Good morning everyone,
I am currently experiencing a configuration anomaly that I am unable to properly interpret.
Recently, I decided to perform a complete upgrade of my home infrastructure. To ensure greater consistency and a cleaner configuration, I opted for a fresh installation of the system, avoiding the restoration of any existing backups. This decision was driven by the need to remove legacy configurations accumulated over time that are no longer necessary, as well as to improve the overall maintainability of the environment.
During the reconfiguration phase, I implemented the URL filtering service, with particular focus on HTTPS traffic inspection. To achieve this, I carefully followed the official documentation available at the following link:
Specifically, I configured the WPAD (Web Proxy Auto-Discovery Protocol) mechanism to allow network clients to automatically detect proxy settings and apply filtering policies, including for encrypted connections.
However, despite strictly following all the steps outlined in the guide (including the configuration of the wpad.dat file, DHCP/DNS options, and proxy parameters), the observed behavior is not as expected: the system does not seem to correctly apply filtering when the configuration is distributed automatically.
To rule out client-side issues, I performed tests by manually configuring the proxy settings within applications. In this scenario, filtering works correctly, including HTTPS traffic handling. This suggests that the issue is likely confined to the auto-discovery process or the configuration distribution mechanism.
At this point, I am unable to precisely identify where the problem might lie (WPAD configuration, DNS resolution, DHCP options, or another component in the chain).
Do you have any suggestions on which components or logs I should analyze to isolate the root cause of the issue?

