Discussion:
Mutt 1.10.0 -- Native SMTP -- Unable to authenticate and send mail
q***@email.com
2018-06-25 08:03:48 UTC
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Initially we used the PkgDir provided with CygWin to install mutt. After
repeated failures with this same issue, we compiled our own mutt,
resulting with the same, exact and continuing smtp failures. From the
mutt UI, the errors are:

AUTHENTICATING (LOGIN) ...
SASL authentication failed

Please consider the following output:

$ mutt -v |more
Mutt 1.10.0 (2018-05-17)
System: CYGWIN_NT-6.1 2.10.0(0.325/5/3) (x86_64)

Configure options: '--enable-smtp' '--enable-imap' '--enable-de
bug' '--enable-locales-fix' '--with-curses' '--with-regex' '--w
ith-mailpath=/home/User/' '--with-gss' '--with-ssl' '--with-sasl
' '--with-libiconv-prefix' '--with-included-gettext'

Compile options:
-DOMAIN
+DEBUG
-HOMESPOOL  -USE_SETGID  -USE_DOTLOCK  -DL_STANDALONE  +USE_FCN
TL  -USE_FLOCK
-USE_POP  +USE_IMAP  +USE_SMTP
+USE_SSL_OPENSSL  -USE_SSL_GNUTLS  +USE_SASL  +USE_GSS  +HAVE_G
ETADDRINFO
-HAVE_REGCOMP  +USE_GNU_REGEX
+HAVE_COLOR  +HAVE_START_COLOR  +HAVE_TYPEAHEAD  +HAVE_BKGDSET

+HAVE_CURS_SET  +HAVE_META  +HAVE_RESIZETERM  +HAVE_FUTIMENS
+CRYPT_BACKEND_CLASSIC_PGP  +CRYPT_BACKEND_CLASSIC_SMIME  -CRYP
T_BACKEND_GPGME
-EXACT_ADDRESS  -SUN_ATTACHMENT
+ENABLE_NLS  +LOCALES_HACK  +HAVE_WC_FUNCS  +HAVE_LANGINFO_CODE
SET  +HAVE_LANGINFO_YESEXPR
+HAVE_ICONV  -ICONV_NONTRANS  -HAVE_LIBIDN  -HAVE_LIBIDN2  +HAV
E_GETSID  -USE_HCACHE  -USE_SIDEBAR  -USE_COMPRESSED
-ISPELL
SENDMAIL="/usr/sbin/sendmail"
MAILPATH="/home/User/"
PKGDATADIR="/usr/local/share/mutt"
SYSCONFDIR="/usr/local/etc"
EXECSHELL="/bin/sh"
-MIXMASTER

END mutt -v

$ mutt -D | grep -i ssl
ssl_client_cert=""
ssl_force_tls is set
ssl_starttls=yes
ssl_use_sslv2 is unset
ssl_use_sslv3 is unset
ssl_use_tlsv1 is set
ssl_use_tlsv1_1 is set
ssl_use_tlsv1_2 is set
ssl_usesystemcerts is set
ssl_verify_dates is set
ssl_verify_host is set
ssl_verify_partial_chains is unset
ssl_ciphers=""

$ mutt -D | grep -i imap
imap_authenticators=""
imap_check_subscribed is unset
imap_delim_chars="/."
imap_headers=""
imap_idle is unset
imap_keepalive=300
imap_list_subscribed is unset
imap_login=""
imap_pass="Password"
imap_passive is set
imap_peek is set
imap_pipeline_depth=15
imap_poll_timeout=15
imap_servernoise is set
imap_user="***@Domain.Tld"

$ mutt -D | grep -i smtp
smtp_authenticators=""
smtp_pass="Password"
smtp_url="smtps://***@smtp.Domain.Tld:465/"

# OUR CURRENT ~/.mutt/muttrc
set ssl_starttls=yes
set ssl_force_tls=yes
set certificate_file=~/.mutt/certificates
set imap_user   = ***@domain.tld
set imap_pass   = "PASSWORD"
set folder      = imap://imap.domain.tld
set spoolfile   = imap://imap.domain.tld/Inbox
set postponed    = imap://imap.domain.tld/Drafts
set record    = imap://imap.domain.tld/Sent
mailboxes       = +Inbox

# SENDING MAIL
set smtp_url = "smtps://***@smtp.domain.tld:465/"
set smtp_pass = PASSWORD

END ~/.mutt/muttrc

### Using: mutt -d 2, the following is an excerpt from ~/.muttdebug0.
Using tail -f ~/.muttdebug0, after pressing the 'y' to send the mail
results in this following transaction (SMTP).

