Caddy

Local TLS Trust on Ubuntu 26.04: Caddy, Python, and Chrome in a Sovereign Dev Stack

May 04, 2026

Local TLS Trust on Ubuntu 26.04: Caddy, Python, and Chrome in a Sovereign Dev Stack

A practical record of the problems we encountered establishing local TLS trust across two Ubuntu machines running Caddy, Python, and Chrome — and what is required to fix each layer correctly.