### Author:  [@philion](https://meta.discourse.org/u/philion)
#### Post date: [March 9, 2025, 5:32am UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/1 "2025-03-09T05:32:07Z")
I am trying to troubleshoot SMTP problems using `./discourse-doctor`
The closest related issue I could find is [Yet other SMTP 587 port email various errors](https://meta.discourse.org/t/yet-other-smtp-587-port-email-various-errors/264267).
Before implementing the suggestions, I got consistent timeout.
After configuring:
```plaintext
DISCOURSE_SMTP_FORCE_TLS: true
DISCOURSE_SMTP_ENABLE_START_TLS: false
```
I get the following from `discourse-doctor`:
```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@burlyqna.org]:
Sending mail to admin@burlyqna.org. . .
Testing sending to admin@burlyqna.org using smtp.mailfence.com:465, username:philion@mailfence.com with plain auth.
SMTP server connection successful.
Sending to admin@burlyqna.org. . .
Sending mail failed.
end of file reached
```
See: [http://talk.burlyqna.org/NjdhMDAwYTk4NmM3MmM1.txt](http://talk.burlyqna.org/NjdhMDAwYTk4NmM3MmM1.txt)
I am able to externally validate the SMTP server config with:
```plaintext
swaks --to philion@gmail.com --from admin@burlyqna.org --server smtp.mailfence.com:465 --auth LOGIN --tlsc --auth-user philion@mailfence.com
```
Any clues how `SMTP server connection successful.` but `Sending mail failed.`?
Many thanks,
Paul
---
### Author:  [@thoka](https://meta.discourse.org/u/thoka)
#### Post date: [March 9, 2025, 6:42am UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/3 "2025-03-09T06:42:09Z")
For TLS you should use port 587?
I would try to add `puts error.backtrace` (or similar) after
>
and rerun `discourse-doctor`.
---
### Author:  [@sam](https://meta.discourse.org/u/sam)
#### Post date: [March 9, 2025, 9:19am UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/4 "2025-03-09T09:19:23Z")
> [@support-bot](#):
>
> **Suggested response:**
> The error message `"SMTP server connection successful. Sending mail failed. end of file reached"` in your `discourse-doctor` tests likely indicates an issue with how the Discourse environment interacts with your SMTP server during mail submission.
>
> 1. First, confirm your SMTP settings in `app.yml`:
>
> -
>
> ```plaintext
>
> ```
>
> DISCOURSE\_SMTP\_ADDRESS: [smtp.mailfence.com](http://smtp.mailfence.com)
> DISCOURSE\_SMTP\_PORT: 465
> DISCOURSE\_SMTP\_USER\_NAME: [philion@mailfence.com](mailto:philion@mailfence.com)
> DISCOURSE\_SMTP\_PASSWORD: [your password]
> DISCOURSE\_SMTP\_FORCE\_TLS: true
> DISCOURSE\_SMTP\_ENABLE\_START\_TLS: false
> DISCOURSE\_SMTP\_DOMAIN: [your domain] # Ensure this matches your domain!
>
> ````plaintext
>
> Adding the `DISCOURSE_SMTP_DOMAIN` setting is essential in your case. Many SMTP servers, such as Google’s smtp-relay, reject connections with `EHLO localhost`. This setting ensures that the HELO/EHLO command uses your fully qualified domain name (FQDN).
> * After adding or modifying these settings, rebuild your app:
>
> 1. ```
> cd /var/discourse
> ./launcher rebuild app
>
> ````
>
> 1. Test your configuration by sending test emails from the admin panel. Note: While `discourse-doctor` may still fail in some specific configurations due to how it bypasses the regular app email pipeline, the admin panel tests are more reliable.
>
> Additionally, ensure your DNS records (such as SPF, DKIM, and DMARC) are correctly configured for your domain to avoid rejection from the SMTP server.
>
> **Helpful resources:**
>
> - [Discourse SMTP sends `EHLO localhost`](https://meta.discourse.org/t/discourse-smtp-sends-ehlo-localhost-instead-of-domain-breaking-google-smtp-relay/176755): Detailed explanation and solution using the `DISCOURSE_SMTP_DOMAIN` setting.
