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VPNs with SSTP<br />

Nuts and Bolts<br />

Figure 4: You need to set up the RAS services to run a VPN server.<br />

Microsoft’s SSTP encapsulation structure<br />

is like a Russian doll. Just as<br />

with PPTP, Microsoft uses the PPP<br />

protocol with SSTP, which leads to a<br />

fairly complex encapsulation structure<br />

(see Figure 6), in which an IP header<br />

contains a TCP header, which in turn<br />

contains an SSTP header, which then<br />

contains a PPP header, which finally<br />

contains the IP packets themselves.<br />

Although the method seems to be<br />

slightly more efficient than Encapsulating<br />

Security Payload (ESP), with<br />

an overhead of 8 bytes in the PPP<br />

header, compared with 20 bytes in<br />

IPsec over HTTPS, there is actually no<br />

real need to encapsulate in PPP packthe<br />

Customize this server section of<br />

the Server Manager, the Routing and<br />

Remote Access tool is available below<br />

Management. The Action | Configure<br />

and enable routing and RAS button<br />

takes you to the Routing and Remote<br />

Access Server Setup Wizard.<br />

At the second Configuration step<br />

(Figure 4), you’ll want to enable<br />

Virtual private network (VPN) access<br />

and NAT, then click Next and select<br />

the required network interface. At the<br />

following step, Address assignment<br />

defines how the VPN server assigns<br />

IP addresses to remote clients. If you<br />

have the DHCP service running, Automatic<br />

is the quickest and cleanest<br />

option. Then you can define an IP<br />

address pool for the DHCP server to<br />

use in the next step, Address range<br />

assignment.<br />

In the final step, you can choose<br />

whether or not to use a Radius server<br />

to authenticate clients on a large-scale<br />

network; this is disabled by default.<br />

The wizard will then instruct you to<br />

set up the DHCP relay agent for Windows<br />

to support the forwarding of<br />

DHCP messages<br />

to RAS clients.<br />

To do this, you<br />

need to enable<br />

the Relay DHCP<br />

packets option in<br />

the DHCP Relay Properties dialog box<br />

(Figure 5).<br />

Conclusions<br />

IPv4 or IPv6 TCP SSTP PPP IPv4 or IPv6 packet<br />

Encapsulated SSL session<br />

Figure 6: The SSTP encapsulation structure is like a Russian doll. Microsoft has gone to considerable trouble<br />

to make something proprietary from what are basically open protocols. From a technical point of view, there<br />

seems to be no real reason to use PPP.<br />

Figure 5: Configuring Windows to forward DHCP messages to the RAS clients.<br />

ets. In IPsec, ESP builds directly on<br />

IP. Microsoft is quite obviously seeking<br />

to set itself apart by encapsulating<br />

in PPP.<br />

Apart from the fairly complex Windows<br />

server configuration, which<br />

mainly involves setting up the certificate<br />

services, and possibly packet<br />

filters for transporting the certificate<br />

requests, SSTP offers a secure, wellperforming<br />

tunnel technology for the<br />

future.<br />

n<br />

Info<br />

[1] Microsoft support for SSTP: [http://​<br />

support. microsoft. com/ kb/ 947032/]<br />

[2] TMG 2010: [http:// www. microsoft. com/​<br />

downloads/ details. aspx? familyid=e05a<br />

ecbc‐d0eb‐4e0f‐a5db‐8f236995bccd&​<br />

displaylang=en]<br />

The Author<br />

Thomas Drilling has been a freelance journalist<br />

and editor for scientific and IT magazines for<br />

more than 10 years. With his editorial office<br />

team, he regularly writes on the subject of open<br />

source, Linux, servers, IT administration, and<br />

Mac OS X. In addition to this, Thomas Drilling is<br />

also a book author and publisher, a consultant<br />

to small and medium-sized companies, and a<br />

regular speaker on Linux, open source, and IT<br />

security.<br />

www.admin-magazine.com<br />

Admin 01<br />

97

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