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aden@amckinley:~$  cat sample_email.txt | msmtp --debug -a amckinley aden.mckinley@gmail.com
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ignoring system configuration file /etc/msmtprc: No such file or directory
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loaded user configuration file /home/aden/.msmtprc
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using account amckinley from /home/aden/.msmtprc
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host = smtp.zoho.com
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port = 587
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proxy host = (not set)
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proxy port = 0
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timeout = off
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protocol = smtp
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domain = localhost
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auth = choose
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user = aden@amckinley.me
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password = *
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passwordeval = (not set)
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ntlmdomain = (not set)
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tls = on
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tls_starttls = on
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tls_trust_file = (not set)
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tls_crl_file = (not set)
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tls_fingerprint = (not set)
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tls_key_file = (not set)
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tls_cert_file = (not set)
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tls_certcheck = off
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tls_min_dh_prime_bits = (not set)
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tls_priorities = (not set)
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auto_from = off
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maildomain = (not set)
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from = aden@amckinley.me
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add_missing_from_header = on
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add_missing_date_header = on
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remove_bcc_headers = on
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dsn_notify = (not set)
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dsn_return = (not set)
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logfile = (not set)
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syslog = (not set)
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aliases = (not set)
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reading recipients from the command line
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<-- 220 mx.zohomail.com SMTP Server ready August 15, 2017 7:25:52 PM PDT
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--> EHLO localhost
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<-- 250-mx.zohomail.com Hello localhost (159.203.4.58 (159.203.4.58))
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<-- 250-STARTTLS
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<-- 250 SIZE 53477376
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--> STARTTLS
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<-- 220 Ready to start TLS.
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TLS certificate information:
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    Owner:
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        Common Name: *.zoho.com
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    Issuer:
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        Common Name: thawte DV SSL CA - G2
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        Organization: thawte\, Inc.
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        Organizational unit: Domain Validated SSL
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        Country: US
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    Validity:
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        Activation time: Thu 01 Sep 2016 12:00:00 AM UTC
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        Expiration time: Sat 01 Sep 2018 11:59:59 PM UTC
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    Fingerprints:
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        SHA1: 10:72:1E:8E:C1:05:77:F2:27:9B:0E:12:14:27:C5:96:0F:71:2F:B6
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        MD5:  B5:F9:8A:60:4D:45:1B:7C:04:74:62:A3:49:4A:30:18
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--> EHLO localhost
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<-- 250-mx.zohomail.com Hello localhost (159.203.4.58 (159.203.4.58))
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<-- 250-AUTH LOGIN PLAIN
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<-- 250 SIZE 53477376
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--> AUTH PLAIN AGFkZW5AYW1ja2lubGV5Lm1lAEBkM25NY2s3N3h4Z2I4Zg==
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<-- 235 Authentication Successful
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--> MAIL FROM:<aden@amckinley.me>
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<-- 250 Sender <aden@amckinley.me> OK
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--> RCPT TO:<aden.mckinley@gmail.com>
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<-- 250 Recipient <aden.mckinley@gmail.com> OK
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--> DATA
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<-- 354 Ok Send data ending with <CRLF>.<CRLF>
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--> Date: Wed, 16 Aug 2017 02:25:52 +0000
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--> From: aden@amckinley.me 
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--> \ To: aden.mckinley@gmail.com 
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--> \ Subject: Hello World 
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--> \ 
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--> \ This email was sent using MSMTP via Gmail/Yahoo.
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--> \ This email was sent using MSMTP.
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--> .
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msmtp: the server sent an empty reply
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msmtp: could not send mail (account amckinley from /home/aden/.msmtprc)