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albertito / chasquid

SMTP (email) server with a focus on simplicity, security, and ease of operation [mirror]

Home Page:https://blitiri.com.ar/p/chasquid/

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Extend how-to guide to include how to actually send email

erjoalgo opened this issue · comments

commented

I appreciate how detailed is the how-to guide to set up chasquid as an SMTP server from scratch. However, I haven't been able to get the setup to work. My smtp-check passes successfully with chasquid running on the target server:

 smtp-check example.com
2023/09/01 20:21:13 === STS policy
2023/09/01 20:21:15 Not available (lookup _mta-sts.example.com on 1.2.3.4:53: no such host)
2023/09/01 20:21:15 
2023/09/01 20:21:15 === MX: 10  mail.example.com.
2023/09/01 20:21:17 SPF pass for 1.2.3.4: matched mx
2023/09/01 20:21:17 TLS OK: TLS-1.3 - TLS_AES_128_GCM_SHA256
2023/09/01 20:21:17 
2023/09/01 20:21:17 === Success

Yet I've tried with a variety of email clients, including an nodejs smtp client, but get errors like the following:

When sending without encryption to port 25:

Error: SMTP server does not support the LOGIN authentication mechanism
    at exports.SMTPClient.authLogin (.../node_modules/smtp-client/src/index.js:375:13)
    at send (.../smtp.js:51:11)
    at process.processTicksAndRejections (node:internal/process/task_queues:95:5)

When submitting without security enabled to port 25:

node  smtp.js
[Error: 40D82ECC117F0000:error:0A00010B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:354:
] {
  library: 'SSL routines',
  reason: 'wrong version number',
  code: 'ERR_SSL_WRONG_VERSION_NUMBER'
}

Server side:

conn.go:178        SMTP.Conn 1.2.3.4:30357: Connected, mode: SMTP
. conn.go:241        SMTP.Conn 1.2.3.4:30357: -> EHLO example.com
. conn.go:294        SMTP.Conn 1.2.3.4:30357: <- 250  poweredge - Your hour of destiny has come.\n8BITMIME\nPIPELINING\nSMTPUTF8\nENHANCEDSTATUSCODES\nSIZE 52428800\nSTARTTLS\nHELP\n
. domaininfo.go:74   DomainInfo.Reload reload: loaded 0 domains

When submitting with security enabled to port 25:

[Error: 40B8AC55587F0000:error:0A00010B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:354:
] {
  library: 'SSL routines',
  reason: 'wrong version number',
  code: 'ERR_SSL_WRONG_VERSION_NUMBER'
}

Server side:

