Hello, I’ve been trying to fix my smtp issue and it doesn’t send emails and when I run the ./discourse-doctor command it gives me an Net::Timeout error. Thanks in advance for the help. app.yml smtp section DISCOURSE_SMTP_ADDRESS: plesk.oxide.host DISCOURSE_SMTP_PORT: 465 DISCOURSE_SMTP_USER_NAME: no-reply@kyekillerbot.xyz DISCOURSE_SMTP_PASSWORD: password DISCOURSE_SMTP_ENABLE_START_TLS: true # (optional, default true) DISCOURSE_SMTP_AUTHENTICATION: login I have tried telnet, but it connects to the smtp domain successfully .

[image] kyekiller: DISCOURSE_SMTP_ENABLE_START_TLS: true # Have you tried commenting this line? I don’t think the port 465 supports STARTTLS

[image] kyekiller: 465 As far as port 465, see,RFC8314 [image] RFC 8314: Cleartext Considered Obsolete: Use of Transport Layer Security... This specification outlines current recommendations for the use of Transport Layer Security (TLS) to provide confidentiality of email traffic between a Mail User Agent (MUA) and a Mail Submission Server or Mail Access Server. This document updates... Based on this RFC, both ports 465 and 587 are valid ports for an SMTP mail submission agent (MSA). Port 465 requires negotiation of TLS/SSL at connection setup and port 587 uses STARTTLS if one chooses to negotiate TLS. The IANA registry has been updated to allow legitimate use of port 465 for this purpose. For an SMTP mail relay, only port 25 is used so STARTTLS is the only way to do TLS with mail relay. @kyekiller , you should consider trying this setting (set to false) if you are going to use port 465: DISCOURSE_SMTP_ENABLE_START_TLS: false Commenting it out will probably not help much, since directly from the Discourse container files, the default for this setting is true; so commenting out this line, it will still be set to true: #DISCOURSE_SMTP_ENABLE_START_TLS: true # (optional, default true) HTH See also (from RFC): When a TCP connection is established for the “submissions” service (default port 465), a TLS handshake begins immediately. Clients MUST implement the certificate validation mechanism described in [RFC7817]. Once the TLS session is established, Message Submission protocol data [RFC6409] is exchanged as TLS application data for the remainder of the TCP connection. (Note: The “submissions” service name is defined in Section 7.3 of this document and follows the usual convention that the name of a service layered on top of Implicit TLS consists of the name of the service as used without TLS, with an “s” appended.) The STARTTLS mechanism on port 587 is relatively widely deployed due to the situation with port 465 (discussed in Section 7.3). This differs from IMAP and POP services where Implicit TLS is more widely deployed on servers than STARTTLS. It is desirable to migrate core protocols used by MUA software to Implicit TLS over time, for consistency as well as for the additional reasons discussed in Appendix A. However, to maximize the use of encryption for submission, it is desirable to support both mechanisms for Message Submission over TLS for a transition period of several years. As a result, clients and servers SHOULD implement both STARTTLS on port 587 and Implicit TLS on port 465 for this transition period. Note that there is no significant difference between the security properties of STARTTLS on port 587 and Implicit TLS on port 465 if the implementations are correct and if both the client and the server are configured to require successful negotiation of TLS prior to Message Submission. Note, there are two TLS related default settings from the Discourse defaults: # smtp authentication mechanism smtp_authentication = plain # enable TLS encryption for smtp connections smtp_enable_start_tls = true # mode for verifying smtp server certificates # to disable, set to 'none' smtp_openssl_verify_mode = # force implicit TLS as per RFC 8314 3.3 smtp_force_tls = false See also: config/discourse_defaults.conf 9aeece465 # # DO NOT EDIT THIS FILE # If you need to make changes create a file called discourse.conf in this directory with your changes # On import this file will be imported using ERB # # Discourse supports multiple mechanisms for production config. # # 1. You can do nothing and get these defaults (not recommended, you should at least set hostname) # 2. You can copy this file to config/discourse.conf and amend with your settings # 3. You can pass in config from your environment, all the settings below are available. # Append DISCOURSE_ and upper case the setting in ENV. For example: # to pass in db_timeout of 200 you would use DISCOURSE_DB_TIMEOUT=200 # All settings apply to production only # connection pool size, sidekiq is set to 5, allowing an extra 3 for bg threads db_pool = 8 # ActiveRecord connection pool timeout in milliseconds This file has been truncated. show original

SMTP email issue Net::Timeout

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itsbhanusharma (Bhanu Sharma) February 18, 2021, 3:34am 2

Have you tried commenting this line? I don’t think the port 465 supports STARTTLS

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SMTP email issue Net::Timeout

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