Branch Office Connections – GRE over IPSec VPN

While studying for the CCNP Route exam, I noticed that GRE Tunneling and IPSec were mentioned as topics, however configuration of the two was never really covered in the certification guide.  In addition, I did not see any labs involving this type of scenario, so I decided to create my own.  Hopefully this provides some insight to others about how to configure GRE Tunnels over IPsec.  Don’t feel bad if this takes you a while, setting up this scenario and writing this up took a whole Saturday afternoon.  The configuration files are at the bottom of the post.

IPSec can secure data in transit and provides authentication that it came from a trusted source.

To route from the branch office to the enterprise core, you can use either static routes or a routing protocol. To secure traffic over the internet, IPSec can be used.  To utilize a routing protocol to connect securely to the core with IPsec, it must be combined with a GRE tunnel which supports the broadcasts/multicasts necessary for proper IGP operation.

GRE Tunnels

  • Act link a point-to-point link from a Layer 3 perspective.
  • Supports many passenger protocols, including IPv4.
  • Encapsulates/forwards broadcasts and multicasts, therefore supporting IPv4 IGP’s.
  • GRE tunnels can run through IPsec tunnels.

Implementing Branch Office GRE over IPSec VPN

Branch Office GRE/IPSec VPN (R2-R4) & Private Serial (R3-R4)

Here, we will utilize split-tunnel at the Branch Office to ensure that only traffic destined for the Core will be encrypted over the GRE IPSec tunnel. A default route is configured on R2 and R4 to ISP1. Additionally, ISP1 has been configured with a loopback to test split-tunnel functionality.

All routers (except ISP1 obviously) will participate in EIGRP AS 1. Each participating router shall be configured with the network and no auto-summary commands.

Configure the GRE Tunnels on R2 and R4

The tunnel source is the internet-facing interface, in this case fa0/0 with the IP of on R2 and fa0/1 with the IP of on R4.
When associating a tunnel source with an interface, if the associated interface goes down, so does the tunnel.  If you have redundant connections, use a loopback as a source instead.

R2 – R4 GRE Tunnel Configuration

First, configure the GRE tunnel. After doing this, you should see your EIGRP neighbors go up.

In a real world situation, you’d probably also want to configure the tunnel with Path MTU Detection.  This will mitigate fragmentation issues that could cause your routers to drop CEF and use process switching.  Enable PMTUD at each tunnel endpoint with tunnel path-mtu-discovery.



R2 GRE Route-Map

Here, we will configure a route-map to prevent a default route from ever being advertised over the GRE tunnel. The only way for R4 to ever learn R2’s default route should be via the serial connection to R3, and it should only be utilized if R4’s fa0/0 interface goes down. We could also utilize this to block other networks from being advertised over the GRE tunnel by modifying the ACL.

Now, you can see that R4 only learns a backup Default-Route through R3. Previously, it learned it through the tunnel as well, which would be silly to utilize and might break split-tunnel if the static default-route was lost for some reason.

Encrypt GRE Tunnel traffic using IPSec

We will now encrypt traffic traversing the GRE tunnel using IPsec. We must first define an ACL to catch the traffic we wish to encrypt, which will be GRE traffic from our GRE source-interface destined for the GRE tunnel destination.

R2 IPsec Policy Creation

ACL (Catch GRE to R4)


ISAKMP Key & IPSec Transform Set (Transport Mode)

Keep in mind that transport mode is used only because we are not traversing NAT, we are going from R2 to R4’s public IP for both IPSec and GRE Tunnels.   Tunnel mode is required if the GRE destination is different from the IPSec destination.  If the endpoints were each behind a NAT router, the situation requires a combination of NAT-T and Tunnel Mode.  Tunnel mode adds an extra 20 bytes to the overall packet size. NAT-T also adds an extra 20 bytes per packet and encapsulates the IPSec traffic into UDP packets over port 4500.

Crypto Map Configuration

Here, we configure the Crypto Map to R4. We will use the previously created GRE catching ACL.

