The issue concerns relayd with ssl. I've followed the man by the
letter in configuring this and I still come up with the same error
message. I'm trying to loadbalance and proxy ssl connections to non
ssl servers something like this :

HTTPS CLIENT <==> RELAYD SSL REVERSE PROXY :443 <---> NON-SSL WEB SERVER :80

A fairly simple setup that I tested with "pound", another reverse
proxy with ssl capabilities, that worked like charm.

With relayd, I've generated a certificate with GoDaddy, I have the
certificates in the directories the man page mentions, the private key
/etc/ssl/private/192.168.172.77.key and the certificate in
/etc/ssl/192.168.172.77.key where the ip is the frontal relay ip
configured in relayd.conf.

The problem occurs when trying to initiate the SSL handshake, relayd has a hard time generating the random number and recieves a weird error :

SSL library error: httpproxy: relay_ssl_accept: error:140B512D:SSL routines:SSL_GET_NEW_SESSION:ssl session id callback failed relay httpproxy, session 1 (1 active), 0, 192.168.180.253 -> :80, SSL accept error

I tried the exacte same configuration (copy/paste) on an OpenBSD box and the SSL handshake works just fine.

Fix: 

I really don't know.
How-To-Repeat: I've configured pf with the following 2 directives with nothing else
in the file just like what the man page suggests:

rdr-anchor "relayd/*"
anchor "relayd/*"

I've configured relayd with the following directives :

relayd_addr="192.168.172.77"
relayd_port="443"
web_port="80"
table <web_hosts> { 192.168.190.53  }
interval 10
timeout 200
prefork 5

http protocol "httpfilter" {
 return error
 header append "$REMOTE_ADDR" to "X-Forwarded-For"
 header append "$SERVER_ADDR:$SERVER_PORT" to "X-Forwarded-By"
 header change "Keep-Alive" to "$TIMEOUT"
 header change "Connection" to "close"
 response header change "Server" to "Server1"
 ssl { sslv3, tlsv1, ciphers "HIGH:!ADH", no sslv2 ]
}

relay httpproxy {
 listen on $relayd_addr port $relayd_port ssl
 protocol "httpfilter"
 forward to <web_hosts> port $web_port mode loadbalance check icmp
}

Now when I remove the ssl directive from the protocol specs
"httpfilter" and from the "listen" directive within the "relay"
section I forward to my webserver just like a charm. But when I use
the configuration as specified above I get this error when I try to
connect to "https://192.168.172.77":

SSL library error: httpproxy: relay_ssl_accept: error:140B512D:SSL
routines:SSL_GET_NEW_SESSION:ssl session id callback failed
relay httpproxy, session 1 (1 active), 0, 192.168.180.253 -> :80, SSL
accept error

Now when I researched this error it referred to being and error with
the random number generation so I double checked the rights on
/dev/random and /dev/urandom and both were ok (/dev/urandom being a
symlink to /dev/random). I even sued as _relayd user and tested if I
could generate random number and I could :

[_relayd@myserver /etc/ssl]$ od -D -A n /dev/random | head -2
            2530374051      2874409472      1650458018      3736200264
            1776311775       448067355      3385764049       245858356