Trouble thering with iPhone

[jackthetripperr]

I’m working out in a remote location and find myself with a lot of time on my hands. To put my time to good use, I decided to take up some courses on Hack the Box. For those who don't know, HTB provides training in IT security. One of the features the website has is the ability to connect directly to one of their machines via VPN. The machines are deliberately misconfigured so you can practice various offensive security tactics. Unfortunately, I am having trouble connecting to HTB boxes on Kali Linux through OVPN.

On HTB, you need to be connected their network via the OVPN configuration they have you download. Once your connection is registered, you can "spawn" one of the machines, at which point you'll be given it's IP address and you can begin enumeration. On my home internet, everything works without issue. When I connect to the internet by tethering my phone, nothing works properly. I can connect to the VPN, my connection is seen by HTB and I can spawn a machine, but I ran into trouble as soon as I start enumerating machines.

When I scan the given IP address with nmap, a whole whack of random ports and services are returned. It is very clear that the machine I am scanning is not the HTB one. For reference, I’m am currently trying to do the Redeemer machine. Here are some trouble shooting steps I’ve taken so far:

-Triple checked that I am scanning the correct IP address

-Tried both UDP and TCP configurations with OVPN

-Made the connection to OVPN directly on my Kali machine and directly on my phone via the OVPN Connect app (separately, of course)

-Disabled iCloud private relay

-Enabled the “maximize compatibility” in the tethering settings of my iPhone

-Ensured I am only running a single OVPN process in Kali

I am at a loss. Has anyone faced this issue before, and if so, were you able to find a solution? I’d really appreciate any suggestions whatsoever. Thanks!

PS:I've posted this in various communities that might be more appropriate for this topic but I am having serious trouble finding an explanation let alone a solution, so I figured I'd see if anyone here might be able to help me pinpoint the issue if it happens to related to my VPN setup.

TLDR: While tethering with my iPhone, it doesn't seem like I am actually connected to my VPN.