> - [Troubleshooting Email on a New Install](https://meta.discourse.org/t/troubleshooting-email-on-a-new-discourse-install/16326): A comprehensive guide to diagnosing and resolving email setup issues in Discourse.
> - [Setting up DISCOURSE\_SMTP\_DOMAIN](https://github.com/discourse/discourse_docker/blob/main/samples/standalone.yml): Sample app.yml configuration file with the relevant settings.
>
> **Additional context:**
> The “end of file reached” message is common when the SMTP handshake fails or abruptly terminates. With correct domain settings (`DISCOURSE_SMTP_DOMAIN`) and rebuilding, these issues should be resolved for most configurations. However, always consult your email provider’s documentation for server-specific nuances.
This is what our auto responder came up with, I think trying smtp domain is probably worth a shot.
---
### Author:  [@philion](https://meta.discourse.org/u/philion)
#### Post date: [March 9, 2025, 3:48pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/5 "2025-03-09T15:48:26Z")
Thomas,
There is a lot of discussion about 465 in the support forums. Based on my reading, it looks like Discourse makes a lot of assumptions about SSL and TLS over SMTP, and there are a handful of env vars that control the detailed behaviors.
HOWEVER, given the number of reported errors and related questions in these forums, I have the strong impression that these settings are poorly documented and difficult to use. And seeing similar problems going back to 2017, this has been an issue for years now.
Searches for “port 465” or “Net::ReadTimeout smtp” can reveal a long list of similar issues.
---
### Author:  [@philion](https://meta.discourse.org/u/philion)
#### Post date: [March 9, 2025, 3:48pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/6 "2025-03-09T15:48:59Z")
I’ll give this a try. Thanks!
---
### Author:  [@philion](https://meta.discourse.org/u/philion)
#### Post date: [March 9, 2025, 4:18pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/7 "2025-03-09T16:18:39Z")
Thomas,
I’m trying to find this file on the docker build, and I can’t. I see that it’s wrapped in a container, but I’ve cloned `discourse/discourse_docker` not `discourse/discourse`.
When I try to enter the app with `launcher enter app`, there’s no way to edit that file or to install vi.
I cannot find any docs or flags for running `./discourse-doctor` with debug logs turned on.
Fails in the same way: Can’t send email, ./discourse-doctor reports the same error.
---
### Author:  [@philion](https://meta.discourse.org/u/philion)
#### Post date: [March 9, 2025, 4:19pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/8 "2025-03-09T16:19:27Z")
Updated app.yml as suggest, rebuilt app (no email), tried ./discourse-doctor and got the same error message.
---
### Author:  [@thoka](https://meta.discourse.org/u/thoka)
#### Post date: [March 9, 2025, 4:20pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/9 "2025-03-09T16:20:45Z")
```plaintext
./launcher enter app
sudo apt update && sudo apt install neovim -y
```
should help.
---
### Author:  [@philion](https://meta.discourse.org/u/philion)
#### Post date: [March 9, 2025, 4:31pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/10 "2025-03-09T16:31:32Z")
> [@thoka](#):
>
> ```plaintext
> sudo apt update && sudo apt install neovim -y
>
> ```
Thanks! I’m getting pretty long-in-the-tooth when I can’t “sudo apt install vi”. I have to remember it’s called `neovim` now.
---
### Author:  [@philion](https://meta.discourse.org/u/philion)
#### Post date: [March 9, 2025, 4:39pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/11 "2025-03-09T16:39:49Z")
Given the suggested change to dump stack trace, I offer:[http://talk.burlyqna.org/ODgyZjg5Y2QyMTU1ZmEx.txt](http://talk.burlyqna.org/ODgyZjg5Y2QyMTU1ZmEx.txt)
The relevant snippet:
```plaintext
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-protocol-0.2.2/lib/net/protocol.rb:237:in `rbuf_fill'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-protocol-0.2.2/lib/net/protocol.rb:199:in `readuntil'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-protocol-0.2.2/lib/net/protocol.rb:209:in `readline'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:1017:in `recv_response'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:1008:in `block in getok'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:1027:in `critical'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:1006:in `getok'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:986:in `quit'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:732:in `do_finish'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:645:in `ensure in start'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:645:in `start'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/mail-2.8.1/lib/mail/network/delivery_methods/smtp.rb:109:in `start_smtp_session'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/mail-2.8.1/lib/mail/network/delivery_methods/smtp.rb:100:in `deliver!'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/mail-2.8.1/lib/mail/message.rb:269:in `deliver!'