 conn.go:178        SMTP.Conn 8.8.8.8:61172: Connected, mode: SMTP
. conn.go:241        SMTP.Conn 8.8.8.8:61172: -> \x16\x03\x01\x01X\x01\x00\x01T\x03\x03]\x056�2X\t��0\x1e%\b��\x06N��퀣�
  V��\b�� \xdd\xe9<\xf1K~\xa5tm\x10\xe2\xd3\xf4\x17\x9dzl\xec\xa2\b\x0fѰ9\xb0;U\x92\xbc\xee\xa1a\x00v\x13\x02\x13\x03\x13\x01\xc0/\xc0+\xc00\xc0,\x00\x9e\xc0'\x00g\xc0(\x00k\x00\xa3\x00\x9f̨̩̪\xc0\xaf\xc0\xad\xc0\xa3\xc0\x9f\xc0]\xc0a\xc0W\xc0S\x00\xa2\xc0\xae\xc0\xac\xc0\xa2\xc0\x9e\xc0\\\xc0`\xc0V\xc0R\xc0$\x00j\xc0#\x00@\xc0
. conn.go:294        SMTP.Conn 8.8.8.8:61172: <- 500  5.5.1 Unknown command
_ conn.go:298        SMTP.Conn 8.8.8.8:61172: error: unknown<\"\\x16\\x03\\x01\\x01X\\x01\"> failed: 500  5.5.1 Unknown command
. conn.go:241        SMTP.Conn 8.8.8.8:61172: -> �\x14\x009\x008�\t�\x13\x003\x002\x00������Q\x00������P\x00=\x00<\x005\x00/\x00�\x01\x00\x00�\x00\v\x00\x04\x03\x00\x01\x02\x00 
. conn.go:294        SMTP.Conn 8.8.8.8:61172: <- 500  5.5.1 Unknown command
_ conn.go:298        SMTP.Conn 8.8.8.8:61172: error: unknown<\"�\\x14\\x009\\x008\"> failed: 500  5.5.1 Unknown command
. conn.go:241        SMTP.Conn 8.8.8.8:61172: -> \x00\x16\x00\x14\x00\x1d\x00\x17\x00\x1e\x00\x19\x00\x18\x01\x00\x01\x01\x01\x02\x01\x03\x01\x04\x00#\x00\x00\x00\x16\x00\x00\x00\x17\x00\x00\x00\r\x00*\x00(\x04\x03\x05\x03\x06\x03\b\a\b\b\b\t\b 
. conn.go:294        SMTP.Conn 8.8.8.8:61172: <- 500  5.5.1 Unknown command
_ conn.go:298        SMTP.Conn 8.8.8.8:61172: error: unknown<\"\\x00\\x16\\x00\\x14\\x00\\x1d\"> failed: 500  5.5.1 Unknown command
_ conn.go:305        SMTP.Conn 8.8.8.8:61172: error: too many errors, breaking connection

When setting listening on port 25 as the submission address instead of as the smtp server, I get a similar error:

. domaininfo.go:74   DomainInfo.Reload reload: loaded 0 domains 
E chasquid.go:195    Warning: No SMTP addresses/listeners                                                                     
E chasquid.go:196    If using systemd, check that you named the sockets                                                       
E chasquid.go:195    Warning: No submission+TLS addresses/listeners                                                           
E chasquid.go:196    If using systemd, check that you named the sockets                                                       
. sts.go:493         STSCache.Refresh /var/lib/chasquid/sts-cache: 0 entries                                                  
. sts.go:521         STSCache.Refresh /var/lib/chasquid/sts-cache: refresh done
_ server.go:218      Server listening on :25 (submission)                                                                     
. conn.go:178        SMTP.Conn 8.8.8.8:28672: Connected, mode: submission                                               . conn.go:241        SMTP.Conn 8.8.8.8:28672: -> \x16\x03\x01\x01X\x01\x00\x01T\x03\x03�^\\��L?�ߝ���;��S \x1bJQa\x00F\xc
e\xf13\x14\xb0\x81\xe5                                                                                                        
. conn.go:294        SMTP.Conn 8.8.8.8:28672: <- 500  5.5.1 Unknown command                                             _ conn.go:298        SMTP.Conn 8.8.8.8:28672: error: unknown<\"\\x16\\x03\\x01\\x01X\\x01\"> failed: 500  5.5.1 Unknown 
command                                                                                                                       . conn.go:241        SMTP.Conn 8.8.8.8:28672: ->  \xb0\xd7\xf2\xfd\x8d\xdeC\x16ݫ\xf3|V\xaby\xe3b\x10\xcb\xce)BAW\xbfq\x0f\x1b1^ˣ\x00v\x13\x02\x13\x03\x13\x01\xc0/\xc0+\xc00\xc0,\x00\x9e\xc0'\x00g\xc0(\x00k\x00\xa3\x00\x9f̨̩̪\xc0\xaf\xc0\xad\xc0\xa3\
xc0\x9f\xc0]\xc0a\xc0W\xc0S\x00\xa2\xc0\xae\xc0\xac\xc0\xa2\xc0\x9e\xc0\\\xc0`\xc0V\xc0R\xc0$\x00j\xc0#\x00@\xc0              
. conn.go:294        SMTP.Conn 8.8.8.8:28672: <- 500  5.5.1 Unknown command                                             
_ conn.go:298        SMTP.Conn 8.8.8.8:28672: error: unknown<\"\"> failed: 500  5.5.1 Unknown command                   . conn.go:241        SMTP.Conn 8.8.8.8:28672: -> �\x14\x009\x008�\t�\x13\x003\x002\x00������Q\x00������P\x00=\x00<\x005\
x00/\x00�\x01\x00\x00�\x00\v\x00\x04\x03\x00\x01\x02\x00                                                                      
. conn.go:294        SMTP.Conn 8.8.8.8:28672: <- 500  5.5.1 Unknown command                                             
_ conn.go:298        SMTP.Conn 8.8.8.8:28672: error: unknown<\"�\\x14\\x009\\x008\"> failed: 500  5.5.1 Unknown command 
_ conn.go:305        SMTP.Conn 8.8.8.8:28672: error: too many errors, breaking connection                               
. domaininfo.go:74   DomainInfo.Reload reload: loaded 0 domains                                                               
. domaininfo.go:74   DomainInfo.Reload reload: loaded 0 domains

