The Remote Access VPN Battle — SSL vs IPSec VPN

I’ve recently posted two articles covering two different VPN connection methods. SSL Remote VPN and IPSec Remote VPN via Cisco ASA security applicance. In the article I promised I would go thru and do a deteail compare and contrast of them. So Let’s get start!!

As promised here is the follow up post I mentioned here regarding setting up an Cisco AnyConnect remote access. Luckly the process is very similar to a remote access IPSec tunnel in the previous article with a few exceptions. Lets work through the differences between Cisco AnyConnect and a standard remote access IPSec Client VPN.

Comparison SSL Remote VPN IPSec Remote VPN
Cost $$ per Connection, SSL certificate costs Usually none, no SSL certificate costs
Capacity Seats limited to licensing Limited to Crypto Hardware
Performance SSL with DTLS = Very Fast IPsec without NAT-T = fast
Vulnerability SSL vulnerabilties released frequently IPSec requires pre-shared key
Requirements SSL requires TCP 443, DTLS requires UDP 443 IPSec requires IP Protcol 50 (ESP) and UDP 500(IKEv1), NAT-T requires UDP 4500
Connection Considerations SSL requires TCP 443 outbound for clients IPSec requires both Layer 3 and Layer 4 protocols

NOTE: The table here is a quick reference when comprising SSL remote VPN with IPSec remote VPN. There are many things to consider when choosing between the two. SSL VPN is newer than IPSec, however the answer on which is better is not so straight forward.

IPSec remote VPN utilizes a variety of protocols and ports to form a successful tunnel. If you remember from my article on IPSec and NAT-Traversal, port requirements are UDP 500 for IKEv1 exchange, IP Protocol 50 for ESP communication, and if negotiated UDP 4500 for NAT-T. Most of the time these ports and protocols will not be allowed access outbound to the Internet. For instance, many guest networks like hotels and conferences only allow web browsable ports, such as 80(HTTP) and 443(HTTPS) outbound. That is a lot of firewall exceptions to establish an IPSec remote VPN.

SSL remote VPN introduces many connection and scalability improvements, making remote VPN functionality easier for the end user. SSL remote VPN solves the IPSec issues of a opening ports to establish a VPN session. Remote users no longer connect differently depending on where they are nor do they need to know how they are connected to the Internet, no fancy ports need to be opened, no issues with NAT-Traversal, etc. SSL remote VPN uses a very common trusted port for communication TCP 443 (and UDP 443, more on that later). This port is 99% of the time open to communicate with the Internet web sites. Using a commonly allowed port eliminates the issues seen with IPSec when establishing a VPN.

The trade-off, SSL remote VPN communicates via SSL/TLS. As stated this requires TCP, which is a stateful transport protocol. The issue arises when you have a remote host operating an application that uses TCP as well, such as web browser or Remote Desktop Connection. The scenario is now TCP on top of TCP, resulting in heavy overhead. Imaging the following scenario, you have a SSL remote VPN host connected, they then open a RDP session to a server on your network. So far so good. Now what happens when either the RDP session or the SSL remote VPN session requires a re-transmission because of connectivity problems. TCP re-transmission storms. Both the VPN session and RDP session will require re-transmissions, generating heavy overhead. Now this is not to say that either session will not recover, cause they will unless the connection is completely severed, TCP will do its job. Datagram Transport Layer Security(DTLS) to the rescue!!!

Datagram Transport Layer Security (DTLS)

DTLS is the savior and its what makes SSL client VPNs a very competitive remote access VPN technology. DTLS was designed to secure traffic similar to TLS, but without having to rely so heavily on the underlying TCP transport. TLS relies on TCP to guarantee delivery in the event of message fragmentation, message reordering, and message loss. So getting ride of any one of those TCP features will break the TLS crypto logic.  DTLS solution to these issues is as follows:

  • Message Fragmentation — Fragmentation occurs when a packet datagram is too large to fit within an MTU (usually 1500bytes’ish). Fragmentation is detected and handled by the transport technology (TCP/UDP). TCP has mechanisms built in to solve this while UDP does not. DTLS solves this issue by introducing its own fragmentation offset and length value in the DTLS message itself. This ensure that both ends of the communication are provided fragmentation information regardless of the underlying transport.
  • Message Reordering — Reordering occurs for several reasons, a common reason is delayed delivery of the underlying network. Reordering isn’t a huge issue for transport technologies like TCP because it uses sequence numbering to ensure the original data is reassembled properly. TLS requires the sequential delivery of packets to preform it’s crypto logic, meaning TLS needs the previous packet to be able to decrypt the next packet N+1. DTLS solves this by adding it’s own sequence numbering to the application, allowing it to not be dependent on the underlying transport technology.
  • Message Loss — Packet loss occurs when a packet in a data stream never reaches its destination in a certain period of time. Message loss is handled very similar to Message Recording. For TLS and it’s TCP transport, re-transmissions are triggered for lost packets when sequence numbering doesn’t compute correctly for a agreed upon window. DTLS fixes this by adding a simple re-transmission timer to it’s application logic, thereby allowing it to re-transmit packets without relying on the transport protocol.

Keep in mind that DTLS built-in functionality of these usually transport specific recovery mechanisms creates the need for additional RAM/memory on the server-side. Another cool fact is most of these “fixes” come from IPSec ESP technology! See RFC4347 for more information.

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