Rogers 3G + tethering + PPTP VPN not working

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Rogers 3G + tethering + PPTP VPN not working

Hi all

I've successfully configured my iPhone 3G (with OS 3.0) for tethering, I've had Rogers enable a public IP APN option on my account, I've deployed a custom configuration for the appropriate APN via a custom profile to my iPhone (that one took way too much research to sort out as my ISP was unable to help aside from telling me that "you are not able to change APN settings on an iPhone"). I finally figureed out how to deploy a custom APN setup through the iPhone Configuration Utility 2.0 (yay) and I have all of my VPNs working fine from the iPhone itself, but ... when I tether to my laptop via USB I can connect to L2TP based VPN's without issue, but not PPTP based VPNs.

I have multiple L2PT connections working while tethered via USB to my laptop (initiating VPN connection from my laptop), but for the life of my I can't any PPTP based VPN setups to connect at all. They work fine when I initiate the connection from the iPhone to the PPTP networks over 3G, but when tethered it's a no go (initiating from my laptop).

Am I missing something in my setup or are other users having the same issue? It almost seems like the NAT setup that iPhone OS 3.0 is causing the issue (missing NAT transversal options)? Why L2PT is working and PPTP is not is a mystery.

Any suggestions would be appreciated. I'm trying to get this sorted out in order to advise one of my clients whether or not using tethered iPhones will be an option for their traveling laptop users, but they need to connect to PPTP based VPN's.

MacPro 8core 8G/2TB, PB 17" 1.6ghz, Intel Mini, Dual G5 1.8Ghz, ANS, Mac OS X (10.5.3), Too much to list, there are more machines

Posted on Jun 22, 2009 12:24 PM

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Answer 1

Jun 24, 2009 4:33 AM in response to mguertin

You've got VPN working tethered using a L2PT tunnel on the Rogers network? Interesting.

Read this post:

http://discussions.apple.com/thread.jspa?threadID=2050206

I'm assuming you are using the OS built-in VPN L2TP feature to create the tunnel? Are you able to mount shares on the LAN-side without any issues? Using the Cisco client on the MacBook Pro to create the tunnel successfully creates the VPN connection, but you can't do anything on the Internet - no browsing, no mounting shares, nothing. Very odd.

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Answer 2

mguertin Author

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Jun 24, 2009 6:01 AM in response to Derek Cooper2

Yes, using built-in OSX client and connecting to Leopard server using MS-CHAP authentication. I haven't tried mounting shares through the tunnel yet, but I have both ssh'ed and VNC'ed without problems.

The sales rep you spoke with was either mis-informed, or Apple doesn't "officially" support VPN while tethered ... quite a few people I've found on other forums have VPN working with tether from Rogers and Fido. No one with PPTP yet though 😟

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Answer 3

Jun 24, 2009 6:12 AM in response to mguertin

Do you have links to other forums documenting their attempts? We're using a Cisco firewall, which is a wee bit different from the Leopard server.

Could you try mounting shares - CIFS and AFP - to see if those work? That'd be great.

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Answer 4

Jun 24, 2009 10:12 AM in response to Derek Cooper2

Got it working! Here are the details for others who are trying: Rogers network with Public IP feature, tether to a MacBook Pro, then launch the Cisco VPN client and connect. My Cisco tech was able to modify the settings on the firewall to ensure it'd all work!

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Answer 5

mguertin Author

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Jun 24, 2009 6:04 PM in response to Derek Cooper2

Glad you got your setup working, I'm still having no luck at all with PPTP VPN setups.

Anyone?

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Answer 6

qyo001

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Jun 26, 2009 8:46 AM in response to mguertin

I've got the same problem with PPTP VPN .
I see in wireshark that it stuck in "PPP LCP Configuration Request" (I see this REQ going from my laptop to iPhone ) , but there is no Config Reply ... so not sure if it's blocked on the iPhone itself or on Rogers firewall . I called Rogers , they said we don't block VPN's on our 3G network and asked me to call Apple ... Would be nice to get traces from iPhone itself... but don't like to jailbreak it 😟

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Answer 7

mguertin Author

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Jun 26, 2009 8:54 AM in response to qyo001

PPTP VPN works with the iPhone client for me over 3G (once I got the public IP address option enabled on my Rogers account).

I'm seeing pretty much the exact same behaviour here, I'm assuming that the iPhone tethering (NAT) is not passing along GRE. Hopefully they resolve this sooner than later as pretty much any modern "router" has this option enabled by default -- and that is pretty much what tethering is supplying to us .. a handy 3G "router".

Yes it would be very handy to be able to snoop the packets on the iPhone itself, then at least we would be able to find ourselves a proper answer 😟 It's kind of annoying when no one is willing to take the blame or support this option. They are happy to charge you the $$ to enable what you need, but if you need help actually making it work, good luck. Last word from Rogers was "Contact your system administrator." ... I replied "I AM the system administrator" ... then there was a long silence and they asked me if they could help me with anything else 😟

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Answer 8

Jun 26, 2009 11:35 AM in response to qyo001

This is not true... the Rogers default APN "INTERNET.COM" does not support PPTP VPN connections. I am having this issue from the iPhone itself so I can assume tethering will be affected the same way. You must purchase the $10 per month VPN option and use the Apple iPhone Configuration Utility to change the APN to "VPN.COM". Changing the APN is an advanced setting which can not be done on the phone itself.

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Answer 9

mguertin Author

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Jun 26, 2009 12:05 PM in response to mrchartier

I have in fact done both of these things already as I stated in the first post. I have purchased the "public IP" option from Rogers and it is enabled on my account. I've also made a custom profile with the configuration utility and changed my APN as you stated. I have a working public IP but the iPhone tethering/NAT is NOT passing GRE as far as I can tell. IPSec and L2TP based VPN's are working fine for me, PPTN is not.

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Answer 10

qyo001

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Jun 26, 2009 1:32 PM in response to mguertin

Question about public IP.
I did change my profile to vpn.com , no problem , but I don't see the difference. In either cases it shows me that I use the same IP address (74.198.12.14) , in both cases I can go to internet but not do PPTP with tethering. I did not buy the "VPN support" from Rogers, why I still can use the apn "vpn.com"? Rogers HLR should decline me and not forward my requests to anywhere if I don't have a subscription for it.... Confused....

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Answer 11

mguertin Author

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Jun 26, 2009 1:35 PM in response to qyo001

You have to buy the public IP package from Rogers before the public IP will properly work (even if you've changed your APN it doesn't work until you pay for it)

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