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:


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:


since TLS is implemented by default.

Any suggestions?

  • Sending error: 250 means authentication error. 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. 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. 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

I got "Mail not sent. Sending error: 250" from the alpine e-mail program today. After much ado, I discovered that one of the lines of the e-mail (composed with linux's visual editor vi) exceeded an e-mail line-length limit (1000 characters or so). I broke the line in half, and the e-mail went just fine.

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