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Hello James,

Am 25.10.2022 um 19:05 schrieb James H. H. Lampert via MIDRANGE-L <midrange-l@xxxxxxxxxxxxxxxxxx>:

10/25/22 12:04:02 003B Connected to Server SMTP-RELAY.GMAIL.COM(
10/25/22 12:04:02 003B ):587
10/25/22 12:04:02 0040 Relay already in processing, skip it
10/25/22 12:04:04 003F Marking jamesl@xxxxxxxxxxxxxxxxx as NDL
10/25/22 12:04:04 003F Marking jhhl@xxxxxxxxx as NDL

In between those lines, I'd expect to have a log entry with feedback information from the remote (Google) server. This information (IMO) is crucial to understand what's going on. Examples:

250 2.0.0 Ok: queued as B49DE280B39

530 5.7.0 Must issue a STARTTLS command first. g6-20020a170906594600b0072a881b21d8sm1900165ejr.119 - gsmtp

530-5.7.0 Authentication Required. Learn more at
530 5.7.0 https://support.google.com/mail/?p=WantAuthError u11-20020aa7d98b000000b00459cd13fd34sm2219514eds.85 - gsmtp

Any chance to somehow set the SMTP client ("initator") part of IBM i into debug mode, hopefully providing this feedback? Communications dump before encryption takes place? I'm sailing in unknown waters here.

I've also found this, maybe it helps you to adjust your settings to get more helpful information?


Since you're using TLS and Google enforces TLS, doing a man in the middle decryption would be a way to obtain the complete SMTP transcript, but it's a lot of work setting this up from zero.

Message ID: <635...SMTPIN_ADDED_REJECT_SESSION_161310@xxxxxxxxxxxx>

Hm. Smells a bit like both sides can't agree on a common set of crypto parameters.

:wq! PoC

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