Can you ping server 1 from the subnet router?
Make sure to check if you have a firewall blocking ICMP packets on server 1 or somewhere between.
Maybe run traceroute from both serves and compare the route taken and where it stops.

Sadly we lost that fight to the other centralised platform in Bluesky

Yes, but that’s what you would need to do and get if everyone had to install an intermediate cert.

Not really, because the client system is configured to go through the proxy. That proxy will connect to the website and do filtering on the unencrypted content because it is initiating the connection. Next it’ll re-encrypt everything with its own certificate and serve it to the client.

From having worked in an enterprise environment, there’s a chunk of websites that break when you intercept their SSL connection.

Nextcloud News with the accompanying app on my phone. I was lazy that day

Interesting. I somehow rewired my brain when I switched to Linux and now I’m constantly annoyed when middle click doesn’t paste.

You need a calendar and time handling anyways for logging purposes and to set timers correctly. It’s likely not that much extra work exposing that functionality.

Arch