[Help]: Cannot Send Email - TLS Issue #368

socal0001 · 2023-11-03T21:02:34Z

socal0001
Nov 3, 2023

Controller Version

v5.12.7

Describe Your Issue or Question

I am unable to send email using v5.12 but had the same problem with v5.9. It used to work many version ago, just too busy to figure it out.

Expected Behavior

Be able to send email

Steps to Reproduce

Go to server settings, mail setting
Put in legit local mail server (not I host a relay server, Postfix, on the LAN).
Try to send a test email and fails.

How You're Launching the Container

Portainer:
version: "3.1"

services:
  omada-controller:
    container_name: omada-controller
    image: mbentley/omada-controller:latest
    restart: unless-stopped
    ulimits:
      nofile:
        soft: 4096
        hard: 8192
    stop_grace_period: 60s
    network_mode: host
    environment:
      - PUID=508
      - PGID=508
      - MANAGE_HTTP_PORT=8088
      - MANAGE_HTTPS_PORT=8043
      - PORTAL_HTTP_PORT=8088
      - PORTAL_HTTPS_PORT=8843
      - PORT_APP_DISCOVERY=27001
      - PORT_ADOPT_V1=29812
      - PORT_UPGRADE_V1=29813
      - PORT_MANAGER_V1=29811
      - PORT_MANAGER_V2=29814
      - PORT_DISCOVERY=29810
      - SHOW_SERVER_LOGS=true
      - SHOW_MONGODB_LOGS=false
      - SSL_CERT_NAME=tls.crt
      - SSL_KEY_NAME=tls.key
      - TZ=America/Los_Angeles
    volumes:
      - omada-data:/opt/tplink/EAPController/data
      - omada-logs:/opt/tplink/EAPController/logs
      - /etc/timezone:/etc/timezone:ro
      - /etc/localtime:/etc/localtime:ro
volumes:
  omada-data:
  omada-logs:

Container Logs

DEBUG: setDebug: JavaMail version 1.6.2
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle]
DEBUG SMTP: useEhlo true, useAuth false
DEBUG SMTP: trying to connect to host "127.0.0.1", port 25, isSSL false
220 docker01.home.REDACTED.com ESMTP Postfix (Debian/GNU)
DEBUG SMTP: connected to host "127.0.0.1", port: 25
EHLO docker01.home.REDACTED.com
250-docker01.home.REDACTED.com
250-PIPELINING
250-SIZE 10240000
250-VRFY
250-ETRN
250-STARTTLS
250-ENHANCEDSTATUSCODES
250-8BITMIME
250-DSN
250-SMTPUTF8
250 CHUNKING
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "SIZE", arg "10240000"
DEBUG SMTP: Found extension "VRFY", arg ""
DEBUG SMTP: Found extension "ETRN", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "DSN", arg ""
DEBUG SMTP: Found extension "SMTPUTF8", arg ""
DEBUG SMTP: Found extension "CHUNKING", arg ""
STARTTLS
220 2.0.0 Ready to start TLS
11-03-2023 13:53:15.904 WARN [email-task-1] [] c.t.s.o.c.s.a(): Send mail exception Could not convert socket to TLS
DEBUG: setDebug: JavaMail version 1.6.2
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle]
DEBUG SMTP: useEhlo true, useAuth false
DEBUG SMTP: trying to connect to host "127.0.0.1", port 25, isSSL false
220 docker01.home.REDACTED.com ESMTP Postfix (Debian/GNU)
DEBUG SMTP: connected to host "127.0.0.1", port: 25
EHLO docker01.home.REDACTED.com
250-docker01.home.REDACTED.com
250-PIPELINING
250-SIZE 10240000
250-VRFY
250-ETRN
250-STARTTLS
250-ENHANCEDSTATUSCODES
250-8BITMIME
250-DSN
250-SMTPUTF8
250 CHUNKING
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "SIZE", arg "10240000"
DEBUG SMTP: Found extension "VRFY", arg ""
DEBUG SMTP: Found extension "ETRN", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "DSN", arg ""
DEBUG SMTP: Found extension "SMTPUTF8", arg ""
DEBUG SMTP: Found extension "CHUNKING", arg ""
STARTTLS
220 2.0.0 Ready to start TLS
11-03-2023 13:54:38.692 WARN [email-task-2] [] c.t.s.o.c.s.a(): Send mail exception Could not convert socket to TLS

