I upgraded my IO::Socket::SSL to the latest version, it took a while since I also had to upgrade a bunch of other stuff to get it to work, but at least now I have all the utilities.

I ran your code to generate a certificate, setup the server and connect to it, that all worked. Next I ran the server on the host which I'm trying to connect to and modified the ip for the client, still worked. Then I configured apache to use that exact certificate and and again it worked!

Convinced that all my troubles were over I tried to execute my script from the original post to see if it would also work with the new certificate but...

DEBUG: .../IO/Socket/SSL.pm:2555: new ctx 34454560
DEBUG: .../IO/Socket/SSL.pm:539: socket not yet connected
DEBUG: .../IO/Socket/SSL.pm:541: socket connected
DEBUG: .../IO/Socket/SSL.pm:563: ssl handshake not started
DEBUG: .../IO/Socket/SSL.pm:599: not using SNI because hostname is unk
+nown
DEBUG: .../IO/Socket/SSL.pm:631: request OCSP stapling
DEBUG: .../IO/Socket/SSL.pm:650: set socket to non-blocking to enforce
+ timeout=180
DEBUG: .../IO/Socket/SSL.pm:663: Net::SSLeay::connect -> -1
DEBUG: .../IO/Socket/SSL.pm:673: ssl handshake in progress
DEBUG: .../IO/Socket/SSL.pm:683: waiting for fd to become ready: SSL w
+ants a read first
DEBUG: .../IO/Socket/SSL.pm:703: socket ready, retrying connect
DEBUG: .../IO/Socket/SSL.pm:2458: did not get stapled OCSP response
DEBUG: .../IO/Socket/SSL.pm:2411: ok=1 cert=34885312
DEBUG: .../IO/Socket/SSL.pm:1559: scheme=www cert=34885312
DEBUG: .../IO/Socket/SSL.pm:1569: identity=192.168.100.222 cn=________
+_____ alt=
DEBUG: .../IO/Socket/SSL.pm:1769: hostname verification failed
DEBUG: .../IO/Socket/SSL.pm:663: Net::SSLeay::connect -> -1
DEBUG: .../IO/Socket/SSL.pm:1780: SSL connect attempt failed

DEBUG: .../IO/Socket/SSL.pm:1785: SSL connect attempt failed error:140
+90086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify fai
+led
DEBUG: .../IO/Socket/SSL.pm:669: fatal SSL error: SSL connect attempt 
+failed error:14090086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certif
+icate verify failed
DEBUG: .../IO/Socket/SSL.pm:1769: IO::Socket::IP configuration failed
DEBUG: .../IO/Socket/SSL.pm:2588: free ctx 34454560 open=34454560
DEBUG: .../IO/Socket/SSL.pm:2593: free ctx 34454560 callback
DEBUG: .../IO/Socket/SSL.pm:2600: OK free ctx 34454560
500 Can't connect to 192.168.100.222:4433 (certificate verify failed)
Content-Type: text/plain
Client-Date: Wed, 07 Jan 2015 23:00:51 GMT
Client-Warning: Internal response

Can't connect to 192.168.100.222:4433 (certificate verify failed)

SSL connect attempt failed error:14090086:SSL routines:SSL3_GET_SERVER
+_CERTIFICATE:certificate verify failed at /usr/local/share/perl/5.14.
+2/LWP/Protocol/http.pm line 49

[download]
On the serverside openssl s_server said: 
Using default temp DH parameters
Using default temp ECDH parameters
ACCEPT
bad gethostbyaddr
ERROR
140707196729000:error:14094416:SSL routines:SSL3_READ_BYTES:sslv3 aler
+t certificate unknown:s3_pkt.c:1256:SSL alert number 46
shutting down SSL
CONNECTION CLOSED
ACCEPT

[download]

trying to connect to apache with the new cert also failed. This leaves me to think that there is something wrong with (the way I'm using) LWP::UserAgent.

Is it possible to handle the ssl connection with IO::Socket::SSL directly but still have all the LWP::UserAgent functionality for my interaction with the server after the connection is established?

In reply to Re^2: HTTPS connection with LWP and self-signed certificate by Anonymous Monk
in thread HTTPS connection with LWP and self-signed certificate by Anonymous Monk

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