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I'm probably doing something incredibly stupid, but I just can't seem to figure out what. Here's what I'm trying to accomplish: I want remote users to be able to log into our network, so I set up a Windows 2008 Server as a VPN Server inside as a VM in XenCenter. Let's call him Benjamin. He's also doubling as a file server.

So far, what works:

  • Remote VPN Login with Mac, Windows and iOS Clients
  • Access to the file shares on Benjamin
  • Ping to all hosts on the local network and on the internet, even with big packets (>1000 bytes)

What doesn't: I can't establish any TCP connection (SSH, HTTP, …) to hosts on the local network besides Benjamin itself. In Wireshark, I can see the SYN and SYN-ACKs on both the client and the computer I'm trying to reach, but there's never an ACK. (Funnily, in the Wireshark Logs I prepared there are some DUP ACKs for some reason - and they are exactly the wrong way around than how it should be. I have no idea why.)

There was a problem before with even pinging anything besides Benjamin, but I solved that by disabling IP checksum offloading on Benjamin (somehow it didn't work and then packets would be thrown away).

I tried setting really small MTUs on my client, setting the gateway to Benjamin on the computer in the internal network any lots of other stuff, but nothing helped.

I suspect it's some kind of routing issue, but those ACKs are nowhere to be found. Any ideas? Where should I investigate further? Thanks in advance!

Update: Weird thing I just discovered: When I try to ssh from the internal network into the VPN client, the client gets the SYN (I see it in Wireshark), but again, he never responds. I get the feeling that it has to be some configuration issue on the clients, but on all of them? And what could it be? There's no Firewall, and according to Wireshark, the packet looks valid (checksum and all). Does anyone know why it wouldn't respond to neither a SYN nor a SYN-ACK, when there's no firewall which could throw away those packets?

Update 2: To add to the confusion, I've just confirmed that using netcat and UDP, everything works correctly, in both directions (nc listening on internal network host and on the VPN client). Maybe TCP just doesn't like me anymore?

Here's some more information:

Local net:   172.17.0.0/16
Router:     172.17.0.1 (Port Forwarding TCP 1701, UDP 500 and 4500)
XenServer:  172.17.0.10
Benjamin:   172.17.1.1
VPN DHCP range: 172.17.7.1..240

Wireshark log on the client (172.17.7.2 when in the VPN):

No.     Time        Source                Destination           Protocol Length Info
      1 0.000000    172.17.4.4            172.17.7.2            TCP      68     ssh > 61653 [SYN, ACK] Seq=0 Ack=0 Win=65535 Len=0 MSS=1060 WS=4 TSval=1641695654 TSecr=440887504 SACK_PERM=1

Frame 1: 68 bytes on wire (544 bits), 68 bytes captured (544 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61653 (61653), Seq: 0, Ack: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      2 5.337197    172.17.7.2            172.17.4.4            TCP      68     61655 > ssh [SYN] Seq=0 Win=65535 Len=0 MSS=1240 WS=8 TSval=440887658 TSecr=0 SACK_PERM=1

Frame 2: 68 bytes on wire (544 bits), 68 bytes captured (544 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.7.2 (172.17.7.2), Dst: 172.17.4.4 (172.17.4.4)
Transmission Control Protocol, Src Port: 61655 (61655), Dst Port: ssh (22), Seq: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      3 5.479947    172.17.4.4            172.17.7.2            TCP      68     ssh > 61655 [SYN, ACK] Seq=0 Ack=1 Win=65535 Len=0 MSS=1060 WS=4 TSval=1641701208 TSecr=440887658 SACK_PERM=1

Frame 3: 68 bytes on wire (544 bits), 68 bytes captured (544 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 0, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      4 6.256638    172.17.7.2            172.17.4.4            TCP      68     61655 > ssh [SYN] Seq=0 Win=65535 Len=0 MSS=1240 WS=8 TSval=440887667 TSecr=0 SACK_PERM=1

Frame 4: 68 bytes on wire (544 bits), 68 bytes captured (544 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.7.2 (172.17.7.2), Dst: 172.17.4.4 (172.17.4.4)
Transmission Control Protocol, Src Port: 61655 (61655), Dst Port: ssh (22), Seq: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      5 6.449901    172.17.4.4            172.17.7.2            TCP      56     [TCP Dup ACK 3#1] ssh > 61655 [ACK] Seq=1 Ack=1 Win=262140 Len=0 TSval=1641702152 TSecr=440887667

