# Issues with mail sending to SMTP relay

**URL:** <https://meta.discourse.org/t/issues-with-mail-sending-to-smtp-relay/259016>\
**Category:** Self-hosting\
**Tags:** email\
**Created:** [March 22, 2023, 10:18am UTC](https://meta.discourse.org/t/issues-with-mail-sending-to-smtp-relay/259016 "2023-03-22T10:18:31Z")\
**Posts on this page:** 1\
**Showing post:** 1

<div class="post-metadata">

**Author:** ![altmvogi](https://avatars.discourse-cdn.com/v4/letter/a/bbce88/32.png) [@altmvogi](https://meta.discourse.org/u/altmvogi)\
**Post date:** [March 22, 2023, 10:18am UTC](https://meta.discourse.org/t/issues-with-mail-sending-to-smtp-relay/259016/1 "2023-03-22T10:18:32Z")

</div>

Hi,  
we are having problems with sending emails via an SMTP relay with no user and password required. i am able to send emails to the relay using mailx / sendmail.  
those are the settings.

```plaintext
 DISCOURSE_SMTP_ADDRESS: xyz.example.com (obfuscated)
 DISCOURSE_SMTP_PORT: 587
 DISCOURSE_SMTP_AUTHENTICATION: plain

```

what I get back, when using the discourse\_doctor is giving this error.

```plaintext
Net::ReadTimeout

```

it appears to me like the SMPT message sent is mal-crafted as we send stuff, but we do not get anything back on port 587. this is provable with a Wireshark trace.

can you please elaborate how to put more verbose logging or additional debugging so we can further analyze the problem? the regular logs don’t tell me anything. i found backtrace, but I am not a ruby developer so cannot interpret this.

```plaintext
/usr/local/lib/ruby/3.2.0/net/protocol.rb:229:in `rbuf_fill'

/usr/local/lib/ruby/3.2.0/net/protocol.rb:199:in `readuntil'

/usr/local/lib/ruby/3.2.0/net/protocol.rb:209:in `readline'

net-smtp-0.3.3/lib/net/smtp.rb:1057:in `recv_response'

net-smtp-0.3.3/lib/net/smtp.rb:659:in `block in do_start'

net-smtp-0.3.3/lib/net/smtp.rb:1067:in `critical'

net-smtp-0.3.3/lib/net/smtp.rb:659:in `do_start'

net-smtp-0.3.3/lib/net/smtp.rb:611:in `start'

/var/www/discourse/vendor/bundle/ruby/3.2.0/bundler/gems/mail-5b700fc95ee6/lib/mail/network/delivery_methods/smtp.rb:109:in `start_smtp_session'

/var/www/discourse/vendor/bundle/ruby/3.2.0/bundler/gems/mail-5b700fc95ee6/lib/mail/network/delivery_methods/smtp.rb:100:in `deliver!'

/var/www/discourse/vendor/bundle/ruby/3.2.0/bundler/gems/mail-5b700fc95ee6/lib/mail/message.rb:269:in `deliver!'

/usr/local/lib/ruby/3.2.0/delegate.rb:87:in `method_missing'

/var/www/discourse/lib/email/sender.rb:286:in `send'

/var/www/discourse/app/jobs/regular/user_email.rb:79:in `send_user_email'

/var/www/discourse/app/jobs/regular/user_email.rb:39:in `execute'

/var/www/discourse/plugins/chat/lib/chat/user_email_extension.rb:6:in `execute'

/var/www/discourse/app/jobs/base.rb:249:in `block (2 levels) in perform'

rails_multisite-4.0.1/lib/rails_multisite/connection_management.rb:80:in `with_connection'

/var/www/discourse/app/jobs/base.rb:236:in `block in perform'

/var/www/discourse/app/jobs/base.rb:232:in `each'

/var/www/discourse/app/jobs/base.rb:232:in `perform'

sidekiq-6.5.8/lib/sidekiq/processor.rb:202:in `execute_job'

sidekiq-6.5.8/lib/sidekiq/processor.rb:170:in `block (2 levels) in process'

sidekiq-6.5.8/lib/sidekiq/middleware/chain.rb:177:in `block in invoke'

/var/www/discourse/lib/sidekiq/pausable.rb:134:in `call'

sidekiq-6.5.8/lib/sidekiq/middleware/chain.rb:179:in `block in invoke'

sidekiq-6.5.8/lib/sidekiq/middleware/chain.rb:182:in `invoke'

sidekiq-6.5.8/lib/sidekiq/processor.rb:169:in `block in process'

sidekiq-6.5.8/lib/sidekiq/processor.rb:136:in `block (6 levels) in dispatch'

sidekiq-6.5.8/lib/sidekiq/job_retry.rb:113:in `local'

sidekiq-6.5.8/lib/sidekiq/processor.rb:135:in `block (5 levels) in dispatch'

sidekiq-6.5.8/lib/sidekiq.rb:44:in `block in <module:Sidekiq>'

sidekiq-6.5.8/lib/sidekiq/processor.rb:131:in `block (4 levels) in dispatch'

sidekiq-6.5.8/lib/sidekiq/processor.rb:263:in `stats'

sidekiq-6.5.8/lib/sidekiq/processor.rb:126:in `block (3 levels) in dispatch'

sidekiq-6.5.8/lib/sidekiq/job_logger.rb:13:in `call'

sidekiq-6.5.8/lib/sidekiq/processor.rb:125:in `block (2 levels) in dispatch'

sidekiq-6.5.8/lib/sidekiq/job_retry.rb:80:in `global'

sidekiq-6.5.8/lib/sidekiq/processor.rb:124:in `block in dispatch'

sidekiq-6.5.8/lib/sidekiq/job_logger.rb:39:in `prepare'

sidekiq-6.5.8/lib/sidekiq/processor.rb:123:in `dispatch'

sidekiq-6.5.8/lib/sidekiq/processor.rb:168:in `process'

sidekiq-6.5.8/lib/sidekiq/processor.rb:78:in `process_one'

sidekiq-6.5.8/lib/sidekiq/processor.rb:68:in `run'

sidekiq-6.5.8/lib/sidekiq/component.rb:8:in `watchdog'

sidekiq-6.5.8/lib/sidekiq/component.rb:17:in `block in safe_thread'

```

I downgraded the application to the latest stable release, which did not solve this problem. the guy working on this before is on PTO, so I cannot tell to which version this was before the latest update happened. I also realized, there were recent code changes in the mail area. maybe problems there ?

thank you

---

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