/usr/local/lib/ruby/3.3.0/delegate.rb:87:in `method_missing'
/var/www/discourse/lib/email/sender.rb:296:in `send'
```
---
### Author:  [@thoka](https://meta.discourse.org/u/thoka)
#### Post date: [March 9, 2025, 4:53pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/12 "2025-03-09T16:53:14Z")
Seems like the other side terminated the connection.
btw: [http://talk.burlyqna.org/NjdhMDAwYTk4NmM3MmM1.txt](http://talk.burlyqna.org/NjdhMDAwYTk4NmM3MmM1.txt) is not available any more
---
### Author:  [@philion](https://meta.discourse.org/u/philion)
#### Post date: [March 9, 2025, 4:58pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/13 "2025-03-09T16:58:10Z")
Do those log files get retained when I rebuild?
---
### Author:  [@philion](https://meta.discourse.org/u/philion)
#### Post date: [March 9, 2025, 6:51pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/14 "2025-03-09T18:51:51Z")
I updated passwords to remove symbols, waited for the SMTP auth propagation delay (long enough to make lunch), confirmed proper creds to correctly send email with `swaks`, and…
Same error.
I notice rebuilding removes the stacktrace dump, so I’m going to add that back and try `./launcher destroy app && ./launcher start app`
---
### Author:  [@philion](https://meta.discourse.org/u/philion)
#### Post date: [March 9, 2025, 6:59pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/15 "2025-03-09T18:59:28Z")
Installed debug trace, ran doctor:
[http://talk.burlyqna.org/NWQ5MjBlMTIwN2JiNGNl.txt](http://talk.burlyqna.org/NWQ5MjBlMTIwN2JiNGNl.txt)
```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@burlyqna.org]:
Sending mail to admin@burlyqna.org. . .
Testing sending to admin@burlyqna.org using smtp.mailfence.com:465, username:philion with plain auth.
SMTP server connection successful.
Sending to admin@burlyqna.org. . .
Sending mail failed.
end of file reached
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-protocol-0.2.2/lib/net/protocol.rb:237:in `rbuf_fill'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-protocol-0.2.2/lib/net/protocol.rb:199:in `readuntil'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-protocol-0.2.2/lib/net/protocol.rb:209:in `readline'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:1017:in `recv_response'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:1008:in `block in getok'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:1027:in `critical'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:1006:in `getok'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:986:in `quit'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:732:in `do_finish'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:645:in `ensure in start'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/net-smtp-0.5.1/lib/net/smtp.rb:645:in `start'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/mail-2.8.1/lib/mail/network/delivery_methods/smtp.rb:109:in `start_smtp_session'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/mail-2.8.1/lib/mail/network/delivery_methods/smtp.rb:100:in `deliver!'
/var/www/discourse/vendor/bundle/ruby/3.3.0/gems/mail-2.8.1/lib/mail/message.rb:269:in `deliver!'
```
---
### Author:  [@thoka](https://meta.discourse.org/u/thoka)
#### Post date: [March 9, 2025, 7:02pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/16 "2025-03-09T19:02:18Z")
Did you try using your full email as login name?
---
### Author:  [@philion](https://meta.discourse.org/u/philion)
#### Post date: [March 9, 2025, 7:11pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/17 "2025-03-09T19:11:28Z")
Updated `app.yml` to use full email as user, redeployed with `./launcher destroy app && ./launcher start app`.
Same error: [http://talk.burlyqna.org/ZDg1YWE1YTA2YWU1Zjhj.txt](http://talk.burlyqna.org/ZDg1YWE1YTA2YWU1Zjhj.txt)
Destroy and start also wiped out the debug, but I’m going to assume the same issue:
```plaintext
case rv = @io.read_nonblock(BUFSIZE, tmp, exception: false)
```
returns a nil, and that results in a EOF and non/error response.
