Hi, I already posted this but no one responded - I’m guessing that I posted too much of my config file and too much of my log. Now, I just included what is important to fix the problem and if you want complete files posted I can. I recently configured Squid to ssl-bump connections and dynamically generate certificates. I am running Squid 3.3.3 on Ubuntu 13.10. ————————————————————————————— ssl_bump server-first #Devices configured to use the proxy. No interception for HTTPS http_port 3128 https_port 3128 cert=/usr/ssl/myCA.pem #Devices configured to use the proxy. Interception for HTTPS http_port 3129 ssl-bump generate-host-certificates=on dynamic_cert_mem_cache_size=4MB cert=/usr/ssl/myCA.pem #Devices unconfigured to use the proxy. Sent by the router. http_port 3127 intercept ssl-bump cert=/usr/ssl/myCA.pem https_port 3126 intercept ssl-bump cert=/usr/ssl/myCA.pem ————————————————————————————— Squid worked flawlessly until I added the http_port 3129 line with the ssl-bump and generate host certificates. After this, Squid now crashes anywhere from 1 - 12 hours. Here is part of my cache.log file ————————————————————————————— 2014/04/12 21:40:37 kid1| Accepting HTTP Socket connections at local=[::]:3128 remote=[::] FD 11 flags=9 2014/04/12 21:40:37 kid1| Accepting SSL bumped HTTP Socket connections at local=[::]:3129 remote=[::] FD 12 flags=9 2014/04/12 21:40:37 kid1| Accepting NAT intercepted SSL bumped HTTP Socket connections at local=0.0.0.0:3127 remote=[::] FD 13 flags=41 2014/04/12 21:40:37 kid1| Accepting HTTPS Socket connections at local=[::]:3128 remote=[::] FD 14 flags=9 2014/04/12 21:40:37 kid1| Accepting NAT intercepted SSL bumped HTTPS Socket connections at local=0.0.0.0:3126 remote=[::] FD 15 flags=41 2014/04/12 21:40:37 kid1| ERROR: listen( FD 14, [::] [ job9832], 1024): (98) Address already in use 2014/04/12 21:50:56 kid1| clientNegotiateSSL: Error negotiating SSL connection on FD 30: error:1407609C:SSL routines:SSL23_GET_CLIENT_HELLO:http request (1/-1) ***MESSAGE ABOVE REPEATED MULTIPLE TIMES 2014/04/12 21:56:29 kid1| WARNING: HTTP: Invalid Response: No object data received for https://www.facebook.com/connect/ping ***MESSAGE ABOVE REPEATED MULTIPLE TIMES 2014/04/13 22:08:08 kid1| WARNING! Your cache is running out of filedescriptors ***MESSAGE ABOVE REPEATED MULTIPLE TIMES 2014/04/13 22:13:08 kid1| NF getsockopt(SO_ORIGINAL_DST) failed on local=192.168.0.10:3126 remote=192.168.0.49:39402 FD 62 flags=33: (2) No such file or directory ***MESSAGE ABOVE REPEATED MULTIPLE TIMES 2014/04/13 22:22:14 kid1| WARNING! Your cache is running out of filedescriptors ———————————————————————————————————— I’m thinking it is crashing from the lack of file descriptors. I changed my configuration file to give it 4096 file descriptors and the cache.log confirms this when starting up. I would really appreciate any ideas that anyone might have to fix this problem. Thanks!