sorry for the late reply. I was on vacation. 
Unfortunately, I returned and could not find the managed switch anymore.
Someone must've taken it. So I won't be able to post a .pcap file, since I
cannot remote capture.

However, it seems I managed to get rid of the "unknown protocol" error. I
was using the read function of my colleague and it was only copying bytes
until it reaches a newline character, so when I call the TLS function (see
the code my 1st post), the receive buffer had already some bytes left over
from previous replies.

So, as mentioned earlier, I do not get the "unknown protocol" error anymore,
however, ssl_connect still fails but this time it does not print out any
error, it simply prints out the following:

///////////////creating TLS Session/////////////////////
SSL_connect failed

I'm trying to connect to smtp.gmail.com:587

Any help will be appreciated.



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