8000 Unable to send mail after upgrading to Debian 12 / Snipe-It 7.0.11 - Error "Unable to connect with STARTTLS" · Issue #15457 · grokability/snipe-it · GitHub
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Unable to send mail after upgrading to Debian 12 / Snipe-It 7.0.11 - Error "Unable to connect with STARTTLS" #15457
@angerized

Description

@angerized

Debug mode

Describe the bug

Hello,

I decided to open a new issue, sorry if this is a duplicate, but I think that it is a bit different than #14991.

Mail can not be sent after upgrading from Debian 11 and Snipe-It 6.something to Debian 12 and Snipe-It 7.0.11.

I am using an internal anonymous relay connector on our Exchange, on port 25 that worked fine until the update.

When running "php artisan snipeit:expiring-alerts" I get this error:

There are 2 assets with warranties expiring in the next 90 days.

Symfony\Component\Mailer\Exception\TransportException

Unable to connect with STARTTLS.

at vendor/symfony/mailer/Transport/Smtp/EsmtpTransport.php:153
149▕ if (!$stream->isTLS() && \defined('OPENSSL_VERSION_NUMBER') && \array_key_exists('STARTTLS', $this->capabilities)) {
150▕ $this->executeCommand("STARTTLS\r\n", [220]);
151▕
152▕ if (!$stream->startTLS()) {
➜ 153▕ throw new TransportException('Unable to connect with STARTTLS.');
154▕ }
155▕
156▕ $response = $this->executeCommand(sprintf("EHLO %s\r\n", $this->getLocalDomain()), [250]);
157▕ $this->capabilities = $this->parseCapabilities($response);

  +16 vendor frames

17 app/Console/Commands/SendExpirationAlerts.php:58
Illuminate\Support\Facades\Facade::__callStatic()
+12 vendor frames

30 artisan:33
Illuminate\Foundation\Console\Kernel::handle()

I tried editing the .env and add the "MAIL_TLS_VERIFY_PEER=false", but it is still the same.

I cleared my cache and so on, the issue seems to come from the connector falsely advertising STARTTLS or something, and Symfony enforcing it.

There seems to be a new parameter in Symfony 7.1 to disable auto_tls:
https://symfony.com/doc/current/mailer.html#disabling-automatic-tls

Could there be an .env variable to reflect this setting?

Installation Symfony's Mailer & Mime components form a powerful system for creating and sending emails - complete with support for multipart messages, Twig integration, CSS inlining, file attachme…

Reproduction steps

  1. Email working fine on Debian 11 / Snipe-It 6
  2. Upgrade Debian 11 to 12
  3. Upgrade Snipe-It 6 to 7.0.11 using the regular process
  4. Test email using UI -> FAILED
  5. Test email using CLI -> FAILED

Expected behavior

Email should work as before.

Screenshots

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Snipe-IT Version

7.0.11

Operating System

Debian 12

Web Server

Apache

PHP Version

8.2.20

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