I noticed what appears to be a warning, No submission+TLS addresses/listeners, No SMTP addresses/listeners, not sure if this is relevant since the process is indeed listenting on the port specified in the chasquid.conf file.

  1. What am I missing to be able to actually use chasquid as my SMTP server?
  2. Do you have any recommended client programs and steps to test the chasquid server email delivery? Would you consider enhancing the how-to guide to include this last but very important setup step?
commented

I appreciate how detailed is the how-to guide to set up chasquid as an SMTP server from scratch. However, I haven't been able to get the setup to work. My smtp-check passes successfully with chasquid running on the target server:

Thanks for reporting this! I think there could be a few things going on, so I'll reply part by part.

Yet I've tried with a variety of email clients, including an nodejs smtp client, but get errors like the following:

When sending without encryption to port 25:

Error: SMTP server does not support the LOGIN authentication mechanism
    at exports.SMTPClient.authLogin (.../node_modules/smtp-client/src/index.js:375:13)
    at send (.../smtp.js:51:11)
    at process.processTicksAndRejections (node:internal/process/task_queues:95:5)

This is because chasquid does not allow clients to authenticate on a non-encrypted connection.
It doesn't even advertise it until an encrypted connection is established, and that's why your client complains.

This is working as intended.

When submitting with security enabled to port 25:

[Error: 40B8AC55587F0000:error:0A00010B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:354:
] {
  library: 'SSL routines',
  reason: 'wrong version number',
  code: 'ERR_SSL_WRONG_VERSION_NUMBER'
}

This seems like your client tried to negotiate TLS directly on port 25, which is not going to work.
On ports 25 (smtp) and 587 (submission), the TLS negotiation is done after establishing a plaintext connection, using a mechanism called STARTTLS.

If you want to do a TLS connection from the beginning (which is a great idea), use port 465 ("submission over tls", also called "submissions" (note the final "s")).

When setting listening on port 25 as the submission address instead of as the smtp server, I get a similar error:

This is not going to work well. Unfortunately the different ports have slightly different semantics.

I noticed what appears to be a warning, No submission+TLS addresses/listeners, No SMTP addresses/listeners, not sure if this is relevant since the process is indeed listenting on the port specified in the chasquid.conf file.

chasquid expects 3 different listening ports configured in chasquid.conf: smtp_address, submission_address, and submission_over_tls_address.

You should set all 3. Unless you're doing something unusual, the using the examples I linked to should work just fine.

  1. What am I missing to be able to actually use chasquid as my SMTP server?

Based on the above, I think you have two problems:

  1. chasquid listening ports are misconfigured, fix that first, which should be a simple edit to the chasquid.conf file and make sure it has:
smtp_address: ":25"
submission_address: ":587"
submission_over_tls_address: ":465"
  1. You need to tell the client that you're using to connect with "security enabled" on port 465, or use a client that can do STARTTLS negotiation on ports 25 or 587.

Let me know how it goes if you try these changes!

  1. Do you have any recommended client programs and steps to test the chasquid server email delivery? Would you consider enhancing the how-to guide to include this last but very important setup step?