Frame 5: 56 bytes on wire (448 bits), 56 bytes captured (448 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 1, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      6 6.609908    172.17.4.4            172.17.7.2            TCP      68     ssh > 61655 [SYN, ACK] Seq=0 Ack=1 Win=65535 Len=0 MSS=1060 WS=4 TSval=1641702305 TSecr=440887667 SACK_PERM=1

Frame 6: 68 bytes on wire (544 bits), 68 bytes captured (544 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 0, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      7 7.258316    172.17.7.2            172.17.4.4            TCP      68     61655 > ssh [SYN] Seq=0 Win=65535 Len=0 MSS=1240 WS=8 TSval=440887677 TSecr=0 SACK_PERM=1

Frame 7: 68 bytes on wire (544 bits), 68 bytes captured (544 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.7.2 (172.17.7.2), Dst: 172.17.4.4 (172.17.4.4)
Transmission Control Protocol, Src Port: 61655 (61655), Dst Port: ssh (22), Seq: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      8 7.450032    172.17.4.4            172.17.7.2            TCP      56     [TCP Dup ACK 6#1] ssh > 61655 [ACK] Seq=1 Ack=1 Win=262140 Len=0 TSval=1641703139 TSecr=440887677

Frame 8: 56 bytes on wire (448 bits), 56 bytes captured (448 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 1, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      9 8.259938    172.17.7.2            172.17.4.4            TCP      68     61655 > ssh [SYN] Seq=0 Win=65535 Len=0 MSS=1240 WS=8 TSval=440887687 TSecr=0 SACK_PERM=1

Frame 9: 68 bytes on wire (544 bits), 68 bytes captured (544 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.7.2 (172.17.7.2), Dst: 172.17.4.4 (172.17.4.4)
Transmission Control Protocol, Src Port: 61655 (61655), Dst Port: ssh (22), Seq: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     10 8.490122    172.17.4.4            172.17.7.2            TCP      56     [TCP Dup ACK 6#2] ssh > 61655 [ACK] Seq=1 Ack=1 Win=262140 Len=0 TSval=1641704143 TSecr=440887687

Frame 10: 56 bytes on wire (448 bits), 56 bytes captured (448 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 1, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     11 9.249943    172.17.4.4            172.17.7.2            TCP      68     ssh > 61655 [SYN, ACK] Seq=0 Ack=1 Win=65535 Len=0 MSS=1060 WS=4 TSval=1641704904 TSecr=440887687 SACK_PERM=1

Frame 11: 68 bytes on wire (544 bits), 68 bytes captured (544 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 0, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     12 9.261766    172.17.7.2            172.17.4.4            TCP      68     61655 > ssh [SYN] Seq=0 Win=65535 Len=0 MSS=1240 WS=8 TSval=440887697 TSecr=0 SACK_PERM=1

Frame 12: 68 bytes on wire (544 bits), 68 bytes captured (544 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.7.2 (172.17.7.2), Dst: 172.17.4.4 (172.17.4.4)
Transmission Control Protocol, Src Port: 61655 (61655), Dst Port: ssh (22), Seq: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     13 9.430047    172.17.4.4            172.17.7.2            TCP      56     [TCP Dup ACK 11#1] ssh > 61655 [ACK] Seq=1 Ack=1 Win=262140 Len=0 TSval=1641705119 TSecr=440887697

Frame 13: 56 bytes on wire (448 bits), 56 bytes captured (448 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 1, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     14 10.263852   172.17.7.2            172.17.4.4            TCP      68     61655 > ssh [SYN] Seq=0 Win=65535 Len=0 MSS=1240 WS=8 TSval=440887707 TSecr=0 SACK_PERM=1

Frame 14: 68 bytes on wire (544 bits), 68 bytes captured (544 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.7.2 (172.17.7.2), Dst: 172.17.4.4 (172.17.4.4)
Transmission Control Protocol, Src Port: 61655 (61655), Dst Port: ssh (22), Seq: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     15 10.439839   172.17.4.4            172.17.7.2            TCP      56     [TCP Dup ACK 11#2] ssh > 61655 [ACK] Seq=1 Ack=1 Win=262140 Len=0 TSval=1641706132 TSecr=440887707

Frame 15: 56 bytes on wire (448 bits), 56 bytes captured (448 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 1, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     16 12.267344   172.17.7.2            172.17.4.4            TCP      68     61655 > ssh [SYN] Seq=0 Win=65535 Len=0 MSS=1240 WS=8 TSval=440887727 TSecr=0 SACK_PERM=1

Frame 16: 68 bytes on wire (544 bits), 68 bytes captured (544 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.7.2 (172.17.7.2), Dst: 172.17.4.4 (172.17.4.4)
Transmission Control Protocol, Src Port: 61655 (61655), Dst Port: ssh (22), Seq: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     17 12.469629   172.17.4.4            172.17.7.2            TCP      56     [TCP Dup ACK 11#3] ssh > 61655 [ACK] Seq=1 Ack=1 Win=262140 Len=0 TSval=1641708126 TSecr=440887727

