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It should be
EHLO
get response check to make sure STRTLS is there...
STRTLS
check response
EHLO
get response and make sure AUTH LOGIN is an option
AUTH LOGIN
check for userid prompt (base64)
send user id base64
check for password prompt (base64)
send password in base64

I know you're probably not going to check the responses, but that's how
it's supposed to work. :) There is more to it than just the bare
minimum... but that's what most seem to go for.

If you want to contact me offline to see if I can get MAILTOOL Plus to work
with it just to make sure the SMTP server isn't for some reason wacky, feel
free.

Brad
www.bvstools.com

On Thu, Dec 15, 2022 at 2:41 AM Don Brown via MIDRANGE-L <
midrange-l@xxxxxxxxxxxxxxxxxx> wrote:

Thank you for your help.

OK we have progress and can now send an email successfully.

We had not enabled STARTTLS


We are now trying to enable STARTTLS and here is the log up to where it
fails.

Connection to mail.smtp2go.com established
220 mail.smtp2go.com ESMTP Exim 4.96-S2G Thu, 15 Dec 2022 08:36:35 +0000
EHLO MSD820.MSD.LOCAL
250-mail.smtp2go.com Hello MSD820.MSD.LOCAL [60.241.111.51]
250-SIZE 52428800
250-8BITMIME
250-DSN
250-PIPELINING
250-PIPECONNECT
250-AUTH CRAM-MD5 PLAIN LOGIN
250-CHUNKING
250-STARTTLS
250-PRDR
250 HELP
STARTTLS
220 TLS go ahead

All good so far but all the following fail as Invalid Reply

AUTH LOGIN

EHLO MSD820.MSD.LOCAL

I am trying to find what command I should send after the 220 TLS go ahead

Any suggestions appreciated.

Thanks

Don




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