This is a good suggestion, I think at least a generic note on how to configure clients can be useful to prevent confusion.
I'll add something like that for sure.

chasquid should work with any reasonable client, and there's a lot of variation in what people use, but I can see if I find good generic links that I can include for people who want more detailed guides about setting up clients.

Thanks!

commented

Thanks to your pointers I was able to get a little further, my SMTP client was able to talk to the submission_over_tls_address.

(As an aside, I also had some issues with misconfigured DNS records -- My mail.example.com was a CNAME pointing to example.com, so I was getting errors like:

Error [ERR_TLS_CERT_ALTNAME_INVALID]: Hostname/IP does not match certificate's altnames: Host: example.com.com. is not in the cert's altnames: DNS:mail.example.com.com

)

Now I am running into another error, Relay not allowed:

. sts.go:480         STSCache.Refresh /var/lib/chasquid/sts-cache: 1 entries
. sts.go:488         STSCache.Refresh /var/lib/chasquid/sts-cache: gmail.com: refreshing
_ server.go:207      Server listening on :25 (SMTP)
_ server.go:207      Server listening on :465 (submission+TLS)
. sts.go:498         STSCache.Refresh /var/lib/chasquid/sts-cache: gmail.com: fetched
. sts.go:504         STSCache.Refresh /var/lib/chasquid/sts-cache: gmail.com: stored
. sts.go:508         STSCache.Refresh /var/lib/chasquid/sts-cache: refresh done
^[[A^[[A^[[A^[[A^[[A^[[A. conn.go:164        SMTP.Conn 172.56.72.246:45446: Connected, mode: submission+TLS
. conn.go:202        SMTP.Conn 172.56.72.246:45446: -> EHLO mail.example.om
. conn.go:247        SMTP.Conn 172.56.72.246:45446: <- 250  ssdnodes-81100 - Your hour of destiny has come.\n8BITMIME\nPIPELINING\nSMTPUTF8\nENHANCEDSTATUSCODES\nSIZE 52428800\nAUTH PLAIN\nHELP\n
. conn.go:200        SMTP.Conn 172.56.72.246:45446: -> AUTH <redacted>
. maillog.go:80      Authentication Incoming SMTP: 172.56.72.246:45446 auth succeeded for ealfonso@mail.example.om\n
. conn.go:247        SMTP.Conn 172.56.72.246:45446: <- 235  2.7.0 Authentication successful
. conn.go:202        SMTP.Conn 172.56.72.246:45446: -> MAIL FROM:<ealfonso@example.om>
. conn.go:459        SMTP.Conn 172.56.72.246:45446: SPF did not pass, skipping security level check
. conn.go:247        SMTP.Conn 172.56.72.246:45446: <- 250  2.1.5 You feel like you are being watched
. conn.go:202        SMTP.Conn 172.56.72.246:45446: -> RCPT TO:<erjoalgo@gmail.com>
. conn.go:247        SMTP.Conn 172.56.72.246:45446: <- 250  2.1.5 You have an eerie feeling...
. conn.go:202        SMTP.Conn 172.56.72.246:45446: -> DATA
. conn.go:565        SMTP.Conn 172.56.72.246:45446: <- 354  You experience a strange sense of peace
. conn.go:582        SMTP.Conn 172.56.72.246:45446: -> ... 124 bytes of data
. conn.go:740        Hook.Post-DATA 172.56.72.246:45446: running
_ conn.go:792        Hook.Post-DATA 172.56.72.246:45446: error: error parsing post-data output: '/usr/bin/dkimsign\n'
_ conn.go:608        SMTP.Conn 172.56.72.246:45446: Queued from ealfonso@example.om to [erjoalgo@gmail.com] - ufa0rFWa52M
. conn.go:247        SMTP.Conn 172.56.72.246:45446: <- 250  2.0.0 An invisible choir sings, and you are bathed in radiance...
_ queue.go:304       Queue.SendLoop ufa0rFWa52M: from ealfonso@example.om
. queue.go:347       Queue.SendLoop ufa0rFWa52M: erjoalgo@gmail.com sending
. smtp.go:64         Courier.SMTP erjoalgo@gmail.com: erjoalgo+fwd_from=ealfonso=example.om@gmail.com  ->  erjoalgo@gmail.com
