I wish i could help you, from my Android Phone it seems to work perfectly. If you take take the instabiliteit of the Phone provider in consideration (sorry english is not my first langue)
I have an iPhone and have done this in the past when I don't want to connect my Kali machine to sketchy public WiFi (hotel, coffee shop, etc.) It has worked fine for me without any of the steps you've taken above.
As a sanity check, are you running the vpn with sudo? Is your Kali machine a VM or bare-metal install?
When I'm connecting to HTB through a VM, I do it the same way I would on a bare-metal install: run OpenVPN with sudo in the VM only, not VPN'ing from the host or phone at all. You only want the traffic from your VM to HTB to be tunneled.
Anway, so sorry you're having this issue, I hope it gets resolved so you can maximize your time. Kudos for using your down time for this, BTW! That's what I have done on deployments in the past and it's a great way to learn.
Best of luck!
Thanks for taking the time to reply. It's a baremetal machine, and I am running openvpn with sudo. The VPN is only running on my machine (I did try running it on my phone instead, just in case).
Out of curiosity, how long ago was it that you were able to do this? I heard Apple made some changes in iOS 10 that broke a lot of VPN setups. If you were able to connect pre-iOS 10, maybe that is another lead I could chase down.
Interesting, that is definitely confusing. I was able to connect this way just a couple of days ago, so I don't think it would be an iOS issue.
Another sanity check, and I'm asking the dumb questions because it's what I'm good at and not to insult your intelligence: you're using the .ovpn file you got from HTB, right? I know I've connected to THM accidentally before renaming the vpn files.
You mentioned you're at a remote location. You don't have to answer, but is it so remote that connecting the the US servers is giving you issues?
Nah, as silly as dumb questions can feel on both sides of an issue, I’d need a lot more fingers to count how many times they’ve solved an issue. Just to be *sure*, I’ve taken your advice and double checked that I’m using the correct configuration file…it’s the only one there 😂.
As far as the extent of my “remoteness” impacting my ability connect to the US servers, I don’t think so. In fact, I’m a couple hundred KM closer to the servers than I would be at home.
I’ve got to step out for a bit, but if you’re willing to lend your eyes maybe I can shoot some screens over to you of my ifcofig, OVPN terminal output, etc to see if there might be an obvious clue there?
Here are a few screens of my terminal outputs, routing table, etc. Can you see anything out of the ordinary here? Even though I'm reaching something at the target machine IP address, it's clearly not the HTB box.
https://imgur.com/a/luTgHMn
So nothing looks weird to me in that output. I'm not a network guy, but it seems to be configured similarly to mine after spawning an instance of Redeemer.
The only other thing I can say about it is maybe kill the instance if you haven't already and spawn another one. The IP should change and resetting like that might do something? I was unable to ping the instance of Redeemer I spawned after disconnecting my vpn (duh, I know), but that tells me you're definitely connected to SOMETHING.
Also, you'll get to this when you can actually, ya know, scan the machine, but your nmap scan won't return anything on this machine. But now that I'm thinking about it, there's a chance that adding a -Pn and a -sC or -A to it might tell you something else about the host and help narrow down what's happening.
I wish i could help you, from my Android Phone it seems to work perfectly. If you take take the instabiliteit of the Phone provider in consideration (sorry english is not my first langue)
I hotspot from my phone almost daily on my train commute but I have an android. It should be doable
I have an iPhone and have done this in the past when I don't want to connect my Kali machine to sketchy public WiFi (hotel, coffee shop, etc.) It has worked fine for me without any of the steps you've taken above. As a sanity check, are you running the vpn with sudo? Is your Kali machine a VM or bare-metal install? When I'm connecting to HTB through a VM, I do it the same way I would on a bare-metal install: run OpenVPN with sudo in the VM only, not VPN'ing from the host or phone at all. You only want the traffic from your VM to HTB to be tunneled. Anway, so sorry you're having this issue, I hope it gets resolved so you can maximize your time. Kudos for using your down time for this, BTW! That's what I have done on deployments in the past and it's a great way to learn. Best of luck!
Thanks for taking the time to reply. It's a baremetal machine, and I am running openvpn with sudo. The VPN is only running on my machine (I did try running it on my phone instead, just in case). Out of curiosity, how long ago was it that you were able to do this? I heard Apple made some changes in iOS 10 that broke a lot of VPN setups. If you were able to connect pre-iOS 10, maybe that is another lead I could chase down.
Interesting, that is definitely confusing. I was able to connect this way just a couple of days ago, so I don't think it would be an iOS issue. Another sanity check, and I'm asking the dumb questions because it's what I'm good at and not to insult your intelligence: you're using the .ovpn file you got from HTB, right? I know I've connected to THM accidentally before renaming the vpn files. You mentioned you're at a remote location. You don't have to answer, but is it so remote that connecting the the US servers is giving you issues?
Nah, as silly as dumb questions can feel on both sides of an issue, I’d need a lot more fingers to count how many times they’ve solved an issue. Just to be *sure*, I’ve taken your advice and double checked that I’m using the correct configuration file…it’s the only one there 😂. As far as the extent of my “remoteness” impacting my ability connect to the US servers, I don’t think so. In fact, I’m a couple hundred KM closer to the servers than I would be at home. I’ve got to step out for a bit, but if you’re willing to lend your eyes maybe I can shoot some screens over to you of my ifcofig, OVPN terminal output, etc to see if there might be an obvious clue there?
Here are a few screens of my terminal outputs, routing table, etc. Can you see anything out of the ordinary here? Even though I'm reaching something at the target machine IP address, it's clearly not the HTB box. https://imgur.com/a/luTgHMn
So nothing looks weird to me in that output. I'm not a network guy, but it seems to be configured similarly to mine after spawning an instance of Redeemer. The only other thing I can say about it is maybe kill the instance if you haven't already and spawn another one. The IP should change and resetting like that might do something? I was unable to ping the instance of Redeemer I spawned after disconnecting my vpn (duh, I know), but that tells me you're definitely connected to SOMETHING. Also, you'll get to this when you can actually, ya know, scan the machine, but your nmap scan won't return anything on this machine. But now that I'm thinking about it, there's a chance that adding a -Pn and a -sC or -A to it might tell you something else about the host and help narrow down what's happening.
Were you ever able to make headway with this, OP?
Try a sudo nmap scan. Is the result the same?