>
---
### Author:  [@philion](https://meta.discourse.org/u/philion)
#### Post date: [March 10, 2025, 6:24pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/18 "2025-03-10T18:24:02Z")
After a lot of testing, and a lot of help from @thoka, I offer the following summary:
I am able to run SMTP tests using the same creds that I have supplied `container/app.yml` that work with both `swaks` ([Swaks - Swiss Army Knife for SMTP](https://jetmore.org/john/code/swaks/)) and sample Ruby code provide by @thoka (see below).
These work consistently. However, trying to standup a Discourse server (which cannot send the initial email to the admin user) or using `discourse-doctor` bot result in email failures:
```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@burlyqna.org]:
Sending mail to admin@burlyqna.org. . .
Testing sending to admin@burlyqna.org using smtp.mailfence.com:465, username:xxx@mailfence.com with plain auth.
SMTP server connection successful.
Sending to admin@burlyqna.org. . .
Sending mail failed.
end of file reached
```
This seems to be a protocol config failure, as I’m able send test emails using standard Ruby tools:
```ruby
require 'mail'
SMTP_SERVER = 'smtp.mailfence.com'
SMTP_PORT = 465
USERNAME = 'xyz'
PASSWORD = '...'
FROM = 'admin@burlyqna.org'
TO = 'testing@gmail.com'
SUBJECT = 'Test from Ruby'
BODY = "Hello,\n\nThis is a test email sent from Ruby over a SSL-secured connection.\n\nBest regards!"
Mail.defaults do
delivery_method :smtp, {
address: SMTP_SERVER,
port: SMTP_PORT,
user_name: USERNAME,
password: PASSWORD,
domain: "burlyqna.org",
enable_starttls_auto: :false,
authentication: :plain,
ssl: true,
}
end
begin
puts 'Sending email...'
puts "SMTP_SERVER: #{SMTP_SERVER}"
puts "SMTP_PORT: #{SMTP_PORT}"
puts "USERNAME: #{USERNAME}"
puts "PASSWORD: #{PASSWORD}"
puts "FROM: #{FROM}"
puts "TO: #{TO}"
mail = Mail.new do
to TO
from FROM
subject SUBJECT
body BODY
end
mail.deliver!
end
```
The current SMTP settings in my app.yml are:
```plaintext
DISCOURSE_SMTP_ADDRESS: smtp.mailfence.com
DISCOURSE_SMTP_PORT: 465
DISCOURSE_SMTP_USER_NAME: xxx@mailfence.com
DISCOURSE_SMTP_PASSWORD: '...'
DISCOURSE_SMTP_FORCE_TLS: true # https://meta.discourse.org/t/cannot-send-email-problem-with-port-465/246004/8
DISCOURSE_SMTP_ENABLE_START_TLS: false # (optional, default true)
DISCOURSE_SMTP_DOMAIN: burlyqna.org # (required by some providers)
DISCOURSE_NOTIFICATION_EMAIL: noreply@talk.burlyqna.org
```
---
### Author:  [@philion](https://meta.discourse.org/u/philion)
#### Post date: [March 13, 2025, 11:46pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/19 "2025-03-13T23:46:41Z")
Final followup: _ **email is working!** _
The problems I had along the way:
- DISCOURSE\_SMTP\_PASSWORD had symbols but wasn’t in quotes
- DISCOURSE\_SMTP\_FORCE\_TLS: true to make SSL happen
- DISCOURSE\_SMTP\_ENABLE\_START\_TLS: false to stop the TLS handshake
- DISCOURSE\_NOTIFICATION\_EMAIL set to an non-existing email address
```plaintext
DISCOURSE_SMTP_ADDRESS: smtp.mailfence.com
DISCOURSE_SMTP_PORT: 465
DISCOURSE_SMTP_USER_NAME: example@mailfence.com
DISCOURSE_SMTP_PASSWORD: 'passwd'
DISCOURSE_SMTP_FORCE_TLS: true
DISCOURSE_SMTP_ENABLE_START_TLS: false
DISCOURSE_NOTIFICATION_EMAIL: admin@example.org
```
---
### Author:  [@system](https://meta.discourse.org/u/system)
#### Post date: [April 12, 2025, 11:46pm UTC](https://meta.discourse.org/t/mail-test-failure-in-discourse-doctor/356453/20 "2025-04-12T23:46:59Z")
This topic was automatically closed 30 days after the last reply. New replies are no longer allowed.