Cannot initiate HTTPS connection from any type of VPN

departy · Mar 22, 2022, 10:27 AM

Hello, I hope I am in correct section!

Recently I upgraded my PfSense Firewalls to newest CE version.

I discovered that all Web Services with HTTPS do not work. If traffic is FTP, SMB, ICMP, NFS and even HTTP there is no problem. If HTTPS I get all states become with CLOSED:SYN_SENT status

Local Sites can access their Web Servers with HTTPS(10.0.0.100 -> 10.0.0.5), but the remote site cannot(10.0.0.100 -> 10.10.0.5).
Somewhere I read that it could be because of asymmetric routing, but I dont feel that's the case.

Rules on remote site

They are exactly same on local sight respective to the firewall
Same issue is valid for Any type of VPN -> OpenVPN, WireGuard, IPSec

Any ideas would be much appreciated! Please HELP ;(

johnpoz · Mar 22, 2022, 4:22 PM

@departy if it was asymmetrical none of the protocols would work.

So those look like your lan site.. What are the openvpn rules on both sites. What is your tunnel network being used?

If your saying other protocols work - validate your vpn interface rules allow for 443. Also don't forget a host firewall.. Maybe this 10.10.0.x address firewall doesn't allow the remote 10.0.0 network..

departy · Mar 22, 2022, 4:22 PM

@johnpoz

No rules regarding port 443 so far.

"Also don't forget a host firewall.. Maybe this 10.10.0.x address firewall doesn't allow the remote 10.0.0 network.."

How and where would I check that?

johnpoz · Mar 22, 2022, 4:33 PM

Both sides?

johnpoz · Mar 22, 2022, 4:54 PM

@departy said in Cannot initiate HTTPS connection from any type of VPN:

How and where would I check that?

In the server your hosting the https site on.

simple test, sniff on pfsense (packet capture under diag menu).. On the interface to your https box is connected too - when you try and access it from the other site - do you see the pfsense sending the traffic to the server.. If so but no answer - that screams firewall... If you don't see it move up the line towards where your sending the traffic to make sure its getting to pfsense.

So you see the traffic on the vpn interface? If not do you see it on the other end going out the vpn interface? Maybe the other end is using policy routing?

departy · Mar 22, 2022, 4:56 PM

@johnpoz
OpenVPN is from Laptop to 'Remote Site' -> 443 isnt working
OpenVPN to 'Local Site' -> 443 is working

Something is wrong on the remote site. They allow ALL I have * to * rules
VPN -> LAN - Allow all

I continue see (States Remote site)

NAT Remote

VPN Rules:

OpenVPN, WireGuard, IPSec to -> 10.10.0.4:443 not working (example, no ip:443 works).

departy · Mar 22, 2022, 5:00 PM

@johnpoz
Package Capture to 10.10.0.4 on VPN interface

Package Capture to 10.10.0.4 on LAN interface

johnpoz · Mar 22, 2022, 5:02 PM

@departy said in Cannot initiate HTTPS connection from any type of VPN:

Package Capture to 10.10.0.4 on LAN interface

So you can see pfsense is sending on the traffic to the 10.10.0.4 address, but no response. So you need to look to 10.10.0.4 why its not answering.. Wrong gateway? (not pfsense) firewall? Wrong mask and it thinks 10/8 is local so it never sends the traffic back to pfsense, etc.

departy · Mar 22, 2022, 5:09 PM

@johnpoz
But then, why when I am at the 'Remote Site' and with IP on LAN address I can successfully open 10.10.0.4:443 ?

Edit: AAAAAAAAHhhhh I see your point. I now have a lead... Will chase on it and ping again if need additional brain to resolve this nonsense Thank you!

Edit2: Thank you for your time!

departy · Mar 23, 2022, 11:30 AM

@johnpoz I currently cannot get physically on remote site and have a though.

Can you tell me what happens if 10.10.0.4 has a static IP address Set on the client itself not on PfSense side.
Is it possible the problem to be related to that? Since PfSense is virtualized, 0.4 is the ESXi, I have set a static IP address in case PfSense dies for some reason to have a way on the other side to turn it on from the network.

Also for some reason I lost Ping and other services today to that server. Troubleshooting it now

johnpoz · Mar 23, 2022, 11:43 AM

@departy said in Cannot initiate HTTPS connection from any type of VPN:

Can you tell me what happens if 10.10.0.4 has a static IP address Set on the client itself not on PfSense side.

How a client gets an IP be it dhcp or static on the device makes no difference.. IP address is IP address. As long as set correctly, correct mask, correct gateway.

0.4 is the ESXi

Huh?? While sure your esxi host would have an IP in whatever network your using.. That wouldn't be the same IP as some VM your trying to access. Unless your were natting on esxi, which I don't think you even can.. Is this vmware workstation and not esxi?

So your trying to access the webgui of esxi?

departy · Mar 23, 2022, 1:14 PM

@johnpoz
Yes, I am trying to access WebUI of ESXi> I am pretty much sure I have default settings on firewall and etc. It used to work until pfsense upgrade.

johnpoz · Mar 23, 2022, 1:14 PM

@departy it never going to work if you don't get an answer... You can see the traffic is sent to the IP.. Is that the correct mac address..

Pfsense has nothing to do with answers not being returned... Sniff on your esxi host - is it seeing the traffic? You posted your sniffs and traffic is being sent on to that IP to 443 from pfsense.

departy · Mar 23, 2022, 2:00 PM

@johnpoz Okay I feel stupid right now, but tbh I would have never gotten to the answer without you!

Noticed the wrong gateway which somehow got auto assigned. I am new to the settings I am applying and assumed some stuff happens automatically. Now I made the necessary changes and fixed the gateway and made sure it wont happen again.

Thank you soo much for wasting your time with my issue! But I gained some additional knowledge on how to troubleshoot future issues like this. Thank you!

johnpoz · Mar 23, 2022, 2:05 PM

@departy glad I could help - anything that gets to the answer is not really a waste of time.

Could of prob figured that out sooner, other than you saying other protocols worked... They sure wouldn't of worked to this box, if his gateway was not correct.

departy · Mar 23, 2022, 3:48 PM

@johnpoz I recently moved my pfsense box to VM on an ESXi. Have a learning curve to that. I set some prevention methods in case PfSense died, I could reach it via static IPs. Used to work, but after the upgrade to 2.6 something must have happened and trigger it this change in gateway. Lost my head for few days wondering what and where went wrong

Now question is why LAN (10.10.0.1) could have established connection with 192. I will dwell on that next few days.

johnpoz · Mar 23, 2022, 4:12 PM

@departy said in Cannot initiate HTTPS connection from any type of VPN:

Now question is why LAN (10.10.0.1) could have established connection with 192.

What was talking to what - from your routing table your have 3 different networks there attached to your esxi host. Are you overlapping those IPs on the same L2? Do you have multi homed devices (interfaces in more than 1 network)?

vmk - those are you vmkernal networks? Why would you have more than 1? I could see putting different vms on a different network. But have never setup esxi with vmkern in more than 1 network.. Multi homing devices is almost always a bad idea ;) Can lead to asymmetrical traffic flow is normally the problem.

If you have a completely isolated san that is different..

My nas and pc are multi homed, but only in the sense that they have an isolated network that they can talk to each other at 2.5ge for file movement, a san if you will.