smtps://smtp.office365.com:587 CONNECT_CR_SRVR_HELLO:wrong version number

[Roman Neuhauser]

hello,

i'm having trouble setting up mutt for SMTP submission to office365.com.
the error message is:

SSL failed: error:1400410B:SSL routines:CONNECT_CR_SRVR_HELLO:wrong version number

my configuration is:

set my_addr = "***@..."
set my_pass = "..."

set smtp_url = "smtps://$***@smtp.office365.com:587"
set smtp_pass = "$my_pass"

the IMAP(S) side of things works.

BTW, `openssl s_client -starttls smtp -connect smtp.office365.com:587`
on the same machine gives me the following output:

[...]
SSL handshake has read 3832 bytes and written 373 bytes
---
New, TLSv1/SSLv3, Cipher is ECDHE-RSA-AES256-GCM-SHA384
Server public key is 2048 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
Protocol : TLSv1.2
Cipher : ECDHE-RSA-AES256-GCM-SHA384
Session-ID:
F0180000182FEF77665B38703A449871173C25E8735A0FB1B7158F8287BA99D4
Session-ID-ctx:
Master-Key:
9C91B432BEC0273FFE252AD602420CD291B310FDD85B65788857D0D4E7B87238A928B89FBD10D4DD11EA5D68E7B594B9
Start Time: 1533721667
Timeout : 7200 (sec)
Verify return code: 0 (ok)
---
250 SMTPUTF8


`openssl version` says:

LibreSSL 2.7.4

`mutt -v` says:

Mutt 1.10.1 (2018-07-13)
Copyright (C) 1996-2016 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: Linux 4.17.9_1 (x86_64)
ncurses: ncurses 6.1.20180127 (compiled with 6.1)
libidn: 1.34 (compiled with 1.34)
hcache backend: GDBM version 1.16. 27/06/2018 (built Jul 16 2018 08:54:52)

Compiler:
Using built-in specs.
COLLECT_GCC=/usr/bin/cc
COLLECT_LTO_WRAPPER=/usr/lib/gcc/x86_64-unknown-linux-gnu/7.3.0/lto-wrapper
Target: x86_64-unknown-linux-gnu
Configured with: /builddir/gcc-7.3.0/configure --build=x86_64-unknown-linux-gnu
--enable-fast-character --prefix=/usr --mandir=/usr/share/man --infodir=/usr/
share/info --libexecdir=/usr/lib --libdir=/usr/lib --enable-threads=posix
--enable-__cxa_atexit --disable-multilib --with-system-zlib --enable-shared
--enable-lto --enable-vtable-verify --enable-linker-build-id
--enable-serial-configure --disable-werror --disable-nls --enable-default-pie
--enable-default-ssp --enable-checking=release --disable-libstdcxx-pch
--with-isl --with-linker-hash-style=gnu --disable-libunwind-exceptions
--disable-target-libiberty --with-default-libstdcxx-abi=gcc4-compatible
--enable-languages=c,c++,objc,obj-c++,fortran,lto,go
Thread model: posix
gcc version 7.3.0 (GCC)

Configure options: '--prefix=/usr' '--sysconfdir=/etc' '--sbindir=/usr/bin'
'--bindir=/usr/bin' '--mandir=/usr/share/man' '--infodir=/usr/share/info'
'--localstatedir=/var' '--enable-pop' '--enable-imap' '--enable-smtp'
'--enable-hcache' '--enable-gpgme' '--with-regex' '--with-idn' '--with-ssl'
'--with-sasl' '--enable-sidebar' '--with-gpgme-prefix=/usr' '--sysconfdir=/etc/mutt'
'--with-gdbm=/usr' 'mutt_cv_regex_broken=no' '--host=x86_64-unknown-linux-gnu'
'--build=x86_64-unknown-linux-gnu' 'build_alias=x86_64-unknown-linux-gnu'
'host_alias=x86_64-unknown-linux-gnu' 'CC=cc'
'CFLAGS=-D_FORTIFY_SOURCE=2 -mtune=generic -O2 -pipe -g'
'LDFLAGS=-Wl,-z,relro -Wl,-z,now -Wl,--as-needed ' 'CPPFLAGS= ' 'CPP=cpp'

Compilation CFLAGS: -Wall -pedantic -Wno-long-long -D_FORTIFY_SOURCE=2 -mtune= generic -O2 -pipe -g

Compile options:
-DOMAIN
-DEBUG
-HOMESPOOL -USE_SETGID +USE_DOTLOCK -DL_STANDALONE +USE_FCNTL -USE_FLOCK

+USE_POP +USE_IMAP +USE_SMTP
+USE_SSL_OPENSSL -USE_SSL_GNUTLS +USE_SASL -USE_GSS +HAVE_GETADDRINFO
-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 +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_LIBIDN2 +HAVE_GETSID
+USE_HCACHE +USE_SIDEBAR -USE_COMPRESSED
-ISPELL
SENDMAIL="/usr/sbin/sendmail"
MAILPATH="/var/mail"
PKGDATADIR="/usr/share/mutt"
SYSCONFDIR="/etc/mutt"
EXECSHELL="/bin/sh"
-MIXMASTER

any ideas?

[Michael Wagner]

Post by Roman Neuhauser
hello,
i'm having trouble setting up mutt for SMTP submission to office365.com.
SSL failed: error:1400410B:SSL routines:CONNECT_CR_SRVR_HELLO:wrong version number
set my_pass = "..."
set smtp_pass = "$my_pass"
the IMAP(S) side of things works.
BTW, `openssl s_client -starttls smtp -connect smtp.office365.com:587`

Hello Roman,

Set

set smtp_url = "smtp://$***@smtp.office365.com:587"

in your .muttrc

Hth Michael

[Roman Neuhauser]

Post by Roman Neuhauser
i'm having trouble setting up mutt for SMTP submission to office365.com.
SSL failed: error:1400410B:SSL routines:CONNECT_CR_SRVR_HELLO:wrong version number
set my_pass = "..."
set smtp_pass = "$my_pass"

hello Michael,

many thanks for the tip, this let me past the protocol version hurdle.

next up was "No authenticators available", caused by missing SASL
modules (i had libsasl installed but cyrus-sasl-modules was missing).

it's working now. thanks again,