. smtp.go:294        Courier.SMTP erjoalgo@gmail.com: MXs: [gmail-smtp-in.l.google.com. alt1.gmail-smtp-in.l.google.com. alt2.gmail-smtp-in.l.google.com. alt3.gmail-smtp-in.l.google.com. alt4.gmail-smtp-in.l.google.com.]
. sts.go:430         STSCache.Fetch gmail.com: cache hit: &{STSv1 enforce [gmail-smtp-in.l.google.com *.gmail-smtp-in.l.google.com] 24h0m0s}
. smtp.go:242        Courier.SMTP erjoalgo@gmail.com: got STS policy
. conn.go:202        SMTP.Conn 172.56.72.246:45446: -> QUIT
. smtp.go:177        Courier.SMTP erjoalgo@gmail.com: Secure - using TLS
. domaininfo.go:135  DomainInfo /var/lib/chasquid/domaininfo: gmail.com outgoing allowed: TLS_SECURE == TLS_SECURE
. smtp.go:202        Courier.SMTP erjoalgo@gmail.com: STS policy: connection is using valid TLS
_ smtp.go:220        Courier.SMTP erjoalgo@gmail.com: error: DATA closing 550 5.7.1 [1.2.3.4] Messages missing a valid messageId header are not\n5.7.1 accepted. bz25-20020a056a02061900b0055387ef9633si5886387pgb.804 - gsmtp
_ queue.go:355       Queue.SendLoop ufa0rFWa52M: error: erjoalgo@gmail.com permanent error: DATA closing 550 5.7.1 [1.2.3.4] Messages missing a valid messageId header are not\n5.7.1 accepted. bz25-20020a056a02061900b0055387ef9633si5886387pgb.804 - gsmtp         
. queue.go:434       Queue.SendLoop ufa0rFWa52M: sending DSN
_ queue.go:462       Queue.SendLoop ufa0rFWa52M: queued DSN: bEH-o2zZlxg
_ queue.go:338       Queue.SendLoop ufa0rFWa52M: all done
_ queue.go:304       Queue.SendLoop bEH-o2zZlxg: from <>
. queue.go:347       Queue.SendLoop bEH-o2zZlxg: ealfonso@example.om sending
. smtp.go:64         Courier.SMTP ealfonso@example.om: <>  ->  ealfonso@example.om
. smtp.go:294        Courier.SMTP ealfonso@example.om: MXs: [mail.example.om.]
. sts.go:437         STSCache.Fetch example.om: failed to fetch: lookup _mta-sts.example.om on 8.8.8.8:53: no such host
. conn.go:164        SMTP.Conn 1.2.3.4:49136: Connected, mode: SMTP
. conn.go:202        SMTP.Conn 1.2.3.4:49136: -> EHLO ssdnodes-81100
. conn.go:247        SMTP.Conn 1.2.3.4:49136: <- 250  ssdnodes-81100 - Your hour of destiny has come.\n8BITMIME\nPIPELINING\nSMTPUTF8\nENHANCEDSTATUSCODES\nSIZE 52428800\nSTARTTLS\nHELP\n
. conn.go:202        SMTP.Conn 1.2.3.4:49136: -> STARTTLS
. conn.go:866        SMTP.Conn 1.2.3.4:49136: <- 220  You experience a strange sense of peace
. conn.go:874        SMTP.Conn 1.2.3.4:49136: <> ...  jump to TLS was successful
. conn.go:202        SMTP.Conn 1.2.3.4:49136: -> EHLO ssdnodes-81100
. conn.go:247        SMTP.Conn 1.2.3.4:49136: <- 250  mail.example.om - Your hour of destiny has come.\n8BITMIME\nPIPELINING\nSMTPUTF8\nENHANCEDSTATUSCODES\nSIZE 52428800\nAUTH PLAIN\nHELP\n
. smtp.go:177        Courier.SMTP ealfonso@example.om: Secure - using TLS
. domaininfo.go:135  DomainInfo /var/lib/chasquid/domaininfo: example.om outgoing allowed: TLS_SECURE == TLS_SECURE
. conn.go:202        SMTP.Conn 1.2.3.4:49136: -> MAIL FROM:<> BODY=8BITMIME
. conn.go:247        SMTP.Conn 1.2.3.4:49136: <- 250  2.1.5 You feel like you are being watched
. conn.go:202        SMTP.Conn 1.2.3.4:49136: -> RCPT TO:<ealfonso@example.om>
. conn.go:247        SMTP.Conn 1.2.3.4:49136: <- 503  5.7.1 Relay not allowed
_ conn.go:251        SMTP.Conn 1.2.3.4:49136: error: RCPT failed: 503  5.7.1 Relay not allowed
_ smtp.go:206        Courier.SMTP ealfonso@example.om: error: MAIL+RCPT 503 5.7.1 Relay not allowed
_ queue.go:355       Queue.SendLoop bEH-o2zZlxg: error: ealfonso@example.om permanent error: MAIL+RCPT 503 5.7.1 Relay not allowed
_ conn.go:270        SMTP.Conn 1.2.3.4:49136: error: exiting with error: EOF
_ queue.go:338       Queue.SendLoop bEH-o2zZlxg: all done
. domaininfo.go:72   DomainInfo /var/lib/chasquid/domaininfo: loaded 2 domains
q^[[B