MongoDB Logs

Mongo does not seem relevant, but these are the logs from Postfix

2023-11-03T12:03:53.605291-07:00 docker01 postfix/cleanup[313673]: 8FD4C80648: message-id=<20231103190353.8FD4C80648@docker01.home.REDACTED.com>
2023-11-03T12:03:53.607969-07:00 docker01 postfix/qmgr[300698]: 8FD4C80648: from=<root@docker01.home.REDACTED.com>, size=814, nrcpt=1 (queue active)
2023-11-03T12:03:53.722502-07:00 docker01 postfix/smtp[313675]: 8FD4C80648: to=<REDACTED@REDACTED.com>, relay=192.168.redacted.50[192.168.redacted.50]:25, delay=0.16, delays=0.04/0.03/0.06/0.02, dsn=2.0.0, status=sent (250 2.0.0 Ok: queued as AF4277FD66)
2023-11-03T12:03:53.722763-07:00 docker01 postfix/qmgr[300698]: 8FD4C80648: removed
2023-11-03T13:53:15.888576-07:00 docker01 postfix/smtpd[318837]: connect from localhost[127.0.0.1]
2023-11-03T13:53:15.904592-07:00 docker01 postfix/smtpd[318837]: SSL_accept error from localhost[127.0.0.1]: -1
2023-11-03T13:53:15.904928-07:00 docker01 postfix/smtpd[318837]: warning: TLS library problem: error:0A000416:SSL routines::sslv3 alert certificate unknown:../ssl/record/rec_layer_s3.c:1586:SSL alert number 46:
2023-11-03T13:53:15.905062-07:00 docker01 postfix/smtpd[318837]: lost connection after STARTTLS from localhost[127.0.0.1]
2023-11-03T13:53:15.905156-07:00 docker01 postfix/smtpd[318837]: disconnect from localhost[127.0.0.1] ehlo=1 starttls=0/1 commands=1/2
2023-11-03T13:54:38.678564-07:00 docker01 postfix/smtpd[318837]: connect from localhost[127.0.0.1]
2023-11-03T13:54:38.692330-07:00 docker01 postfix/smtpd[318837]: SSL_accept error from localhost[127.0.0.1]: -1
2023-11-03T13:54:38.692576-07:00 docker01 postfix/smtpd[318837]: warning: TLS library problem: error:0A000416:SSL routines::sslv3 alert certificate unknown:../ssl/record/rec_layer_s3.c:1586:SSL alert number 46:
2023-11-03T13:54:38.692708-07:00 docker01 postfix/smtpd[318837]: lost connection after STARTTLS from localhost[127.0.0.1]
2023-11-03T13:54:38.692802-07:00 docker01 postfix/smtpd[318837]: disconnect from localhost[127.0.0.1] ehlo=1 starttls=0/1 commands=1/2

Additional Context

No problems relaying from other apps.

Can we disable the requirment for TLS/SSL? I would guess that would fix it. My guess is the controller wants signed and validated certificates and my little postfix relay is not providing those and I don't want to go to the trouble of creating them for this private and firewalled setup.

Thanks in advance,
JT

Answered by mbentley

Nov 4, 2023

I just tested and if I set smtpd_use_tls = no while smtpd_tls_cert_file and smtpd_tls_key_file are commented out, I can send mail successfully using my Omada mail settings that I posted above.

View full answer

socal0001 · 2023-11-03T21:21:34Z

socal0001
Nov 3, 2023
Author

This did not work for me:
https://community.tp-link.com/en/business/forum/topic/267954

0 replies

mbentley · 2023-11-03T23:31:05Z

mbentley
Nov 3, 2023
Maintainer

I use a local postfix server to relay my mail as well. Here are my settings:

mailhub.casa.mbentley.net is just a DNS alias to my host running postfix. If similar settings do not work for you, it's likely a postfix setting.

Here is most of my postfix config where I am relaying mail:

smtpd_banner = $myhostname ESMTP $mail_name (Debian/GNU)
biff = no

# appending .domain is the MUA's job.
append_dot_mydomain = no
readme_directory = no

# TLS parameters
smtpd_tls_cert_file = /cert/fullchain.cer
smtpd_tls_key_file = /cert/key.key
smtpd_use_tls = yes
smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

myhostname = mailhost.example.com
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
myorigin = /etc/mailname
mydestination = mailhost.example.com, localhost.example.com, localhost
relayhost = smtp.example.com:587
mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128 192.168.0.0/24
mailbox_command = procmail -a "$EXTENSION"
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = all
inet_protocols = ipv4
soft_bounce = yes
compatibility_level = 2

smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/sasl/passwd
smtp_sasl_security_options = noanonymous
smtp_sasl_tls_security_options = noanonymous
smtp_sasl_mechanism_filter = AUTH LOGIN

smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated defer_unauth_destination
smtp_generic_maps = hash:/etc/postfix/generic
defer_transports =

0 replies

socal0001 · 2023-11-04T14:32:51Z

socal0001
Nov 4, 2023
Author

Thanks, I'm guessing it is these in my setting.
smtpd_tls_cert_file=/etc/ssl/certs/ssl-cert-snakeoil.pem
smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key

Where did you get your fullchain.cer and key.key? I'd very much prefer not to try to set up a let's encrypt solution. Are yours default or custom self signed? Mine are default.

I've been running these postfix relays for over a decade and never had any app (and I self host many) have any issue, weird.

Omada used to work. Can we disable to the attempt at SSL/TLS in some Omada setting?

2 replies

mbentley Nov 4, 2023
Maintainer

Mine are certs from an acme based issuer (in this case, ZeroSSL, which is similar to Let’s Encrypt). I’ll see if resetting mine to the default certs causes an issue with the mail test.

mbentley Nov 4, 2023
Maintainer

I just tested and if I set smtpd_use_tls = no while smtpd_tls_cert_file and smtpd_tls_key_file are commented out, I can send mail successfully using my Omada mail settings that I posted above.

Answer selected by mbentley

socal0001 · 2023-11-04T17:31:59Z

socal0001
Nov 4, 2023
Author

You are so kind to create this docker container and provide support tirelessly, thank you.

Commenting out the certs solved.

Thanks again!!

0 replies

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[Help]: Cannot Send Email - TLS Issue #368

socal0001 Nov 3, 2023

Controller Version

Describe Your Issue or Question

Expected Behavior

Steps to Reproduce

How You're Launching the Container

Container Logs

MongoDB Logs

Additional Context

Replies: 4 comments · 2 replies

socal0001 Nov 3, 2023 Author

mbentley Nov 3, 2023 Maintainer

socal0001 Nov 4, 2023 Author

mbentley Nov 4, 2023 Maintainer

mbentley Nov 4, 2023 Maintainer

socal0001 Nov 4, 2023 Author

socal0001
Nov 3, 2023

Replies: 4 comments 2 replies

socal0001
Nov 3, 2023
Author

mbentley
Nov 3, 2023
Maintainer

socal0001
Nov 4, 2023
Author

mbentley Nov 4, 2023
Maintainer

mbentley Nov 4, 2023
Maintainer

socal0001
Nov 4, 2023
Author