I happly use blat for most of my email broadcasts, but It DOES NOT work using my GMAIL account.
-f ***@gmail.com -server smtp.gmail.com -port 587 -u ***@gmail.com -pw mypassword
Blat v3.2.17 (build : Aug 10 2016 22:32:51)
64-bit Windows, Full, Unicode
64-bit Windows, Full, Unicode
<<<getline<<< 220 smtp.gmail.com ESMTP l33sm19721722ywh.6 - gsmtp
putline>>> EHLO jerry-s9.jsiinc.com
<<<getline<<< 250-smtp.gmail.com at your service, [99.166.100.41]
<<<getline<<< 250-SIZE 35882577
<<<getline<<< 250-8BITMIME
<<<getline<<< 250-STARTTLS
<<<getline<<< 250-ENHANCEDSTATUSCODES
<<<getline<<< 250-PIPELINING
<<<getline<<< 250-CHUNKING
<<<getline<<< 250 SMTPUTF8
Sending hvpoa_body.txt to ***@hvpoa30004.com
Subject: Final Request - H.V.P.O.A. Annual Meeting Mailing - 7th Request
Login name is ***@gmail.com
Attached binary file: 2_HVPOA_OwnerExplanationLetter.pdf
Attached binary file: 3_HVPOA_Consent_Proxy.pdf
Attached binary file: 9_HVPOA_Declaration.pdf
Try number 1 of 3.
putline>>> AUTH LOGIN
<<<getline<<< 530 5.7.0 Must issue a STARTTLS command first. l33sm19721722ywh.6 - gsmtp
*** Warning *** The SMTP server does not require AUTH LOGIN.
*** Warning *** Are you sure server supports AUTH?
<<<getline<<< 530 5.7.0 Must issue a STARTTLS command first. l33sm19721722ywh.6 - gsmtp
*** Error *** The SMTP server does not like the sender name.
*** Error *** Have you set your mail address correctly?
putline>>> QUIT
<<<getline<<< 221 2.0.0 closing connection l33sm19721722ywh.6 - gsmtp