also fine. My mailcow/postfix logs show nothing… I am stumped. Can you help me where to look next? --- _[View the full topic](https://meta.discourse.org/t/fresh-discourse-docker-install-wont-send-mails/245255)._