I haven't gotten a chance to try to understand what is going on but I wanted to update this bug in case this is related to chasquid misconfiguration.

commented

Thanks to your pointers I was able to get a little further, my SMTP client was able to talk to the submission_over_tls_address.

Great!

Now I am running into another error, Relay not allowed:

. conn.go:164        SMTP.Conn 172.56.72.246:45446: Connected, mode: submission+TLS
. conn.go:202        SMTP.Conn 172.56.72.246:45446: -> EHLO mail.example.om
. conn.go:247        SMTP.Conn 172.56.72.246:45446: <- 250  ssdnodes-81100 - Your hour of destiny has come.\n8BITMIME\nPIPELINING\nSMTPUTF8\nENHANCEDSTATUSCODES\nSIZE 52428800\nAUTH PLAIN\nHELP\n
. conn.go:200        SMTP.Conn 172.56.72.246:45446: -> AUTH <redacted>
. maillog.go:80      Authentication Incoming SMTP: 172.56.72.246:45446 auth succeeded for ealfonso@mail.example.om\n
. conn.go:247        SMTP.Conn 172.56.72.246:45446: <- 235  2.7.0 Authentication successful

Here you authenticated successfully.

_ conn.go:608 SMTP.Conn 172.56.72.246:45446: Queued from ealfonso@example.om to [erjoalgo@gmail.com] - ufa0rFWa52M

And sent an email from ealfonso@example.om to erjoalgo@gmail.com. So far, all is well.

I'm assuming the "example.om" domain is you doing some substitution, but it is correct.

_ queue.go:304 Queue.SendLoop ufa0rFWa52M: from ealfonso@example.om
_ smtp.go:220 Courier.SMTP erjoalgo@gmail.com: error: DATA closing 550 5.7.1 [1.2.3.4] Messages missing a valid messageId header are not\n5.7.1 accepted. bz25-20020a056a02061900b0055387ef9633si5886387pgb.804 - gsmtp
_ queue.go:355 Queue.SendLoop ufa0rFWa52M: error: erjoalgo@gmail.com permanent error: DATA closing 550 5.7.1 [1.2.3.4] Messages missing a valid messageId header are not\n5.7.1 accepted. bz25-20020a056a02061900b0055387ef9633si5886387pgb.804 - gsmtp

Here, gmail's SMTP server is rejecting your email.

