Secure Socket Tunneling Protocol

The article will give a clear understanding of SSTP and compare standard VPN vs SSTP VPN. The article will also cover the advantages of utilizing both SSTP and VPN simultaneously and what the benefits of using SSTP will be.


Virtual private network, also referred to as VPN, is a network that is constructed with the use of public wires to join nodes, enabling the user to create networks for the transfer of data. The systems use encryption and various other security measures to ensure that the data is not intercepted by unauthorized users. For years VPN has been used successfully but has recently become problematic due to the increase in the number of organizations encouraging roaming user access. Alternative measures have been looked at to enable this type of access. Many organizations have begun to utilize IPSec and SSL VPN as an alternative. The other new alternative being SSTP, also referred to as ‘Microsoft’s SSL VPN’.

Problems with typical VPN

VPNs typically use an encrypted tunnel that keeps the tunneled data confidential. By doing this when the tunnel routes through typical NATed paths the VPN tunnel stops working. VPNs typically connect a node to an endpoint. It may happen that both the node and the endpoint have the same internal LAN address and, if NAT is involved, all sorts of complications can arise.


Secure Socket Layer, also referred to as SSL, uses a cryptographic system that uses two keys to encrypt data, the public and private key. The public key is known to everyone and the private only to the recipient. Through this SSL a secure connection between a client and a server is created. SSL VPN allows users to establish secure remote-access from virtually any internet connected web browser, unlike with VPN. The hurdle of unstable connectivity is removed. With SSL VPN an entire session is secured, whereas with only SSL this is not accomplished.


Secure socket tunneling protocol, also referred to as SSTP, is by definition an application-layer protocol. It is designed to employ a synchronous communication in a back and forth motion between two programs. It allows many application endpoints over one network connection, between peer nodes, thereby enabling efficient usage of the communication resources that are available to that network.

SSTP protocol is based on SSL instead of PPTP or IPSec and uses TCP Port 443 for relaying SSTP traffic. Although it is closely related to SSL, a direct comparison can not be made between SSL and SSTP as SSTP is only a tunneling protocol unlike SSL. Many reasons exist for choosing SSL and not IPSec as the basis for SSTP. IPSec is directed at supporting site- to-site VPN connectivity and thus SSL was a better base for SSTP development, as it supports roaming. Other reasons for not basing it on IPSec are:

  • It does not force strong authentication,

  • User clients are a must have,

  • Differences exist in the quality and coding of user clients from vendor to vendor,

  • Non-IP protocols are not supported by default,

  • Because IPSec was developed for site to site secure connections, it is likely to present problems for remote users attempting to connect from a location with a limited number of IP addresses.

SSL VPN proved to be a more compatible basis for the development of SSTP

SSL VPN addresses these issues and more. Unlike basic SSL, SSL VPN secures an entire session. No static IPs are required, and a client is unnecessary in most cases. Since connections are made via a browser over the Internet, the default connection protocol is TCP/IP. Clients connecting via SSL VPN can be presented with a desktop for accessing network resources. Transparent to the user, traffic from their laptop can be restricted to specific resources based on business defined criteria.

SSTP – an extension of VPN

The development of SSTP was brought about by the lack of capability of VPN. The main shortcoming of VPN is its unstable connectivity. This is a consequence of its insufficient coverage areas. SSTP increases the coverage area of VPN connection ubiquitously, rendering this problem no more. SSTP establishes a connection over secure HTTPS; this allows clients to securely access networks behind NAT routers, firewalls and web proxies, without the concern for typical port blocking issues.

SSTP is not designed for site to site VPN connections but is intended to be used for client to site VPN connections.

The success of SSTP can be found in the following features:

  • SSTP uses HTTPS to establish a secure connection

    • The SSTP (VPN) tunnel will function over Secure-HTTP. The problems with VPN connections based on the Point-to-Point Tunneling Protocol (PPTP) or Layer 2 Tunneling Protocol (L2TP) will be eliminated. Web proxies, firewalls and Network Address Translation (NAT) routers located on the path between clients and servers will no longer block VPN connections.

  • Typical port blocking is decreased

    • Blocking issues involving connections in relation to PPTP GRE port blocking or L2TP ESP port blocking via a firewall or NAT router preventing the client from reaching the server will no longer be a problem as ubiquitous connectivity is achieved. Clients will be able to connect from anywhere on the internet.

  • SSTP will be built into Longhorn server

  • SSTP Client will be built into Windows Vista SP1

    • SSTP won’t require retraining issues as the end-user VPN controls remain unchanged. The SSTP based VPN tunnel plugs directly into current interfaces for Microsoft VPN client and server software.

  • Full support for IPv6. SSTP VPN tunnel can be established across IPv6 internet.

  • It uses integrated network access protection support for client health-check.

  • Strong integration into MS RRAS client and server, with two factor authentication capabilities.

  • Increases the VPN coverage from just a few points to almost any internet connection.

  • SSL encapsulation for traversal over port 443.

  • Can be controlled and managed using application layer firewalls like ISA server.

  • Full network VPN solution, not just an application tunnel for one application.

  • Integration in NAP.

  • Policy integration and configuration possible to help with client health checks.

  • Single session created for the SSL tunnel.

  • Application independent.

  • Stronger forced authentication than IPSec

  • Support for non IP protocols, this is a major improvement over IPSec.

  • No need to buy expensive, hard to configure hardware firewalls that do not support Active directory integration and integrated two factor authentication.

Figure 1.1: The SSTP connection mechanism

How SSTP based VPN connection works in seven steps

  1. The SSTP client needs internet connectivity. Once this internet connectivity is verified by the protocol, a TCP connection is established to the server on port 443.
  2. SSL negotiation now takes place on top of the already established TCP connection whereby the server certificate is validated. If the certificate is valid, the connection is established, if not the connection is torn down.
  3. The client sends an HTTPS request on top of the encrypted SSL session to the server.
  4. The client now sends SSTP control packets within the HTTPS session. This in turn establishes the SSTP state machine on both sides for control purposes, both sides now intiate the PPP layer communication.
  5. PPP negotiation using SSTP over HTTPS now takes place at both ends. The client is now required to authenticate to the server.
  6. The session now binds to the IP interface on both sides and an IP address assigned for routing of traffic.
  7. Traffic can now traverse the connection being either IP traffic or otherwise.

Microsoft is confident that this protocol will help alleviate VPN connection issues, The RRAS team are now readying RRAS for SSTP integration and the protocol will be part of the solution going forward. The only prerequisite at present is that the client runs Vista and Longhorn server. The feature set provided by this little protocol is both rich and flexible and the protocol will enhance the user and administrator experience. I predict that devices will start to incorporate this protocol into the stack for secure communication and the headaches of NAT will soon be forgotten as we move into a 443/SSL incorporated solution.


SSTP is a great addition to the VPN toolkit to enable users to remotely and securely connect to the corporate network. Blocking of remote access and NAT issues seem to be forgotten when using this protocol and the technology is stable, well documented and working. This is a great product and it is very welcome in this time of remote access.

1 thought on “Secure Socket Tunneling Protocol”

  1. Hi Ricky,

    we already to configure SSTP over HTTPS, but have some problem that
    cannot access the sharing folder.

    Is there any port should we to open from public beside HTTPS ?

    Thank’s for your help.

    Warm Regards,

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