Frame 17: 56 bytes on wire (448 bits), 56 bytes captured (448 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 1, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     18 16.719912   172.17.4.4            172.17.7.2            TCP      68     ssh > 61653 [SYN, ACK] Seq=0 Ack=0 Win=65535 Len=0 MSS=1060 WS=4 TSval=1641712353 TSecr=440887504 SACK_PERM=1

Frame 18: 68 bytes on wire (544 bits), 68 bytes captured (544 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61653 (61653), Seq: 0, Ack: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     19 21.679611   172.17.4.4            172.17.7.2            TCP      68     ssh > 61655 [SYN, ACK] Seq=0 Ack=1 Win=65535 Len=0 MSS=1060 WS=4 TSval=1641717388 TSecr=440887727 SACK_PERM=1

Frame 19: 68 bytes on wire (544 bits), 68 bytes captured (544 bits)
Point-to-Point Protocol
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 0, Ack: 1, Len: 0

Wireshark log in the computer in the local network (172.17.4.4):

No.     Time        Source                Destination           Protocol Length Info
      1 0.000000    172.17.7.2            172.17.4.4            TCP      78     61655 > ssh [SYN] Seq=0 Win=65535 Len=0 MSS=1240 WS=8 TSval=440887658 TSecr=0 SACK_PERM=1

Frame 1: 78 bytes on wire (624 bits), 78 bytes captured (624 bits)
Ethernet II, Src: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec), Dst: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff)
Internet Protocol Version 4, Src: 172.17.7.2 (172.17.7.2), Dst: 172.17.4.4 (172.17.4.4)
Transmission Control Protocol, Src Port: 61655 (61655), Dst Port: ssh (22), Seq: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      2 0.000102    172.17.4.4            172.17.7.2            TCP      78     ssh > 61655 [SYN, ACK] Seq=0 Ack=1 Win=65535 Len=0 MSS=1060 WS=4 TSval=1641701208 TSecr=440887658 SACK_PERM=1

Frame 2: 78 bytes on wire (624 bits), 78 bytes captured (624 bits)
Ethernet II, Src: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff), Dst: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec)
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 0, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      3 0.950403    172.17.7.2            172.17.4.4            TCP      78     61655 > ssh [SYN] Seq=0 Win=65535 Len=0 MSS=1240 WS=8 TSval=440887667 TSecr=0 SACK_PERM=1

Frame 3: 78 bytes on wire (624 bits), 78 bytes captured (624 bits)
Ethernet II, Src: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec), Dst: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff)
Internet Protocol Version 4, Src: 172.17.7.2 (172.17.7.2), Dst: 172.17.4.4 (172.17.4.4)
Transmission Control Protocol, Src Port: 61655 (61655), Dst Port: ssh (22), Seq: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      4 0.950567    172.17.4.4            172.17.7.2            TCP      66     [TCP Dup ACK 2#1] ssh > 61655 [ACK] Seq=1 Ack=1 Win=262140 Len=0 TSval=1641702152 TSecr=440887667

Frame 4: 66 bytes on wire (528 bits), 66 bytes captured (528 bits)
Ethernet II, Src: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff), Dst: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec)
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 1, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      5 1.104130    172.17.4.4            172.17.7.2            TCP      78     ssh > 61655 [SYN, ACK] Seq=0 Ack=1 Win=65535 Len=0 MSS=1060 WS=4 TSval=1641702305 TSecr=440887667 SACK_PERM=1

Frame 5: 78 bytes on wire (624 bits), 78 bytes captured (624 bits)
Ethernet II, Src: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff), Dst: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec)
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 0, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      6 1.940779    172.17.7.2            172.17.4.4            TCP      78     61655 > ssh [SYN] Seq=0 Win=65535 Len=0 MSS=1240 WS=8 TSval=440887677 TSecr=0 SACK_PERM=1

Frame 6: 78 bytes on wire (624 bits), 78 bytes captured (624 bits)
Ethernet II, Src: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec), Dst: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff)
Internet Protocol Version 4, Src: 172.17.7.2 (172.17.7.2), Dst: 172.17.4.4 (172.17.4.4)
Transmission Control Protocol, Src Port: 61655 (61655), Dst Port: ssh (22), Seq: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      7 1.940962    172.17.4.4            172.17.7.2            TCP      66     [TCP Dup ACK 5#1] ssh > 61655 [ACK] Seq=1 Ack=1 Win=262140 Len=0 TSval=1641703139 TSecr=440887677

