Matus,
Thanks for your reply. As it turns out, I am able to send for reasons that are not clear to me. My test email command called the default account (Work) which was also the .msmtprc default (Work). But where the test.email method failed, sending from the mu/mu4e client in Emacs worked. I changed nothing. So my account "works" but I don't know why. A little unsatisfying after spending so much time trying to solve this but at least my credentials are in order.
But now, I've encountered a new difficulty. My work machine is running OSX (10.9) and provides the following when I run "msmtp --v":
wills-Mac-Pro:~ wmonro1$ msmtp --v
msmtp version 1.4.32
Platform: x86_64-apple-darwin13.3.0
TLS/SSL library: OpenSSL
Authentication library: built-in
Supported authentication methods:
plain cram-md5 external login
IDN support: disabled
NLS: disabled
Keyring support: MacOS
System configuration file name: /usr/local/Cellar/msmtp/1.4.32/etc/msmtprc
User configuration file name: /Users/wmonro1/.msmtprc
Note the lack of ntlm authentication in the supported authentication methods. Does anyone have advice on how to troubleshoot the installation of msmtp so that it supports NTLM on OSX? I've been using brew to install msmtp which provides the following, very terse feedback:
==> ./configure --with-macosx-keyring --prefix=/usr/local/Cellar/msmtp/1.4.32 --with-ssl=openssl