[2018-06-24 15:27:20] Sending message...
[2018-06-24 15:27:20] 6> a0009 UID STORE 4143 +FLAGS.SILENT (\Deleted)

a0010 CLOSE

a0011 STATUS "Sent" (UIDVALIDITY)

[2018-06-24 15:27:20] 6< a0009 OK UID STORE completed
[2018-06-24 15:27:20] 6< a0010 OK CLOSE completed
[2018-06-24 15:27:20] 6< * STATUS Sent (UIDVALIDITY 1386474110)
[2018-06-24 15:27:20] 6< a0011 OK STATUS completed
[2018-06-24 15:27:20] Uploading message... 0/323 (0%)
[2018-06-24 15:27:20] 6> a0012 APPEND "Sent" (\Seen) "24-Jun-2018
15:27:20 -0400" {323}

[2018-06-24 15:27:21] 6< + Ready for literal data
[2018-06-24 15:27:21] 6> Date: Sun, 24 Jun 2018 15:27:20 -0400

From: "U-Machine\\User" <***@Machine>

To: ***@Domain.Tld

Subject: aaaaaaaaaaa

Message-ID: <***@Machine>

MIME-Version: 1.0

Content-Type: text/plain; charset=us-ascii

Content-Disposition: inline

User-Agent: Mutt/1.10.0 (2018-05-17)

AAAAAAAAAAA:WQ

[2018-06-24 15:27:21] 6>

[2018-06-24 15:27:21] 6< a0012 OK [APPENDUID 1386474110 2153] APPEND
completed
[2018-06-24 15:27:21] mx_close_message (): unlinking
/tmp/mutt-Machine-197608-5916-5928701021069297487
[2018-06-24 15:27:21] Looking up smtp.Domain.Tld...
[2018-06-24 15:27:21] Connecting to smtp.Domain.Tld...
[2018-06-24 15:27:21] ssl_load_certificates: loading trusted certificates
[2018-06-24 15:27:21] ssl_verify_callback: checking cert chain entry
/C=US/O=thawte, Inc./OU=Certification Services Division/OU=(c) 2006
thawte, Inc. - For authorized use only/CN=thawte Primary Root CA
(preverify: 1 skipmode: 0)
[2018-06-24 15:27:21] ssl_verify_callback: checking cert chain entry
/C=US/O=thawte, Inc./CN=thawte SSL CA - G2 (preverify: 1 skipmode: 0)
[2018-06-24 15:27:21] ssl_verify_callback: checking cert chain entry
/C=US/ST=Pennsylvania/L=Chesterbrook/O=1&1 Mail & Media
Inc./CN=smtp.Domain.Tld (preverify: 1 skipmode: 0)
[2018-06-24 15:27:21] ssl_verify_callback: hostname check passed
[2018-06-24 15:27:22] TLSv1.2 connection using TLSv1/SSLv3
(ECDHE-RSA-AES256-GCM-SHA384)
[2018-06-24 15:27:23] Connected to smtp.Domain.Tld:465 on fd=7
[2018-06-24 15:27:23] 7< 220 gmx.com (mrgmxus001) Nemesis ESMTP Service
ready
[2018-06-24 15:27:23] 7> EHLO Machine

[2018-06-24 15:27:24] 7< 250-gmx.com Hello Machine [172.58.200.54]
[2018-06-24 15:27:24] 7< 250-AUTH LOGIN PLAIN
[2018-06-24 15:27:24] 7< 250 SIZE 141557760
[2018-06-24 15:27:24] SASL local ip: 192.168.43.12;54368, remote
ip:74.208.5.15;465
[2018-06-24 15:27:24] External SSF: 256
[2018-06-24 15:27:24] External authentication name: User
[2018-06-24 15:27:24] Authenticating (LOGIN)...
[2018-06-24 15:27:24] 7> AUTH LOGIN

[2018-06-24 15:27:24] 7< 334 VXNlcm5hbWU6
[2018-06-24 15:27:24] mutt_sasl_cb_authname: getting authname for
smtp.Domain.Tld:465
[2018-06-24 15:27:24] mutt_sasl_cb_pass: getting password for
***@smtp.Domain.Tld:465
[2018-06-24 15:27:24] 7> Q0RMLUE=

[2018-06-24 15:27:24] 7< 334 UGFzc3dvcmQ6
[2018-06-24 15:27:24] 7> MTYxMTcwOENETA==

[2018-06-24 15:27:24] 7< 535 Authentication credentials invalid
[2018-06-24 15:27:24] SASL authentication failed

END EXCERPT.

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