# Alpine with hotmail | SMTP | cannot send email

Dear Unix and Linux Community,

I would like to use my hotmail account through alpine. I am using the POP3 protocol, and I am able to access the email from my Inbox.

However, I am unable to send any email directly through alpine. Upon trying to send an email, I obtain the following message:

   [Sending mail |      100%    |]
[Mail not sent. Sending error: 250 2.0.0 Resetting]


I am currently accessing the following SMTP server:

    smtp-mail.outlook.com:587/pop3/user=myemail@hotmail.com


I have also tried port 25 to no avail. Occasionally it gets stuck, displaying the following:

    [Sending mail |      0%    |]


Using the TLS encryption explicitly gives the same error message:

    smtp-mail.outlook.com:587/user=myemail@hotmail.com/tls


since TLS is implemented by default.

Any suggestions?

• Sending error: 250 means authentication error. – D'Arcy Nader Apr 16 '18 at 20:20

change the customized headers field or it won't work. quoting from Alpine Faq:

From Alpine's [M]AIN MENU, choose [S]etup, then [C]onfig. Move down to the Customized Headers option. Press "A Add Value". Use the format:

    From: "My Real Name" <myusername@hotmail.com>


although i used the key C ( means change values ) to change the value and W ( where is ) to find customized headers faster.

• I forgot to add that I had already tried that one. Using smtp-mail.outlook.com:587/user=myemail@hotmail.com/tls gives the same error message as stated in the question. According to [this] (washington.edu/alpine/tech-notes/config-notes.html), the tls encryption is used by default. By adding it explicitly ones just makes sure that in the case the communication fails no insecure connection is tried. – Beubeu Apr 16 '18 at 22:06
• i think it's better to edit your question and add that. – D'Arcy Nader Apr 17 '18 at 7:01
• Done. Do you have any other idea on what could cause the problem? – Beubeu Apr 17 '18 at 10:16
• yes i have, i did it. i'm editing the answer right now. – D'Arcy Nader Apr 18 '18 at 19:38
• It worked! Thanks for your time. Do you know what was Alpine doing? I thought the user=myemail@hotmail.com string in the SMTP server specification was enough. – Beubeu Apr 19 '18 at 7:17