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Have Site-To-Site (IPSEC) connected but cannot ping anything other than router

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Just setup a new Azure subscription, and i'm stumped trying to troubleshoot why I can't ping any local VMWare machines from a Azure VM. After successfully setting up an IPSec Site-To-Site VPN.

I am doing this as a learning exercise to setup a home lab, and working on my crappy networking skills :(

I have the following setup:

• Esxi Server with a VM (Portal) on a vlan50 network


• Managed switch with vlan50 tagging


• pfSense router with 192.168.20.1/24 address on vlan50


• A working IPSec tunnel from my lab 192.168.20.0/24 to Azure
  virtual network 192.168.50.0/24
  

So for testing I created 1 VM in on-prem lab, and 1 VM in Azure

• On-prem VM [Portal] - 192.168.20.2 vlan50
  


• Azure VM [TestVM] - 192.168.50.100 (no vlan)
  

From the Portal Server, I can ping the local gateway 192.168.20.1,

And from the pfSense I can ping the Azure VM:

Ping from pfSense to AzureVM

And from the Azure Server, I can ping the 192.168.20.1 interface.

Ping from Azure to pfSense interface, not enough reputation :(

However, the VMs cannot see each otherping each other. I cannot understand this. I added rules in both IPSec & the vlan50 to allow all access to each subnet. I have a feeling my issue is either a Firewall rule, or vlan tag?

Here are some interesting things I'm noticing while troubleshooting:

1. I don't see any ICMP traffic on the vlan50 interface when successfully pinging from pfSense to AzureVM


2. When (unsuccessfully) pinging from AzureVM to Portal box, I see unanswered ICMP requests from 192.168.50.100 when listening on pfSense box on the vlan50 interface

I also created a very crude network outline with screenshots of the configuration I have setup: Crude Network layout

vpn vlan azure ipsec pfsense

share|improve this question

edited Feb 27 '16 at 20:47

The Unique Paul Smith

asked Feb 27 '16 at 20:42

The Unique Paul SmithThe Unique Paul Smith

10616

bumped to the homepage by Community♦ 21 hours ago

This question has answers that may be good or bad; the system has marked it active so that they can be reviewed.

add a comment | 

1

Just setup a new Azure subscription, and i'm stumped trying to troubleshoot why I can't ping any local VMWare machines from a Azure VM. After successfully setting up an IPSec Site-To-Site VPN.

I am doing this as a learning exercise to setup a home lab, and working on my crappy networking skills :(

I have the following setup:

• Esxi Server with a VM (Portal) on a vlan50 network


• Managed switch with vlan50 tagging


• pfSense router with 192.168.20.1/24 address on vlan50


• A working IPSec tunnel from my lab 192.168.20.0/24 to Azure
  virtual network 192.168.50.0/24
  

So for testing I created 1 VM in on-prem lab, and 1 VM in Azure

• On-prem VM [Portal] - 192.168.20.2 vlan50
  


• Azure VM [TestVM] - 192.168.50.100 (no vlan)
  

From the Portal Server, I can ping the local gateway 192.168.20.1,

And from the pfSense I can ping the Azure VM:

Ping from pfSense to AzureVM

And from the Azure Server, I can ping the 192.168.20.1 interface.

Ping from Azure to pfSense interface, not enough reputation :(

However, the VMs cannot see each otherping each other. I cannot understand this. I added rules in both IPSec & the vlan50 to allow all access to each subnet. I have a feeling my issue is either a Firewall rule, or vlan tag?

Here are some interesting things I'm noticing while troubleshooting:

1. I don't see any ICMP traffic on the vlan50 interface when successfully pinging from pfSense to AzureVM


2. When (unsuccessfully) pinging from AzureVM to Portal box, I see unanswered ICMP requests from 192.168.50.100 when listening on pfSense box on the vlan50 interface

I also created a very crude network outline with screenshots of the configuration I have setup: Crude Network layout

vpn vlan azure ipsec pfsense

share|improve this question

edited Feb 27 '16 at 20:47

The Unique Paul Smith

asked Feb 27 '16 at 20:42

The Unique Paul SmithThe Unique Paul Smith

10616

bumped to the homepage by Community♦ 21 hours ago

This question has answers that may be good or bad; the system has marked it active so that they can be reviewed.

add a comment | 

Just setup a new Azure subscription, and i'm stumped trying to troubleshoot why I can't ping any local VMWare machines from a Azure VM. After successfully setting up an IPSec Site-To-Site VPN.

