No, you’re not alone. I have automated my LetsEncrypt (DNS auth method) but even though I have the certificate being renewed, it still isn’t picked up by HA.
I even added these lines at the end of the LetsEncrypt renewal cleanup script:
systemctl stop home-assistant
sleep 10
systemctl start home-assistant
Interestingly, if the above command is run once by certbot, HA doesn’t recognise the updated certificate. But if I SSH in after the renewal and run the exact commands again, HA picks it up.
I’m going to keep working on this. I’m going to try a scripted host reboot next, but that’s not my preferred outcome.