Apply Crypto Map to GRE Tunnel

The Crypto Map should be applied to the physical exit interface. Cisco recommends applying it to the logical tunnel interface as well.

R4 IPsec Policy Creation

We will follow the same procedure utilized on R2 and reverse the IP addresses.

ACL (Catch GRE to R2)


ISAKMP Key & IPSec Transform Set (Transport Mode)

Crypto Map Configuration

Here, we configure the Crypto Map to R4. We will use the previously created GRE catching ACL.

Apply Crypto Map to GRE Tunnel

Verify IPsec and Split-Tunnel Functionality

You can utilize Wireshark to verify only ESP traffic traverses between the GRE endpoints. I found that the Crypto Map did not need to be applied to the logical Tunnel 0 interface to function, but only the physical exit interface. I am not sure why Cisco recommends applying it to both.

You can see that the Crypto traffic for Tunnel 0 and FastEthernet 0/0 is identical. I am not sure if running the crypto map VPN on both the Tunnel 0 and FastEthernet 0/0 is causing excess encryption overhead, or if it only encrypts the traffic once.

After disabling Crypto Map VPN on the Tunnel 0 interface, I confirmed via Wireshark that the GRE traffic continued to be encrypted. A show crypto ipsec sa detail shows that the traffic continues to be encrypted as well.

Verify Split-Tunnel

To test this, I will simply ping a simulated public internet address of from the inside interface of R4.


We have implemented remote branch office with redundant connectivity to the core; a leased line and a secured backup utilizing GRE over IPsec via the public Internet. Our branch office is now able to participate in the EIGRP routing process over either link.  If you wanted to use the IPsec VPN as your primary connection to HQ, modify the bandwidth value of the Tunnel 0 interfaces to make the EIGRP metric more preferable than the serial route.  By default, tunnel interfaces seem to be given a bandwidth value of only 9kbps.  The default delay value of tunnel interfaces is high as well.  Tweak the bandwidth and delay values to achieve desired results.

Normal Conditions

Downed Serial Link to HQ

Configuration Files

ISP1 Configuration

R1 Configuration

R2 Configuration

R3 Configuration

R4 Configuration


3 thoughts on “Branch Office Connections – GRE over IPSec VPN

  1. Nice post!! Took me a while to parse through, especially since I don’t know much about security yet; I’m working on ROUTE right now.

    I downloaded R4’s config to see the NAT setup (getting the order of what happens when takes some thinking) and I noticed that you have PBR set up on tun0 referencing GRE_BLOCK. From what I understand this will effectively block any source traffic going towards the tunnel with a source IP address of Is this intentional, and if so, why is it there?

    Again, awesome post, and thank you for spending the time writing about it!


    1. Hi Yosef. I am glad you found my post useful! This is some seriously complicated stuff and I knew I’d forget it if I didn’t write it down… It’s a good habit to get into and I suggest Microsoft OneNote if you don’t use it already.

      Anyway, I believe that the purpose of the route map is to prevent R4 from ever learning a default route through R2 or vice versa over the GRE Tunnel. This is because the GRE IPSec tunnel leverages a connection through the ISP to connect R2 to R4. Therefore R2 should never use a default route through R4 over the tunnel since the ISP is ultimately the default route of both routers. R2 and R4 are dependent upon their default route to establish the tunnel therefore if the tunnel is up it is implied that the DG(ISP) is up and the ISP is the only egress point for bother sides on the network… You wouldn’t want to route traffic from R2 to R4 via ISP if R4 is simply going to send it right back to ISP. If there was a second ISP at the main site then maybe we might consider lifting that block… It is there purely as a preventative measure. I wrote a paragraph about that in the post though just use a search on the page for GRE_BLOCK. Ultimately, the Route Map (PBR) prevents only the default route ( from being learned over the tunnel; any other more specific route will be permitted.

      If you need further explanation I will try to help! It is simply a topic difficult to explain without being face to face with a white board. Good luck on your CCNP journey and be sure to document this stuff… It is great material to refresh your memory!

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