An error when sending an email from outlook using the telnet command

Question

I'm trying to send an email from my @outlook account to my gmail account.

SEND:    `telnet smtp.live.com 587`. I am connected. 
SEND: `   HELO blu169.mail.live.com`. 
RECEIVE: `250 BLU0-SMTP371.phx.gbl Hello [IP ADDRESS]`. 
SEND: `   MAIL FROM: myemail@outlook.com` 
RECEIVE: `530 5.7.0 Must issue a STARTTLS command first`

What kind of a STARTTLS command must I enter?

Are there other commands in the next few commands that I must enter that deviate from the basic protocols of sending an email using telnet?

Thank you.

Answer 1

You must authenticate yourself to use smtp.live.com:587 (SMTP AUTH ).

smtp.live.com:587 offers only plain text authentications methods ( LOGIN and PLAIN ) in response to EHLO (Extended HeLO) issued after turning encryption on ( STARTTLS ). The offered authentication methods are NOT secure over unencrypted "open internet" SMTP connection.

So the message means: You must issue a STARTTLS command to be able to issue required AUTH command.

Answer 2

“工具->帐户设置”，然后双击“电子邮件帐户”，然后单击“更多设置”->“高级”选项卡，将加密设置为“自动”