So defined that normal password in Thunderbird means PLAIN as I see from the 
logs my ASSP tries to log using LOGIN. Regardless looking at the supported AUTH 
list they are all supported:

AUTH PLAIN LOGIN DIGEST-MD5 CRAM-MD5

Thunderbird does work with the same username and password I'm using in ASSP so 
they are correct indeed. Can this be a char encoding issue or something? Or can 
ASSP be forced to use PLAIN perhaps?

Don't know what to think about any more...

Did anybody ever used MailJet with ASSP? It's a free service to send up to 200 
email/day perfect for personal usage.


________________________________
From: James Moe via Assp-user <assp-user@lists.sourceforge.net>
Sent: 04 June 2020 10:02 PM
To: For Users of ASSP <assp-user@lists.sourceforge.net>
Cc: James Moe <ji...@sohnen-moe.com>
Subject: Re: [Assp-user] TLS outbound

On 2020-06-04 5:53 AM, Ercolino De Spiacico wrote:

> 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.
>
  "Normal Password" means authentication is done in the clear. Not really a
problem if a secure connection is established previously, which your log shows
is the case.
  Are you sure the name/pass are EXACTLY the same?

> 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?
>
  Yes. Tell Thunderbird to use anything except "Normal Password." "Encrypted
Password" is a reasonable choice. (Although "OAuth2" might be a challenge to 
setup.)

--
James Moe
moe dot james at sohnen-moe dot com
520.743.3936
Think.


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