Frame 7: 66 bytes on wire (528 bits), 66 bytes captured (528 bits)
Ethernet II, Src: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff), Dst: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec)
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 1, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      8 2.950009    172.17.7.2            172.17.4.4            TCP      78     61655 > ssh [SYN] Seq=0 Win=65535 Len=0 MSS=1240 WS=8 TSval=440887687 TSecr=0 SACK_PERM=1

Frame 8: 78 bytes on wire (624 bits), 78 bytes captured (624 bits)
Ethernet II, Src: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec), Dst: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff)
Internet Protocol Version 4, Src: 172.17.7.2 (172.17.7.2), Dst: 172.17.4.4 (172.17.4.4)
Transmission Control Protocol, Src Port: 61655 (61655), Dst Port: ssh (22), Seq: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
      9 2.950198    172.17.4.4            172.17.7.2            TCP      66     [TCP Dup ACK 5#2] ssh > 61655 [ACK] Seq=1 Ack=1 Win=262140 Len=0 TSval=1641704143 TSecr=440887687

Frame 9: 66 bytes on wire (528 bits), 66 bytes captured (528 bits)
Ethernet II, Src: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff), Dst: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec)
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 1, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     10 3.714242    172.17.4.4            172.17.7.2            TCP      78     ssh > 61655 [SYN, ACK] Seq=0 Ack=1 Win=65535 Len=0 MSS=1060 WS=4 TSval=1641704904 TSecr=440887687 SACK_PERM=1

Frame 10: 78 bytes on wire (624 bits), 78 bytes captured (624 bits)
Ethernet II, Src: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff), Dst: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec)
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 0, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     11 3.929627    172.17.7.2            172.17.4.4            TCP      78     61655 > ssh [SYN] Seq=0 Win=65535 Len=0 MSS=1240 WS=8 TSval=440887697 TSecr=0 SACK_PERM=1

Frame 11: 78 bytes on wire (624 bits), 78 bytes captured (624 bits)
Ethernet II, Src: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec), Dst: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff)
Internet Protocol Version 4, Src: 172.17.7.2 (172.17.7.2), Dst: 172.17.4.4 (172.17.4.4)
Transmission Control Protocol, Src Port: 61655 (61655), Dst Port: ssh (22), Seq: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     12 3.929819    172.17.4.4            172.17.7.2            TCP      66     [TCP Dup ACK 10#1] ssh > 61655 [ACK] Seq=1 Ack=1 Win=262140 Len=0 TSval=1641705119 TSecr=440887697

Frame 12: 66 bytes on wire (528 bits), 66 bytes captured (528 bits)
Ethernet II, Src: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff), Dst: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec)
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 1, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     13 4.949931    172.17.7.2            172.17.4.4            TCP      78     61655 > ssh [SYN] Seq=0 Win=65535 Len=0 MSS=1240 WS=8 TSval=440887707 TSecr=0 SACK_PERM=1

Frame 13: 78 bytes on wire (624 bits), 78 bytes captured (624 bits)
Ethernet II, Src: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec), Dst: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff)
Internet Protocol Version 4, Src: 172.17.7.2 (172.17.7.2), Dst: 172.17.4.4 (172.17.4.4)
Transmission Control Protocol, Src Port: 61655 (61655), Dst Port: ssh (22), Seq: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     14 4.950122    172.17.4.4            172.17.7.2            TCP      66     [TCP Dup ACK 10#2] ssh > 61655 [ACK] Seq=1 Ack=1 Win=262140 Len=0 TSval=1641706132 TSecr=440887707

Frame 14: 66 bytes on wire (528 bits), 66 bytes captured (528 bits)
Ethernet II, Src: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff), Dst: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec)
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 1, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     15 6.950093    172.17.7.2            172.17.4.4            TCP      78     61655 > ssh [SYN] Seq=0 Win=65535 Len=0 MSS=1240 WS=8 TSval=440887727 TSecr=0 SACK_PERM=1

Frame 15: 78 bytes on wire (624 bits), 78 bytes captured (624 bits)
Ethernet II, Src: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec), Dst: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff)
Internet Protocol Version 4, Src: 172.17.7.2 (172.17.7.2), Dst: 172.17.4.4 (172.17.4.4)
Transmission Control Protocol, Src Port: 61655 (61655), Dst Port: ssh (22), Seq: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     16 6.950281    172.17.4.4            172.17.7.2            TCP      66     [TCP Dup ACK 10#3] ssh > 61655 [ACK] Seq=1 Ack=1 Win=262140 Len=0 TSval=1641708126 TSecr=440887727

