Hosting WebServer Intermittent Communication Issues

  • I have setup a web server vm running on Esxi 6.0. This server listens on 443 and 80 and has a public IP address allotted to it with a 1 to 1 nat. The majority of our clients that connect to it are able to communicate with it without issue on either web page. Some of our clients are not able to communicate with it and eventually receive a timeout error. I can run a capture on the pfsense and see traffic coming and going without issues to the box from the troubled client. If I reboot the web server the troubled clients can connect once and then never again until another reboot.

    I don't feel like this is the pfsense but I am not sure because it seemed to work fine when we had our ASA in use instead of the pfsense.

    I am using manual outbound nat and 2.3.1-RELEASE. I suspect if it is pfsense then it is a setting that is rewriting the return packet to the clients outside.

    Thanks Daniel

  • Do you have additional packets installed like Snort, Suricata or pfBlockerNG?
    If so, deactivate it for troubleshooting.