So after searching deep into different posts I found one obscurely related. Apparently my system was attempting to use IPV6 for some DNS requests and eventually it would time out.

I had to add the following line to my /etc/squid/squid.conf

dns_v4_first on

As it implies, It forces the system to use IPV4 exclusively.

I wish there was more information I could post that would allow people to find this easier, But then again by the lack responses it sounds like not to many people have had this issue.

1447709394.956 22 192.168.1.168 TCP_REFRESH_UNMODIFIED/304 284 GET http://www.avagotech.com/cs/Satellite? - HIER_DIRECT/68.142.79.70 image/jpeg
1447709394.956 22 192.168.1.168 TCP_REFRESH_UNMODIFIED/304 284 GET http://www.avagotech.com/cs/Satellite? - HIER_DIRECT/68.142.79.70 image/jpeg
1447709394.963 28 192.168.1.168 TCP_REFRESH_UNMODIFIED/304 283 GET http://www.avagotech.com/cs/Satellite? - HIER_DIRECT/68.142.79.70 image/jpeg
1447709394.971 18 192.168.1.168 TCP_REFRESH_UNMODIFIED/304 282 GET http://www.avagotech.com/cs/Satellite? - HIER_DIRECT/68.142.79.70 image/jpeg
1447709394.980 19 192.168.1.168 TCP_REFRESH_UNMODIFIED/304 284 GET http://www.avagotech.com/cs/Satellite? - HIER_DIRECT/68.142.79.70 image/jpeg
1447709394.981 20 192.168.1.168 TCP_REFRESH_UNMODIFIED/304 284 GET http://www.avagotech.com/cs/Satellite? - HIER_DIRECT/68.142.79.70 image/jpeg
1447709394.985 18 192.168.1.168 TCP_REFRESH_UNMODIFIED/304 284 GET http://www.avagotech.com/cs/Satellite? - HIER_DIRECT/68.142.79.70 image/jpeg
1447709394.993 112 192.168.1.168 TCP_REFRESH_MODIFIED/200 30769 GET http://www.avagotech.com/cs/Satellite? - HIER_DIRECT/68.142.79.70 image/jpeg
1447709394.995 112 192.168.1.168 TCP_REFRESH_MODIFIED/200 29156 GET http://www.avagotech.com/cs/Satellite? - HIER_DIRECT/68.142.79.70 image/jpeg
1447709395.371 63 192.168.1.168 TCP_MISS/404 586 GET http://www.avagotech.com/avg_static/css/img/transparent.png - HIER_DIRECT/68.142.79.70 text/html
1447709395.598 172 192.168.1.168 TCP_MISS/302 673 GET http://video.limelight.com/player/embed.js - HIER_DIRECT/69.164.39.228 text/html
1447709422.403 59830 192.168.1.168 TCP_MISS/304 305 GET http://img2.blogblog.com/img/icon18_edit_allbkg.gif - HIER_DIRECT/216.58.217.201 -
1447709422.407 59834 192.168.1.168 TCP_MISS/304 305 GET http://www.blogger.com/img/icon_delete13.gif - HIER_DIRECT/216.58.216.41 -
1447709422.409 60016 192.168.1.168 TCP_MISS/200 653 GET http://img1.blogblog.com/img/icon18_email.gif - HIER_DIRECT/216.58.219.9 image/gif

This was just a site in my bookmarks. TCP_REFRESH all came up nice a speedy. TCP_MISS all took 30-60 seconds to finish. Almost like when Squid actually reaches out for content.
This log file was taken off a fresh RE-boot thinking maybe something wasn't jiving in memory.

Hopefully someone has some idea's. I just found an additional piece of information. It only runs slow on HTTPS sites. Unsecured sites come up full speed!

Squid running REALLY slow

So I installed ClearOS 7.0, Been a fan of ClearOS and its predecessors all the way back to ClarkConnect.

Im using WebProxy (Squid) and im running into a unique issue I haven't had with Squid. When visiting a website I have not gone to before with WebProxy enabled it takes anywhere to 30-60 seconds for the Website to come up. If I Visit a Site that have been to before with the WebProxy on the site comes up quite fast.

If I disable WebProxy all sites come up with no issues.

I've tried a few suggestions on ClearOS's site with no change in performance.

Anyone out there have some ideas I can try to troubleshoot the issue down to its problem?

Yup, As I read your reply it dawned on me that has to be what it is. I added the Static route but broke the remote box network IF at the same time. So I have to wait till the device is back in my hands.

Thanks for the info!

VPN not working both ways

Setup OpenVPN both sides using instructions on ClearOS site.

I get connection, And can ping OpenVPN devices. Can ping all devices on direction. But one direction I can only ping the OpenVPN device.

Server ClearOS 6 (IP: 192.168.1.1)

dev tun
port 1195
ifconfig 10.8.222.40 10.8.222.41
route 192.168.2.0 255.255.255.0
comp-lzo
keepalive 10 60
persist-key
persist-tun
user nobody
group nobody
secret static.key

Can ping from 192.168.1.1 to 192.168.2.4 but not other devices in 192.168.2.*

Remote Ubuntu Desktop (IP:192.168.2.4)

dev tun
port 1195
remote my.domain.name 1195
ifconfig 10.8.222.41 10.8.222.40
route 192.168.1.0 255.255.255.0
comp-lzo
keepalive 10 60
persist-key
persist-tun
user nobody
group nobody
secret static.key

I can ping ALL devices on the 192.168.1.1 network.

I have to run a device on the remote side on IP 192.168.2.4 due to the unique network setup there. Not sure if im just missing something because of the specific IP or something complete on one side that allows the send/return ping?

Anyone have any ideas?