Mutt freezes when sending email messages to @gmail.com accounts through Google's SMTP server

[simanyay]

Mutt freezes with Authenticating (LOGIN)... when I try to send a mail to some gmail.com address. Almost nothing helps for 30-40 seconds (even ^C, only ^Z and kill -9) and then it changes status to Sending in background without actually sending anything.

I guess, SMTP returns some error but I can't figure it out because I can't find any logs and debug output (-d 5) does not show anything interesting.

Here is the output of -v:

Mutt 1.5.16 (2007-06-09)
Copyright (C) 1996-2007 Michael R. Elkins and others.
Mutt comes with ABSOLUTELY NO WARRANTY; for details type `mutt -vv'.
Mutt is free software, and you are welcome to redistribute it
under certain conditions; type `mutt -vv' for details.

System: Darwin 8.10.1 (i386)
ncurses: ncurses 5.6.20061217 (compiled with 5.6)
libiconv: 1.11
Compile options:
-DOMAIN
+DEBUG
-HOMESPOOL  +USE_SETGID  +USE_DOTLOCK  +DL_STANDALONE  
+USE_FCNTL  -USE_FLOCK   -USE_INODESORT   
+USE_POP  +USE_NNTP  +USE_IMAP  +USE_SMTP  -USE_GSS  +USE_SSL_OPENSSL  -USE_SSL_GNUTLS  +USE_SASL  +HAVE_GETADDRINFO  
+HAVE_REGCOMP  -USE_GNU_REGEX  
+HAVE_COLOR  +HAVE_START_COLOR  +HAVE_TYPEAHEAD  +HAVE_BKGDSET  
+HAVE_CURS_SET  +HAVE_META  +HAVE_RESIZETERM  
+CRYPT_BACKEND_CLASSIC_PGP  +CRYPT_BACKEND_CLASSIC_SMIME  -CRYPT_BACKEND_GPGME  
-EXACT_ADDRESS  -SUN_ATTACHMENT  
+ENABLE_NLS  -LOCALES_HACK  +HAVE_WC_FUNCS  +HAVE_LANGINFO_CODESET  +HAVE_LANGINFO_YESEXPR  
+HAVE_ICONV  -ICONV_NONTRANS  -HAVE_LIBIDN  +HAVE_GETSID  +USE_HCACHE  
-ISPELL
SENDMAIL="/usr/sbin/sendmail"
MAILPATH="/var/mail"
PKGDATADIR="/opt/local/share/mutt"
SYSCONFDIR="/opt/local/etc"
EXECSHELL="/bin/sh"
-MIXMASTER
To contact the developers, please mail to <mutt-dev@mutt.org>.
To report a bug, please visit http://bugs.mutt.org/.

vvv.nntp

And here is my smtp config:

set hostname=kovalyov.net
set realname="Anton Kovalyov"
set from='Anton Kovalyov <anton@kovalyov.net>'
set use_from=yes
mailboxes =inbox

# SMTP
set smtp_url="smtps://anton@kovalyov.net:*********@smtp.gmail.com:465"

Any help is appreciated, TIA.

[simanyay]

I forgot to mention that everything is okay with messages to non-GMail boxes.

[brendan]

mutt -d2 should generate logs. I've used gmail smtp myself with no problems. Can you reproduce with 1.5.18 (or ideally, tip)?

[brendan]

I have not been able to reproduce this with any gmail combination of smtp (587), smtps (465), smtp + starttls, password embedded in URL or prompted. In the absence of a recipe to reproduce the problem, I'm closing this bug.