About to "VPN" my MAC to Waste Management...

T

thasatelliteguy

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I have setup a SBS2003 server at my office. I have setup VPN on a dedicated NIC, dedicated public IP, dedicated port straight to the web. I, as well as my boss can connect thru a variety of locales, and a variety of ISPs to the vpn. It is super stable and works perfectly IF we're on a PC. I have been trying for a week solid to make my MAC connect with zero success. It just keeps telling me the server isn't responding. I have tried Digitunnel, same thing. What do I have to do to make Steve talk to Bill?
 
It would help if you posted your Mac's version of OS X. Plus please post if you are using a third party VPN on the Mac or the 10.6 built-in VPN.
 
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Sorry for the lack of details.....

Snow Leopard. I'm not at home right now, but I beleive it's 10.6.x

I have tried the built in VPN for MAC, and last night found a trial version of Digitunnel. Both do the same thing.

I'm also not positive if I'm setup on the server as PPTP or IPSEC. I'm nearly positive that it's PPTP. I just ran thru the setup for RRAS in Windows and enabled the users I needed to use remote connections and it worked really surprisingly easily.

If I try to connect this way on my MAC, it says the server isnt responding. If I try IPsec, it says I have no secret.
 
What address are you using to connect to the VPN server?

Are your credentials (username/password) correct?

Are you authenticating to an Active Directory forest/domain?
 
I can use my vpn.domain.com or the actual IP address. No difference. Both work on a PC, both fail on MAC.

UN/PW again, works on PC.

I do not enter a domain name or anything to connect on my PC. Just UN/PW and server address and it logs in.
 
I guess I just cant understand why this seems to be so difficult. VPNs are not a new idea, and it's a function built in to the OS, and since there are so few MAC servers, why is it so hard to get my MAC to login to a 2k3 VPN server??
 
It's really tough to say without actually seeing the VPN setup you've got going on -- on both the Mac and the Windows computer.

I can say that a simple PPTP VPN set up on a Windows 2k3 server with the proper ports forwarded does work fine on my end, on all my Macs.

Maybe your Windows domain has strict domain credentials enforced -- try inputting your username as "DOMAIN\username"... if your domain was called "MYDOMAIN" and your username is "myusername" put your username in the Mac VPN setup as "MYDOMAIN\myusername" and see if that helps.

Other than that, I can't think why it's not connecting... would it be possible to talk with the manager of that Windows server and find out exactly and precisely what the VPN is set up as? PPTP vs. ipSec, etc?
 
thasatelliteguy said:
Sorry for the lack of details.....

Snow Leopard. I'm not at home right now, but I beleive it's 10.6.x

I have tried the built in VPN for MAC, and last night found a trial version of Digitunnel. Both do the same thing.
Click to expand...

Well DigiTunnel hasn't been updated since 10.4.x.

I found this example on the internal 10.6 VPN setup, so it might help. Try it to see if this works.
 
Ok. I have more information...

First, I am the manager of the windows server. I am somewhat inexperienced, but here's what I know so far. I followed Bill's directions on how to setup RRAS. I just searched out info on setting up IPsec vs PPTP, and from the long-winded setup procedures I found, I can assure you it's NOT IPsec. My setup was very quick and simple. I was actually shocked at how easy it was. (I also realize it's 'ease' probly means there's security lacking somewhere, but we have nothing the chinese goverment is interested in!)

Second, I believe the server is using Active Directory. I would prefer it not, as I only really need a simple P2P network in the office with some centralized file storage/backup and maybe VPN, webserver, and maybe an FTP server. However, windows installs it as a domain, and the last time I tried to undo that, it stalled in the middle, and then locked me out. There were no longer ANY valid credentials to logon with and I had to wipe the server and start all over.

Third, my username is like "Bill Gates". In the user properties it shows User Logon name as Bill Gates. Next to it, in another box says @company.local. Under that, it says pre-2000 logon Company\Bill Gates. When I attempt to create a VPN connection in any version of windows, I simply enter the IP or vpn.company.com (which I have dns forwarded) and name the connection. Then it asks for username and password. I enter "Bill Gates" in username, and "password" in the password and leave the domain box empty. It logs in quickly and easily, no problem. Any variation to that and it fails. Such as username Bill Gates@company.local or Bill Gates@company or Company\Bill Gates or putting company or company.local in the domain box. So again, I'm stumped. Also, just realized, duh, my VPN connection in Vista says WAN miniport PPTP.

If anyone out there would like to help, I would consider creating a temporary server/vpn account to take a look, cuz I think this should work as it is, but maybe I'm missing something.
 
Would you mind setting up a temp server/VPN account? I can and would be willing to test with both Windows XP clients and Mac clients alike and see if I encounter the same issues you do.

You can private message me the credentials if you like on this forum. Let me know if you're familiar with private messages here and, if not, I'll walk you through them.
 
If you are using the Cisco VPN client on a NEW Mac Book Pro or 64 bit OS X you must boot into 32 bit mode (on 64 Bit OS X machines boot while holding down the keys 3+2 while booting up, to boot in 32 bit mode). The Cisco VPN client is 32 bit and in 64 Bit OS x system will give out error codes when using their client. Then try booting into 32 bit mode and see if the Cisco VPN client works.
 
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