I am doing this as a learning exercise to setup a home lab, and working on my crappy networking skills :(

I have the following setup:

• Esxi Server with a VM (Portal) on a vlan50 network


• Managed switch with vlan50 tagging


• pfSense router with 192.168.20.1/24 address on vlan50


• A working IPSec tunnel from my lab 192.168.20.0/24 to Azure
  virtual network 192.168.50.0/24
  

So for testing I created 1 VM in on-prem lab, and 1 VM in Azure

• On-prem VM [Portal] - 192.168.20.2 vlan50
  


• Azure VM [TestVM] - 192.168.50.100 (no vlan)
  

From the Portal Server, I can ping the local gateway 192.168.20.1,

And from the pfSense I can ping the Azure VM:

Ping from pfSense to AzureVM

And from the Azure Server, I can ping the 192.168.20.1 interface.

Ping from Azure to pfSense interface, not enough reputation :(

However, the VMs cannot see each otherping each other. I cannot understand this. I added rules in both IPSec & the vlan50 to allow all access to each subnet. I have a feeling my issue is either a Firewall rule, or vlan tag?

Here are some interesting things I'm noticing while troubleshooting:

1. I don't see any ICMP traffic on the vlan50 interface when successfully pinging from pfSense to AzureVM


2. When (unsuccessfully) pinging from AzureVM to Portal box, I see unanswered ICMP requests from 192.168.50.100 when listening on pfSense box on the vlan50 interface

I also created a very crude network outline with screenshots of the configuration I have setup: Crude Network layout

vpn vlan azure ipsec pfsense

share|improve this question

edited Feb 27 '16 at 20:47

The Unique Paul Smith

asked Feb 27 '16 at 20:42

The Unique Paul SmithThe Unique Paul Smith

10616

share|improve this question

edited Feb 27 '16 at 20:47

The Unique Paul Smith

asked Feb 27 '16 at 20:42

The Unique Paul SmithThe Unique Paul Smith

10616

share|improve this question

edited Feb 27 '16 at 20:47

The Unique Paul Smith

asked Feb 27 '16 at 20:42

The Unique Paul SmithThe Unique Paul Smith

10616

asked Feb 27 '16 at 20:42

The Unique Paul SmithThe Unique Paul Smith

10616

asked Feb 27 '16 at 20:42

The Unique Paul SmithThe Unique Paul Smith

10616

1 Answer
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0

Doh! I found the answer was the fact that my Portal machine that's on-premise has multiple NIC, and the default Gateway doesn't know that route. I added a static gateway and was able to successfully ping each machine

share|improve this answer

answered Mar 30 '16 at 2:31

The Unique Paul SmithThe Unique Paul Smith

10616

add a comment | 

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0

Doh! I found the answer was the fact that my Portal machine that's on-premise has multiple NIC, and the default Gateway doesn't know that route. I added a static gateway and was able to successfully ping each machine

share|improve this answer

answered Mar 30 '16 at 2:31

The Unique Paul SmithThe Unique Paul Smith

10616

add a comment | 

0

Doh! I found the answer was the fact that my Portal machine that's on-premise has multiple NIC, and the default Gateway doesn't know that route. I added a static gateway and was able to successfully ping each machine

share|improve this answer

answered Mar 30 '16 at 2:31

The Unique Paul SmithThe Unique Paul Smith

10616

add a comment | 

Doh! I found the answer was the fact that my Portal machine that's on-premise has multiple NIC, and the default Gateway doesn't know that route. I added a static gateway and was able to successfully ping each machine

share|improve this answer

answered Mar 30 '16 at 2:31

The Unique Paul SmithThe Unique Paul Smith

10616

share|improve this answer

answered Mar 30 '16 at 2:31

The Unique Paul SmithThe Unique Paul Smith

10616

answered Mar 30 '16 at 2:31

The Unique Paul SmithThe Unique Paul Smith

10616

answered Mar 30 '16 at 2:31

The Unique Paul SmithThe Unique Paul Smith

10616