Firstly, I appreciate the help/support here. I knew this one seemed strange and it's sort of satisfying to also know I am not crazy 
. Operation not permitted also makes me think I am missing something.
Date/Clock seem good. Accurate and an NTP client as well BTW.
uclient-fetch (http) results:
root@OpenWrt:~# uclient-fetch -4 http://sysupgrade.openwrt.org/json/v1/overview.json
Downloading 'http://sysupgrade.openwrt.org/json/v1/overview.json'
Failed to send request: Operation not permitted
root@OpenWrt:~# uclient-fetch -6 http://sysupgrade.openwrt.org/json/v1/overview.json
Downloading 'http://sysupgrade.openwrt.org/json/v1/overview.json'
Failed to send request: Operation not permitted
Just for tests sake, I also ssh'd into a Pi4 I had sitting in front of the OpenWRT router but obviously still behind my normal AT&T residential gateway and tried wget:
@pi4:~$ wget http://sysupgrade.openwrt.org/json/v1/overview.json
--2025-03-14 09:36:20-- http://sysupgrade.openwrt.org/json/v1/overview.json
Resolving sysupgrade.openwrt.org (sysupgrade.openwrt.org)... 45.140.183.87, 2001:678:6e1:1001:be24:11ff:fe23:4c6d
Connecting to sysupgrade.openwrt.org (sysupgrade.openwrt.org)|45.140.183.87|:80... failed: Connection timed out.
Connecting to sysupgrade.openwrt.org (sysupgrade.openwrt.org)|2001:678:6e1:1001:be24:11ff:fe23:4c6d|:80... failed: Network is unreachable.