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I've setup pptp server on cisco router today. The remote client IP addresses are assigned on this cisco router by DHCP. Also I set up option 249 and 121 to provide classless routing for my VPN clients.

Option 249 and 121 used for two routes: 10.0.0.0/8 and 192.168.0.0/16.

I've tested this configuration on my Windows XP and Mac OS X Snow Leopard. All working just fine.

But my Windows 7 computer gets only the first address from the option 121 and ignores the next one. Why?

How I can fix it or trace/debug it?

Configuration of dhcp pool is:

ip dhcp pool pptp-users
  network 10.255.241.0 255.255.255.0
  default-router 10.255.241.1
  dns-server 10.255.249.40
  netbios-name-server 10.255.249.40
  option 249 hex 080a.0aff.f101.10c0.a80a.fff1.01
  option 121 hex 080a.0aff.f101.10c0.a80a.fff1.01

If I change routes in the option all works the same way. Windows XP and MacOS X works. Windows 7 just got the second one route 10.0.0.0/8

Routing table before pptp connection

===========================================================================
Interface List
 14...00 ff 52 b7 58 e0 ......TAP-Win32 Adapter V9
 13...90 4c e5 e0 f9 a6 ......11b/g/n  Wireless LAN Mini-PCI Express Adapter II
 11...00 26 2d f1 3d cd ......Intel(R) 82577LM Gigabit Network Connection
  1...........................Software Loopback Interface 1
 19...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter
 12...00 00 00 00 00 00 00 e0 Teredo Tunneling Pseudo-Interface
 20...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter #2
 34...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter #4
===========================================================================

IPv4 Route Table
===========================================================================
Active Routes:
Network Destination        Netmask          Gateway       Interface  Metric
          0.0.0.0          0.0.0.0       172.16.1.1     172.16.1.105     25
        127.0.0.0        255.0.0.0         On-link         127.0.0.1    306
        127.0.0.1  255.255.255.255         On-link         127.0.0.1    306
  127.255.255.255  255.255.255.255         On-link         127.0.0.1    306
       172.16.1.0    255.255.255.0         On-link      172.16.1.105    281
     172.16.1.105  255.255.255.255         On-link      172.16.1.105    281
     172.16.1.255  255.255.255.255         On-link      172.16.1.105    281
        224.0.0.0        240.0.0.0         On-link         127.0.0.1    306
        224.0.0.0        240.0.0.0         On-link      172.16.1.105    281
  255.255.255.255  255.255.255.255         On-link         127.0.0.1    306
  255.255.255.255  255.255.255.255         On-link      172.16.1.105    281
===========================================================================
Persistent Routes:
  Network Address          Netmask  Gateway Address  Metric
          0.0.0.0          0.0.0.0   184.191.32.135  Default 
===========================================================================

IPv6 Route Table
===========================================================================
Active Routes:
 If Metric Network Destination      Gateway
 12     58 ::/0                     On-link
 12     58 2001::/32                On-link
 12    306 2001:0:4137:9e76:1c98:1713:b83a:3ffc/128
                                    On-link
 12    306 fe80::/64                On-link
 19    286 fe80::5efe:172.16.1.105/128
                                    On-link
 12    306 fe80::1c98:1713:b83a:3ffc/128
                                    On-link
===========================================================================
Persistent Routes:
  None

Routing table after pptp connection

===========================================================================
Interface List
 21...........................VPN Connection
 14...00 ff 52 b7 58 e0 ......TAP-Win32 Adapter V9
 13...90 4c e5 e0 f9 a6 ......11b/g/n  Wireless LAN Mini-PCI Express Adapter II
 11...00 26 2d f1 3d cd ......Intel(R) 82577LM Gigabit Network Connection
  1...........................Software Loopback Interface 1
 19...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter
 12...00 00 00 00 00 00 00 e0 Teredo Tunneling Pseudo-Interface
 20...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter #2
 17...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter #3
 34...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter #4
===========================================================================

IPv4 Route Table
===========================================================================
Active Routes:
Network Destination        Netmask          Gateway       Interface  Metric
          0.0.0.0          0.0.0.0       172.16.1.1     172.16.1.105     25
         10.0.0.0        255.0.0.0     10.255.241.1    10.255.241.57     26
    10.255.241.57  255.255.255.255         On-link     10.255.241.57    281
    96.31.168.206  255.255.255.255       172.16.1.1     172.16.1.105     26
        127.0.0.0        255.0.0.0         On-link         127.0.0.1    306
        127.0.0.1  255.255.255.255         On-link         127.0.0.1    306
  127.255.255.255  255.255.255.255         On-link         127.0.0.1    306
       172.16.1.0    255.255.255.0         On-link      172.16.1.105    281
     172.16.1.105  255.255.255.255         On-link      172.16.1.105    281
     172.16.1.255  255.255.255.255         On-link      172.16.1.105    281
        224.0.0.0        240.0.0.0         On-link         127.0.0.1    306
        224.0.0.0        240.0.0.0         On-link      172.16.1.105    281
  255.255.255.255  255.255.255.255         On-link         127.0.0.1    306
  255.255.255.255  255.255.255.255         On-link      172.16.1.105    281
  255.255.255.255  255.255.255.255         On-link     10.255.241.57    281
===========================================================================
Persistent Routes:
  Network Address          Netmask  Gateway Address  Metric
          0.0.0.0          0.0.0.0   184.191.32.135  Default 
===========================================================================
IPv6 Route Table
===========================================================================
Active Routes:
 If Metric Network Destination      Gateway
 19    286 fe80::5efe:172.16.1.105/128
                                    On-link
===========================================================================
Persistent Routes:
  None
share|improve this question
    
what happens if swap these routes? if you try to manually set route for second network? – gelraen Jan 25 '11 at 20:02
    
If I swap these routes I got all the same. WinXP and MacOS X works fine. Windows 7 got second one (10.0.0.0/8) only. If I set this route manually on Windows 7 it's working fine. – pchel Jan 25 '11 at 23:12
    
Windows 7 is connected to any subnet from 192.168/16? Can you show it's routing table before connecting to your PPTP server? – gelraen Jan 26 '11 at 8:30
    
gelraen, No. I updated the post with routing table. – pchel Jan 28 '11 at 19:22

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