ORBI Hair Pinning

[den452001]

I have a server that unable to access external IP Addresses when connected to LAN.

For example External Ip Address: 108.111.111.222
Internal Ip Address. 192.168.1.100

When connected to the same network, Internal IP works, but external IP Won't work. However using the same device server machine , external ip works.

When i'm outside with other networks, External IP Works Flawlessly.

Device: ORBI RBR850 Server: Ubuntu 20.04

[Nnyan]

So I'm not exactly sure if I understand your question, when you say hairpinning do you mean NAT loopback?   Your post doesn't seem to be describing a hairpin situation but that could be my misinterpretation.  Correct me if I'm wrong here:

108.111.111.222  WAN (ISP) port address on RBR850

192.168.1.100   Ubuntu Server

How exactly are you connecting everything in your two different scenarios?  Are you using VLANs ?