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From "Zev (JIRA)" <j...@apache.org>
Subject [jira] [Created] (LOG4NET-414) Implicit SSL not supported on SMTP appender
Date Thu, 02 Jan 2014 14:40:51 GMT
Zev created LOG4NET-414:

             Summary: Implicit SSL not supported on SMTP appender
                 Key: LOG4NET-414
                 URL: https://issues.apache.org/jira/browse/LOG4NET-414
             Project: Log4net
          Issue Type: Bug
          Components: Appenders
    Affects Versions: 1.2.13
         Environment: .NET 3.5 Windows 7 professional
            Reporter: Zev

It appears that implicit SMTP (SSL) is not supported. Rather only explicit SMTP (SSL) is supported.

This is due to the fact that log4net delegates mail to the System.Net.Mail.SmtpClient object
and Microsoft doesn't support it. 

The bug request is to fix the smtp appender to support both flavors.

Marked as bug instead of improvement since some providers only support port 465 (SMTP/SSL).

In my case, using port 465 with EnableSSL. This is why my send timed out. It was waiting for
the server to respond to it’s STARTTLS command, while the server was waiting for the client
to start a secure sockets connection.


Differences between implicit and explicit SMTP SSL:
With Explicit SSL, the communication (which basically is a sockets connection) starts unencrypted
on port 25 or 587 as a regular SMTP conversation, then switches to TLS (encrypted channel)
using the SMTP STARTTLS command, after which it authenticates and starts sending the email.
This is the kind of SSL that the .NET SmtpClient understands, and the only kind it understands.
It is described in this RFC (which actually talks about FTP, but the thing at issue here is
the actual SSL connection, not the protocol – FTP or SMTP – running on top of it).

With Implicit SSL, the connection starts out the whole conversation over SSL, i.e. it is encrypted
from the get go. Commonly, port 465 is used for this. Implicit SSL is NOT covered by any RFC,
it is NOT a standard, and the .NET SmtpClient does NOT understand it. 

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