From the access.log. I tried to select, clean up and edit IP addresses etc. (in italics) to the best of my abilities. Note that I when I changed to the bad server, I really got that line five times.
Bootup, good server
127.0.0.1 NONE/200 0 CONNECT
www.tunnelblick.net:443 - HIER_NONE/- -
127.0.0.1 TCP_MISS/200 839 GET
https://www.tunnelblick.net/ipinfo - HIER_DIRECT/
11.22.33.44 text/plain
iTunes, update podcast
127.0.0.1 NONE/200 0 CONNECT
podcast_server.net:443 - HIER_NONE/
127.0.0.1 TCP_MISS/200 21009 GET
podcast_URL.xml - HIER_DIRECT/
55.66.77.88 application/xml
Email image
127.0.0.1 NONE/200 0 CONNECT
www.website.com:443 - HIER_NONE/- -
127.0.0.1 TCP_MISS/200 16926 GET
? - HIER_DIRECT/
99.10.11.12 image/jpeg
127.0.0.1 TCP_MISS/200 4393 GET
https://emailsignature.trustpilot.com/xyz.png - HIER_DIRECT/
100.110.120.130 image/png
Change to bad server
127.0.0.1 NONE/200 0 CONNECT
www.tunnelblick.net:443 - HIER_NONE/- -
127.0.0.1 NONE/200 0 CONNECT
www.tunnelblick.net:443 - HIER_NONE/- -
127.0.0.1 NONE/200 0 CONNECT
www.tunnelblick.net:443 - HIER_NONE/- -
127.0.0.1 NONE/200 0 CONNECT
www.tunnelblick.net:443 - HIER_NONE/- -
127.0.0.1 NONE/200 0 CONNECT
www.tunnelblick.net:443 - HIER_NONE/- -
iTunes, update podcast
127.0.0.1 NONE/200 0 CONNECT
podcast_server.net:443 - HIER_NONE/- -
127.0.0.1 TCP_MISS/503 388 GET
podcast_URL.xml - HIER_NONE/- text/html
Email image
127.0.0.1 NONE/200 0 CONNECT
www.website.com:443 - HIER_NONE/- -
127.0.0.1 TCP_MISS/503 388 GET GET
? - HIER_NONE/- text/html
127.0.0.1 TCP_MISS_ABORTED/000 0 GET
https://emailsignature.trustpilot.com/xyz.png - HIER_NONE/- -
Question is then, why those 503's instead of 200's?
From the cache.log. Maybe less useful, but who am I to judge...
Bootup, good server
5 times: [date / time] kid1| WARNING: no_suid: setuid(0): (1) Operation not permitted
Then about 80 lines similar to:
[date / time] kid1| WARNING: failed to find or read error text file ERR_DIR_LISTING
[date / time] kid1| ERROR: loading file '/Library/Squid/errors/templates/ERR_SHUTTING_DOWN': (2) No such file or directory
[date / time] kid1| WARNING: failed to find or read error text file ERR_SHUTTING_DOWN
[date / time] kid1| ERROR: loading file '/Library/Squid/errors/templates/ERR_PROTOCOL_UNKNOWN': (2) No such file or directory
[date / time] kid1| WARNING: failed to find or read error text file ERR_PROTOCOL_UNKNOWN
Following email access:
[date / time] kid1| Error parsing SSL Server Hello Message on FD 35
Bad server
Following new email access, came right after to the line above.
[date / time] kid1| ERROR: loading file '/Library/Squid/errors/en-us/ERR_DNS_FAIL': (2) No such file or directory
[date / time] kid1| WARNING: Error Pages Missing Language: en-us
[date / time] kid1| ERROR: loading file '/Library/Squid/errors/en-us/ERR_DNS_FAIL': (2) No such file or directory
[date / time] kid1| WARNING: Error Pages Missing Language: en-us
If something's not clear, just ask, I'm keeping the complete logs at their different stages.