Mac VPN different subnet masks

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kohut124

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Nov 19, 2014
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Hey guys so I'm having trouble with a VPN.


Mac OS X Maverick
protocols: PPTP / SSTP
The server is running Windows.

Issue:
The server which the company doesn't want to change has a different subnet than the Mac's

Server subnet: 255.255.255.0
Mac subnet: 255.255.0.0(hard coded).
So basically the IP range is different.

So I can connect to the VPN but I'm unable to view other computers on the network.

My solution so far is to find a 3rd party VPN client or any other solutions if someone will offer.

I have very basic knowledge about macs, I'm a Windows guy :(

 
Solution
B
so say the server is on on 192.168.1.100/24 (net mask would be 255.255.255.0) and the mac was on 192.168.1.200/16 (netmask 255.255.0.0). this would be a weird setup I think but they would both think they were on the same network. Now imagine the mac was 192.168.2.100/16 (netmask would still be 255.255.0.0). then the mac trying to reach the server would think the server is still on the same network, while the server would think the mac was on a different network and traffic would be sent out the internet gateway. In this case, with the private IP addresses, traffic from the server to the mac would probably never make it to the mac since private IP addresses are non routable.

and actually, depending on your network architecture...
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bliq

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Jun 29, 2006
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the subnet isn't a windows or mac thing, it's a networking thing. essentially the server thinks anything with the same first three octets is on the local network (as many as 254 IP addresses). the mac thinks anything with the same first two octets is on the local network (about 16K IPs)

as to why you can't view other computers on the network, that's a more of a networking question and possibly a firewall (network and or OS level) issue.
 
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K

kohut124

Honorable
Nov 19, 2014
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Right, so the subnet mask wouldn't have anything to do with the computers seeing each other? since I need them all on the same local network. If the server is on one subnet(ex: 255.255.255.0) and the mac is on (255.255.0.0.) then technically they are considered on different local networks..?

The Mac connects and will ping the vpn server, but have no communication with the server we're trying to connect to.
 
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bliq

Distinguished
Jun 29, 2006
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0
20,160
so say the server is on on 192.168.1.100/24 (net mask would be 255.255.255.0) and the mac was on 192.168.1.200/16 (netmask 255.255.0.0). this would be a weird setup I think but they would both think they were on the same network. Now imagine the mac was 192.168.2.100/16 (netmask would still be 255.255.0.0). then the mac trying to reach the server would think the server is still on the same network, while the server would think the mac was on a different network and traffic would be sent out the internet gateway. In this case, with the private IP addresses, traffic from the server to the mac would probably never make it to the mac since private IP addresses are non routable.

and actually, depending on your network architecture, unless the server was actually in the same network as the mac, traffic from mac to server may not make it either.

probably the best way to figure this out is to actually post network configurations and some details of architecture if you have them and if you're allowed to.
 
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