Firstly, thanks a lot of responding to my post! :D , responses below to the best of my ability.
You are using Local DNS records on Pihole that point to NPM as Reverse proxy to the specific Hosts?
Yes
Do you have proper MASKs configured on all of these devices? /24
Not entirely sure about this, but all the services get their IP's directly from OPNSense on Network: LAB which is on 10.10.200.0/24 Network
Can your PC from which you try to access the domain resolve the domain? do nslookup sw-lab.nerdbit.org
Last login: Mon Sep 2 22:13:36 on ttys000~ % nslookup sw-lab.nerdbit.orgServer: 10.10.100.1 Address: 10.10.100.1#53
** server can't find sw-lab.nerdbit.org: NXDOMAINIs your PC using the DNS that has these local records set?
This PC/Laptop is on LAN network which is on 10.10.100.0/24 Network.
hough not explicity specified, the DNS is 10.10.100.1 (which basically is OPNSense Firewall itself), I do however have adguard running on it, not sure if that will help?
Do you have proper certificates or wildcard certificate on NPM with domains properly set to use these certs?
As I'm navigating my way through this, I simply setup a wildcard .*nerdbit.org SSL and used it for all the services and seems to be working as long as I'm connected to LAB network only. Open to making changes.
I've the domain registered with Cloudfare if that helps.Thanks yet again.
You are using Local DNS records on Pihole that point to NPM as Reverse proxy to the specific Hosts?
Yes
Do you have proper MASKs configured on all of these devices? /24
Not entirely sure about this, but all the services get their IP's directly from OPNSense on Network: LAB which is on 10.10.200.0/24 Network
Can your PC from which you try to access the domain resolve the domain? do nslookup sw-lab.nerdbit.org
Last login: Mon Sep 2 22:13:36 on ttys000~ % nslookup sw-lab.nerdbit.orgServer: 10.10.100.1 Address: 10.10.100.1#53
** server can't find sw-lab.nerdbit.org: NXDOMAINIs your PC using the DNS that has these local records set?
This PC/Laptop is on LAN network which is on 10.10.100.0/24 Network.
hough not explicity specified, the DNS is 10.10.100.1 (which basically is OPNSense Firewall itself), I do however have adguard running on it, not sure if that will help?
Do you have proper certificates or wildcard certificate on NPM with domains properly set to use these certs?
As I'm navigating my way through this, I simply setup a wildcard .*nerdbit.org SSL and used it for all the services and seems to be working as long as I'm connected to LAB network only. Open to making changes.
I've the domain registered with Cloudfare if that helps.Thanks yet again.