Frame 16: 66 bytes on wire (528 bits), 66 bytes captured (528 bits)
Ethernet II, Src: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff), Dst: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec)
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 1, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     17 7.955752    172.17.4.4            172.17.7.2            TCP      78     ssh > 61655 [SYN, ACK] Seq=0 Ack=1 Win=65535 Len=0 MSS=1060 WS=4 TSval=1641709126 TSecr=440887727 SACK_PERM=1

Frame 17: 78 bytes on wire (624 bits), 78 bytes captured (624 bits)
Ethernet II, Src: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff), Dst: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec)
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 0, Ack: 1, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     18 11.196585   172.17.4.4            172.17.7.2            TCP      78     ssh > 61653 [SYN, ACK] Seq=0 Ack=0 Win=65535 Len=0 MSS=1060 WS=4 TSval=1641712353 TSecr=440887504 SACK_PERM=1

Frame 18: 78 bytes on wire (624 bits), 78 bytes captured (624 bits)
Ethernet II, Src: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff), Dst: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec)
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61653 (61653), Seq: 0, Ack: 0, Len: 0

No.     Time        Source                Destination           Protocol Length Info
     19 16.252632   172.17.4.4            172.17.7.2            TCP      78     ssh > 61655 [SYN, ACK] Seq=0 Ack=1 Win=65535 Len=0 MSS=1060 WS=4 TSval=1641717388 TSecr=440887727 SACK_PERM=1

Frame 19: 78 bytes on wire (624 bits), 78 bytes captured (624 bits)
Ethernet II, Src: Apple_4e:5b:ff (c8:2a:14:4e:5b:ff), Dst: c6:4f:51:a3:48:ec (c6:4f:51:a3:48:ec)
Internet Protocol Version 4, Src: 172.17.4.4 (172.17.4.4), Dst: 172.17.7.2 (172.17.7.2)
Transmission Control Protocol, Src Port: ssh (22), Dst Port: 61655 (61655), Seq: 0, Ack: 1, Len: 0

Potentially related server fault questions, but didn't help me so far:

PPTP-Gateway routes icmp but no http

SNAT through Racoon IPSec VPN

Linux fails to interpret ACK, keeps resending SYN+ACK

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1 Answer 1

I would start by taking a look at your masking. If the general hosts are in 172.17.0.0/16 and your VPN subnet is in 172.17.7.0/24 then it's entirely possible for there to be some uncertain connectivity situations.

A general host in 172.17.0.0/16 when sending a packet to a VPN host in 172.17.7.0/24 will attempt to ARP for the VPN host's address (rather than sending it to a gateway).

The VPN host, in turn, tries to send a frame to a host in the general subnet. It's going to send via its gateway. If this gateway is a member of both the /24 and the /16 then you've got a similar problem - either it's an illegal configuration or the packet is actually being bridged rather than routed.

It's possible you have proxy-arp configured - that would cause a routing device to answer ARP requests in the larger subnet for a host it has a route to, but this isn't clear from your posted materials.

It's also possible that you have bridging set up somewhere in the mix. This could yield some strange situations as a standard ARP would work in one direction but in the other some sort of gateway would be called upon to forward a nominally routed frame back out the receiving interface - which, again, might work in some circumstances but isn't good (nb - this could be a source of duplicate ACK's).

Can you put your VPN hosts in a non-overlapping subnet? Say give it a 172.18.x.x address and then configure routing between the gateway for this new subnet and the default gateway for 172.17.0.0/16? At a minimum this would make the whole thing simpler to troubleshoot and it very well might fix things.

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I've updated my original post to correct an error - it's not actually a 172.17.7.0/24 subnet but rather the same /16 mask, it's just that the Windows Server assigns VPN clients IP from 172.17.7.1 to .240. As you mentioned ARP: I see on my internal host that in his routing table, he has an entry like this: 172.17.7.7 c6:4f:51:a3:48:ec UHLWIi 0 2 en0 1196. I guess that MAC address belongs somehow to the Windows Server, but how can I verify that? ipconfig /all gives me nothing. I'll try your suggestion with the different subnet now. Thanks! –  zakharov May 24 '12 at 9:35
    
Okay, so the VPN clients now get IPs from the 172.18.x.x range. When I added a static route on the router for 172.18.0.0/16 -> 172.17.1.1 pings started to work again, but it didn't change anything for TCP. Any additional info I could provide that might help? Any clue why those DUP ACKs seem to be coming from the internal host? –  zakharov May 24 '12 at 10:26

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