As you say, when you use telnet port 587 (or port 25 for that matter) you get a 
plain text connection.
If you then type "EHLO whatever", you will get the capabilities of the SMTP 
server.
You will see that it contains STARTTLS capability.

I suggest that you need to remove the "Use SSL" flag.
You should also add the flag " -Dmail.smtp.starttls.enable=true" to your 
Jenkins startup configuration to cause it to start a TLS connection in response 
to the STARTTLS capability.

That should get you a TLS connection.

There is some information at http://www.tune2wizard.com/linux-jenkins/.

Chris



On 02/07/2015 13:15, [email protected] wrote:
>
> I don't know what am I doing wrong, I'm searching the net for hours. Anyways, 
> here is my e-mail setup for Jenkins. I'm not able to send any mails. When I 
> click "Test Configuration", I get the
> following error.
>
> I changed the STMP Port to 25 and still get the same error.
>
> <https://lh3.googleusercontent.com/-AnDvujXZAOo/VZUrLl5UUCI/AAAAAAAAAek/sxUAo6Or6T8/s1600/uPldQ.png>
>
> And btw I typed |telnet smtp.live.com 587| to my console ant the output was:
>
> |Trying 65.55.163.152...
> Connected to smtp.glbdns2.microsoft.com.
> Escape character is '^]'.
> 220 BLU437-SMTP76.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 
> 8.0.9200.16384 ready at  Thu, 2 Jul 2015 04:31:09 -0700 
> Connection closed by foreign host.
> |
> |
>
> What am I missing? What is the correct configuration? Thanks in advance!
>
> |
>
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