I believe restarting Home Assistant is breaking my reverse proxy

Last week I was trying to create a template entity and had to restart HA to get it to load the config file changes. This was probably the third time in that afternoon I had done it and this time I lost connection to my server. I have HA running on a subdomain, along with a few other unrelated services. All of my subdomains and my domain were inaccessible. The browser just says that it can’t find the page. After spending almost an entire week back and forth with Synology support about the issue, I realized I should have tried rebooting the server. That worked and I have been up and running again for about 23 hours. But today I started the upgrade on HA and after it restarted itself I lost connection again.

To clarify, I’m running Home Assistant on a virtual machine on a Synology NAS. I have my domain routed through DDNS to the server, and it is handling the reverse proxy settings through DSM instead of any third party service.

Last time I was able to access HA from within the local network just fine, but until I get home tonight I won’t know if that’s still the case. Though I suspect it will be.

I don’t know how restarting HA (from within, not via the virtual machine) could cause it to break like this but so far it’s 2 for 2 causing it. Or some really strange timing with whatever the actual culprit is.

Does anyone have any suggestions on what this might be caused by, or need additional details I missed?