There are few vSphere Infrastructure enterprise possibilities how to deal with this type of attack.
I know about two ... Vmware vShield and CISCO Nexus1000v.
However here I would like to share idea how to do it with open source tools integrated into enterprise infrastructure.
Please be aware that this is not out of box enterprise solution and you have to know what you are doing and you have full responsibility for all impacts.
How we can simulate the attack?
Bellow is tutorial inspired by another tutorial from
You can simply change installation procedures based on your OS distribution.
ARP poisoning with dsniff
dsniff is a collection of tools for network auditing and penetration testing. dsniff, filesnarf, mailsnarf, msgsnarf, urlsnarf, and webspy passively monitor a network for interesting data (passwords, e-mail, files, etc.). arpspoof, dnsspoof, and macof facilitate the interception of network traffic normally unavailable to an attacker (e.g, due to layer-2 switching). sshmitm and webmitm implement active monkey-in-the-middle attacks against redirected SSH and HTTPS sessions by exploiting weak bindings in ad-hoc PKI.
To install dsniff on CentOS 6.
yum -y install wget
rpm -ivh epel-release-6-7.noarch.rpm
yum –y install openssl gcc flex bison libpcap-devel libnet
yum install dsniff
Now you need to find out two things,
1. IP address of the target machine - say 192.168.1.4
2. IP address of the Gateway - say 192.168.1.1
Let's start ARP poisoning from the attacker's machine - with arpspoof tool which comes with dsniff.
$ sudo arpspoof -i en1 -t 192.168.1.4 192.168.1.1
This will update target machine's ARP table with attacker's MAC address against the IP address of the gateway.
Now - start a tcpdump on the same interface from your machine - start viewing all the traffic going to and from the target machine.
$ sudo tcpdump -i en1
How we can detect the attack?
We can use aprwatch for example on my favorite OS FreeBSD running in virtual machine,
Installation is simple as
then you have to add
in to your /etc/rc.conf
And last but not least is to enable promiscuous mode
on VMware vSwitch portgroup where arpwatch vm is connected to. The best way is to create another portgroup (single port is enough) with the same VLAN ID as protected VLAN and in Security we have to set Promiscuous Mode to Accept.
... then arpwatch send message to syslog. So you can see something similar in your /var/log/messages
Oct 31 09:08:02 ips arpwatch: flip flop a.b.c.d 0:50:56:8d:2e:bc (54:52:0:fe:47:95)
Arpwatch can also send a e-mail message about incident. The message looks like
ip address: 220.127.116.11
ethernet address: 54:52:0:fe:47:95
old ethernet address: 0:50:56:8d:2e:bc
old ethernet vendor: VMWare, Inc.
timestamp: Wednesday, October 31, 2012 8:57:33 +0100
previous timestamp: Wednesday, October 31, 2012 8:57:33 +0100
delta: 0 seconds
How we can protect against the attack?
Well this is another story. It really depends on your environment but in my environment I have vSphere Distributed Switch and all virtual machines have VMtools installed so I trust VMware MAC:IP associations and based on these information (MAC) I can find the attacker port in distributed switch and disable it.
And that's just a small step to do it in automated way by leveraging VMware vCLI (aka VMware Perl SDK).
Currently described solution works only on single ESX host and doesn't work among more ESX hosts because of virtual networking principles. VMware virtual switch (or module of distributed switch) is not a switch but port extender. The difference is significant. The ARP poisoning attack is based on permanently unicasting ARP replies to the victim so when Arpwatch server is not on the same ESX as the attacker or the victim then even promiscuous port on distributed switch portgroup will not help us to catch it because arp reply packet is not visible on Arpwatch server.
The solution would be to have arpwatch VM on each ESX host. VMware introduced the concept of ESX agents (aka Agent Virtual Machines) so I believe this is the right use case for ESX agent implementation.
For more information about "Deploying vSphere Solutions, vServices, and ESX Agents" read this document
I have to test this architecture ... so stay tuned.
Any comments or thoughts are appreciated.