We also run corporate web filtering which inspects SSL, and have had the similar issue with Android Studio and Gradle.
Adding our Webfiltering root CA certificate to Android Studio resolved all cert errors except for Gradle, we even tried ticking the ‘accept non-trusted certificates automatically’ but still had issues with Gradle?
In an attempt to resolve it I disabled SSL inspection for https://services.gradle.org/ (location of what studio wanted to access) but this didn’t resolve the issue. After much messing around I spotted that https://services.gradle.org/ certificate is actually issued to ssl473435.cloudflaressl.com rather than itself? Not sure how this passes validation in browser but it does. Anyhow adding this as an SSL inspection exception resolved the issue for us. I don’t know if this is something gradle can change to reduce issues with cooperate entities & improved support for Android Studio’s settings.
Note to others who dont have corperate firewall, you may have a desktop firewall that does need similar exceptions adding.
I’ve logged a support call with Android Studio support as well to see if there is something they can do to provide better support for this.