@m85 I'm not entirely sure if my suggestion will help but you can try setting up mDNS in Omada, here's a page from the knowledge base:

https://community.tp-link.com/en/business/kb/detail/412610

The reason I suggest this is because:

1. Your OpenVPN IP Pool and LAN pool are two different subnets, mDNS will forward broadcast packets across different subnets for you.

2. You are using an iOS device, they typically rely on the Bonjour service (mDNS) for discovery.

  @itsAlex thanks I will try that. I tried to put the vpn server on the same subnet before. That did not help. I will try with mDNS enabled. 

  @m85 If mDNS doesn't work, you can also try setting the primary DNS server as the gateway IP address in your VPN policy. 

I am not sure if this is done by default in Omada, but you can try this. Your router/gateway should be caching DNS lookups for faster resolves in future requests. The router may also have information about your local clients and their hostnames/IP addresses.

Hypothetically, if OpenVPN used your gateway as a DNS server, then it should be able to resolve local hostnames. If the router/gateway does not have info about a DNS query, the gateway will forward the query to the next DNS server (most likely external, provided by your ISP or a custom one such as 1.1.1.1 (cloudflare) ).

Let me know if this helps.

  @itsAlex mDNS did not help.

As my pihole is my DNS server. I set the IP in the OpenVPN configuration as the primary DNS server. Do you mean this? I also set the IP pool to the same subnet as my network.

I exported the config again and imported it on my iOS device. It still does not work to access domain.local hostnames. Local IP addresses do work.

  @m85 Yes, that is what I meant. However, if you have your Pi-hole as your primary DNS server, try setting the secondary DNS server as your gateway IP address.

Does Pi-hole have the ability to set external DNS servers when it is unable to resolve a query? If so, Try setting one of the external DNS servers as your gateway IP in Pi-hole instead of doing it in Omada, or maybe try doing it in both as an experiment.

Let me know if this helps.

  @itsAlex i set both the primary and secondy DNS in the OpenVPN server to 192.168.1.1 as this is my gateway ip. In both cases it did not solve my problem.

Also i was checking my pihole and was seeing these warning messages. Not sure what they mean. I am not a network export.

  @m85 It might be some setting in my pihole that should make this work. I found these settings. I tried the Permit all origins settings. But it did not help also.

  @m85 i also put DNS in the Omada controller back to auto. So it wont use PiHole anymore. That did not help aswell.