Thank you, so here's the score. the SMTP provider gives this:

[root@centos8 assp]# telnet in-v3.mailjet.com 25
Trying 104.199.96.85...
Connected to in-v3.mailjet.com.
Escape character is '^]'.
220 in.mailjet.com ESMTP Mailjet
EHLO test.com
250-smtpin.mailjet.com
250-PIPELINING
250-SIZE 15728640
250-VRFY
250-ETRN
250-STARTTLS
250-AUTH PLAIN LOGIN DIGEST-MD5 CRAM-MD5
250-AUTH=PLAIN LOGIN DIGEST-MD5 CRAM-MD5
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 SMTPUTF8

I have set the the ASSP RelayHost to:
SSL:in-v3.mailjet.com:587
populated the RelayAuthUser and RelayAuthPass accordingly, and I now get this 
error in the ASSP logs:

Jun-04-20 13:31:36 m1-73895-03416 [Worker_1] [TLS-out] 46.x.x.252 info: 
authentication - login is used
Jun-04-20 13:31:43 m1-73895-03416 [Worker_1] [TLS-out] 46.x.x.252 [SMTP Error] 
535 5.7.8 Error: authentication failed: UGFzc3dvcmQ6
The very same RelayHost:port + username/password works just fine if I set this 
directly in e.g. Thunderbird selecting "Normal Password" whatever that means 
but I guess is the same as LOGIN.

I'm confused because MailJet as per output above says to support many 
authentication mechanism including LOGIN but eventually it doesn't like it. Is 
there any way to force a different AUTH mechanism outbound in the RelayHost 
setup of ASSP?

Or am I perhaps looking in the wrong place to fix this?
Thank!

________________________________
From: Thomas Eckardt <thomas.ecka...@thockar.com>
Sent: 02 June 2020 05:55 AM
To: For Users of ASSP <assp-user@lists.sourceforge.net>
Subject: Re: [Assp-user] TLS outbound

assp is man in the middle - both connections are handled independent - assp 
tries to use the highest possible encryption mode for each connection

Thomas





Von:        "Ercolino De Spiacico" <bellocar...@hotmail.com>
An:        "assp-user@lists.sourceforge.net" <assp-user@lists.sourceforge.net>
Datum:        01.06.2020 13:31
Betreff:        [Assp-user] TLS outbound
________________________________



I have been trying to set up ASSP to use MailJet outbound. I have two questions 
in regards:

1) say I have postfix using ASSP as relay host and sends standard emails on 
port 25, if ASSP is set up with doTLS and relay hosts with TLS details is this 
meant to work end to end or do I really have to have the same communication 
type "postfix -> ASSP"  as well as "ASSP -> MailJet" ? e,g, both must plain or 
TLS but not a mix-and-match right?

2) regardless of the first question, as a test I have set both connection to be 
TLS, my emails stay in the postfix queue with the following ASSP log errors 
(SSLDebug Levl 3):
Jun-01-20 12:14:06 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:1638: don't start 
handshake: IO::Socket::SSL=GLOB(0xa12afa0)
Jun-01-20 12:14:06 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:1031: no socket 
yet
Jun-01-20 12:14:06 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:1033: accept 
created normal socket IO::Socket::SSL=GLOB(0x7efd2ec084d8)
Jun-01-20 12:14:06 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:1043: will not 
start SSL handshake yet
Jun-01-20 12:14:06 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:1061: starting 
sslifying
Jun-01-20 12:14:06 [Worker_1] SSL-DEBUG: .../IO/Socket/SSL.pm:1109: 
Net::SSLeay::accept -> -1
Jun-01-20 12:14:11 [Worker_1] Error: Worker_1 accept_SSL to client 127.0.0.1 
failed IO::Socket::SSL=GLOB(0xa12afa0) (timeout: 5 s) : SSL wants a read first

also mailq adds some extra info.

root@centos7~# mailq
-Queue ID- --Size-- ----Arrival Time---- -Sender/Recipient-------
A6E1D1260FC      691 Mon Jun  1 12:14:05  sen...@xxxxxxxxx.xxx
(lost connection with 127.0.0.1[127.0.0.1] while receiving the initial server 
greeting)
                                         destinat...@yyyyyyy.yyy

Thanks
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