Sending email from alpine through hotmail

Posted: January 3, 2012 in Uncategorized
Tags: , , , , , ,

Configuring the alpine email client to send email through the hotmail mail servers for an alternate role was more difficult than I was expecting.

The issues I encountered can be summarized as

  1. Make sure that ‘PLAIN’ does not show up in the disable-these-authenticators setting of your .pinerc file. Hotmail supports PLAIN and LOGIN SMTP authentication. Alpine will disable LOGIN authentication if the server supports PLAIN. This means that if your config file has disabled PLAIN then you don’t have any valid authenticators
  2. Do not specify the /secure option on the options list for your SMTP server. PLAIN authentication is not considered ‘secure’ by alpine (even if your connection uses ssl or tls).

The configuration I used to create an alternate role in Pine to send email through my own domain is:

LIT:pattern=”/NICK=steve/” action=”/ROLE=1/FROM=Steve Singer /\/tls\/”

This is after I’ve setup a free hotmail account to manage my domain ( at


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