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I'm trying to send an email with netcat, this is what i get:
****-MacBook-Pro:~ ***$ nc smtp.gmail.com 25
220 mx.google.com ESMTP h8sm66301168eew.16 - gsmtp
Helo gmail.com
250 mx.google.com at your service
MAIL FROM: <******@gmail.com>
530 5.7.0 Must issue a STARTTLS command first. h8sm66301168eew.16 - gsmtp
what is STARTTLS command and what do i need to do with it?
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Correcting SMTP settings For example, when one of customers reported “SMTP: STARTTLS failed” error in their mail app, our Support Engineers had to put “ssl://” in front of the SMTP server name. This fixed the problem and the mail started working.
To enable Outbound TLS connection in IIS SMTP Server, Open Internet Information Service (IIS) 6.0 Manager. Select a SMTP Virtual Server -> Right Click -> Properties -> Delivery -> Outbound Security -> Check TLS encryption -> Click OK -> Click Apply .
But what is StartTLS? StartTLS is a protocol command used to inform the email server that the email client wants to upgrade from an insecure connection to a secure one using TLS or SSL. StartTLS is used with SMTP and IMAP, while POP3 uses the slightly different command for encryption, STLS.
STARTTLS is an email protocol command that tells an email server that an email client, including an email client running in a web browser, wants to turn an existing insecure connection into a secure one.
STARTTLS is an extension to plain text communication protocols, which offers a way to upgrade a plain text connection to an encrypted (TLS or SSL) connection instead of using a separate port for encrypted communication.
http://en.wikipedia.org/wiki/STARTTLS
The smtp server is saying it won't accept plain text connections.
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