As you can see in the error, it complains that your message is invalid because it does not have a Message-ID header. This is unrelated to chasquid (which is just passing your email along to gmail), it is something you need to fix on your client.

_ queue.go:462 Queue.SendLoop ufa0rFWa52M: queued DSN: bEH-o2zZlxg
_ queue.go:304 Queue.SendLoop bEH-o2zZlxg: from <>

Because chasquid accepted your mail, but could not deliver it to gmail (due to gmail rejecting it as mentioned above), chasquid generates a "Bounce message" (also known as DSN, Delivery Status Notification), which is an email it sends to you to let you know about the failed delivery. This is standard, and all mail servers behave this way.

. conn.go:202 SMTP.Conn 1.2.3.4:49136: -> MAIL FROM:<> BODY=8BITMIME
. conn.go:247 SMTP.Conn 1.2.3.4:49136: <- 250 2.1.5 You feel like you are being watched
. conn.go:202 SMTP.Conn 1.2.3.4:49136: -> RCPT TO:ealfonso@example.om
. conn.go:247 SMTP.Conn 1.2.3.4:49136: <- 503 5.7.1 Relay not allowed
_ conn.go:251 SMTP.Conn 1.2.3.4:49136: error: RCPT failed: 503 5.7.1 Relay not allowed
_ smtp.go:206 Courier.SMTP ealfonso@example.om: error: MAIL+RCPT 503 5.7.1 Relay not allowed
_ queue.go:355 Queue.SendLoop bEH-o2zZlxg: error: ealfonso@example.om permanent error: MAIL+RCPT 503 5.7.1 Relay not allowed

When chasquid attempts to deliver that bounce message, it is rejected because "Relay not allowed".

I suspect this is due to a misconfiguration, because you did not tell your chasquid server it is responsible for example.om.
I think it's likely you told chasquid it is responsible for mail.example.om but not example.om. This is a misconfiguration.

If your server is mail.example.com but you want to receive messages for @example.com, you need to:

  1. Set up the MX record pointing to mail.example.com.
  2. Get TLS certificates for mail.example.com.
  3. Tell chasquid to accept mail for example.com, by mkdir -p /etc/chasquid/domains/example.com

I think you've done step 3 but with mail.example.com instead of example.com.

I hope this helps!

commented

Thanks again! I hadn't noticed the first error related to the missing Message-ID header. I was able to successfully deliver to a non-gmail address, and to a gmail address after specifying the Message-Id (and strangely, sometimes this also worked without a Message-Id).

In case it is helpful to anyone, I used the following sample smtp client code to send the email:

const {SMTPClient} = require("smtp-client");

const uuid = require('uuid');


var spec = {
  from: "user@example.com",
  host: "mail.example.com",
  dest: "user@gmail.com",
  subject: "hola hola",
  port: 465,
  secure: true,
  user: "user@example.com.com",
  password: 'REDACTED',
  contents: "email contents"
}

async function send( data ) {
  console.log("email spec: " + JSON.stringify(data, 4));

  let s = new SMTPClient({
    host: data.host,
    port: data.port,
    secure: data.secure
  });

  mime = (
    `From: <${data.from}>
To: <${data.dest}>
Subject: ${data.subject}
Message-ID: ${uuid.v4()}

${data.contents}`)
  await s.connect();
  await s.greet({hostname: data.host}); // runs EHLO command or HELO as a fallback
  var auths = await s.getAuthMechanisms();
  console.log("supported auths: " + JSON.stringify(auths, 4));

  await s.authPlain({username: data.user,
                     password: data.password}); // authenticates a user
  await s.mail({from: data.from}); // runs MAIL FROM command
  await s.rcpt({to: data.dest}); // runs RCPT TO command (run this multiple times to add more recii)
  await s.data(mime); // runs DATA command and streams email source
  await s.quit(); // runs QUIT command
}

send(spec).catch(console.error);

Maybe we can close this issue and consider adding a brief troubleshooting guide at the end of the how-to at a future date?

commented

Thanks, that sounds good to me!