No out going mail using PIA VPN with don't pull routes turned off

johnpoz

so your server in your dmz segment, your dmz rules do not allow any email sort of traffic, ie there is no rule there that would allow smtp (tcp 25). Your rule on your dmz segment that would allow traffic is greyed out. that any any rule.

Why are you portforwarding and then natting form wlan segment to your dmz segment?? That makes ZERO sense to me…

If you want your email server to use your PIA vpn connection on your dmz interface that sends your mail traffic through the vpn, which I do not see.

Why don't you explain what you want to happen, and then we can go over the rules that should be setup to allow that. Who do you want your clients in wlan to talk to for mail? Your box in the dmz? Why would think that is a port forward?

kiekar

so your server in your dmz segment, your dmz rules do not allow any email sort of traffic, ie there is no rule there that would allow smtp (tcp 25). Your rule on your dmz segment that would allow traffic is greyed out. that any any rule.

I was always able to receive mail and send out mail without a rule setup on my DMZ interface before configuring PIA and up to now I could send mail out and receive mail. May be my setup is not ideal but it works based on tutorials I found when initially setting up pfSense. I'm using Virtual IPs, 1:1 mappings, and port forwarding to route mail inbound and outbound since I have a block of public IPs /29 to private IPs.

Why are you portforwarding and then natting form wlan segment to your dmz segment?? That makes ZERO sense to me…

I believe the rule on my WLAN was auto generated when I created the port forwarding rule. If I disable the WLAN rule my mail client is unable to connect to the mail server to send out mail

If you want your email server to use your PIA vpn connection on your dmz interface that sends your mail traffic through the vpn, which I do not see.

All I want is to be able to send out mail using what ever means without having my WAN IP exposed but having the PIA IP address instead. My initial thread has two attachments showing what I mean.
Below you will find attachments showing my portfowarding, mappings and virtual IPs

Regards,

Virtual_IP.jpg_thumb

1-1_mappings.jpg_thumb

Port_forwarding.jpg_thumb

kiekar

I would like to have closure on my thread so could anyone let me know if what I'm trying to achieve is possible by sending mail outbound with my own mail server and "Don't pull routes" turned off so my IP address is hidden from my internet provider.

Regards,

Derelict

I would be very surprised if PIA did not block outbound TCP/25 (SMTP).

kiekar

I would be very surprised if PIA did not block outbound TCP/25 (SMTP).

They do block outbound SMTP. I had them whitelist my hostname and IP address.

Derelict

You need a policy routing rule on DMZ. TCP source mail_server_addr port any Dest any port 25 with the gateway set to the VPN gateway. Just like in viragomann's first reply but setting the VPN as the gateway.

ssh to the mail server and:

telnet smtp.gmail.com 25

What happens?

Also put a policy routing rule exactly the same, except port 80, then from the mail server:

curl ifconfig.io

Do you get your WAN IP or the VPN IP?

If not the VPN post your DMZ rules.

kiekar

I'm not sure how to connect using ssh with putty to my mail server nor the curl ifconfig.io command. After setting a rule for smtp on the DMZ interface I used a utility on hmailserver and ran the diagnostic which resulted in not able to connect to a host. I have attached a file showing this and the rule I setup.

Regards,

hmailserver_diagnostic.jpg_thumb

dmz_rules.jpg_thumb

Derelict

Looks to me like PIA is really not allowing you to connect out port 25. You will have to run a packet capture on the PIA interface and run your test again. You will probably see TCP SYN packets outbound to PIA and nothing in reply.

kiekar

I ran the capture packet from pfSense and as you said it looks like packets went outbound but nothing in reply. This of coarse was with "Don't Pull Routes" turned off.
I also tried with "Don't Pull Routes" turned on and of coarse the results were different.
Is this issue resolve able? or do I have to live with the fact that if I use "Don't Pull routes" turned on I will be able to send out mail but my WAN IP will be displayed.

packet_capture.jpg_thumb

packet_capture_dont_pull_roots_on.jpg_thumb

Derelict

That makes zero sense at all. The packet is either routed out the correct interface or it is not. Whether it is a 0.0.0.0/0 route or a policy route just does not matter and has zero impact on whether replies are received. You are looking at something incorrectly.

johnpoz

Im with derelict here I doubt pia allows sending email on 25.. And lets say they did - how would that work since your PTR is not going to match..

Are you trying to send spam? Sending email needs to come from your valid IP that matches both forward and ptr or many players will just block you anyway. I doubt anyone would accept email from a vpn ip anyway..

kiekar

Thanks fellows for your help up to now, but I need to know if it's possible to achieve my goal. I'm far from being an expert on configuring firewalls or networking. If it's possible then let m know what I need to do. I was told in the past that it was possible.

johnpoz

yes it possible to route whatever traffic you want over a vpn connection. But here is the thing that vpn connect needs to allow the traffic you want to send. I would not be surprised if PIA prevents 25 traffic. They are in the business of hiding peoples connections from their isp, being used for geographic circumvention, etc.

Who would route email out through that connection?? Even if they allow it most of the major players would block that.. Simple enough to test, route your traffic over your vpn and see if you can make a connection to some smtp server.

Lets say they do allow it, and where your sending the email doesn't block the vpn IP from sending mail to it. What is your information on your email server. So lets say its mail.domain.tld that resolves to what IP? lets say 1.2.3.4, it sure doesn't resolve to the vpn IP does it lets say 5.6.7.8

Lets say you do all of this, lets say your forward name resolves to the vpn IP, and email comes through there at 5.6.7.8 down the tunnel to your email server. Does the vpn company allow you to modify the ptr on this 5.6.7.8 to say mail.domain.tld - I highly doubt that!! For starters those IPs are shared with all their other customers trying to circumvent geo locations and get netflix from the US for example..

Email really needs to be sent from YOUR actual IP, this IP should be static so not some home isp connection. And you also need to setup the PTR so whatever that IP is resolves to what your mail server says its name is, etc..

You really need to read the RFCs on running a mail server…

kiekar

I was able to finally resolve my issue. After trying to use telnet, ping and tracert commands with no success I finally figured out that I was missing the outbound PIAVPN interface NAT rule for my DMZ source IP range. Even though this did not help to send out mail outbound from my mail server, I was able to use the commands to figure out what worked. Finally I used the mail forwarder in hmailserver to a out.myprovider.com 1025 server from my ISP. Now I happy to say I can send out mail with "don't pull routes" deselected.