Hardening web apps: 3. Authentication

This third post in the blog series goes into detail about authenticating users but first, let’s agree there is no sane way of implementing authentication without an underlying transport encryption.

Transport security

Because of man-in-the-middle attacks, any information transmitted over the internet without using strong encryption you can safely assume is public knowledge. Some would argue that is also the case for data transmitted on an enterprise corporate LAN.

Basically to enable transport security you need a certificate authority that you clients’ browsers trust to issue a public/private key pair in form of a certificate. The private key is kept secret on your front end web servers and used for decrypting an incoming request and encrypting the response by adding an SSL layer on top of HTTP. Instead of using port 80 HTTPS defaults to port 443.

It is best practice to have a short SSL certificate lifetime to minimize damage should a certificate be exposed without your knowledge. For example, certificates issued by the LetsEncrypt initiative have 90 days’ lifetime to encourage automated certificate renewal. However, these tools are not yet ported to IIS. If you just need standard domain validated certificates go with 1 year certificates from any cheap certificate authority. Besides domain validated (DV) certificates, that basically tells your users the can trust you have some sort of control over the internet domain name, there are also organization validated (OV) and extended validation (EV) certificates. Forget about OV, and purchase the quite expensive EV only if your users require that you prove your legal entity.

The excellent online Qualsys SSL Server Test will check your HTTPS configuration for weaknesses and score it accordingly. Unless you really need to support legacy WinXP there is no reason to go for less than an A. Retest your configuration periodically as holes in cryptography are commonly discovered. In reality several classes of cryptography that was thought to be secure a year ago are now completely useless.


Web apps usually need to have some sort of way to identify its users e.g. to restrict access to a partitions of persisted data. 

Legacy systems on corporate LANs would traditionally simply use integrated Windows authentication (IWA), however it will not work over the internet or from small devices. Another classic, form based authentication (FBA) is still a fair choice for really simple scenarios.

For maximum flexibility use OpenID Connect. That will enable your users to sign in using their existing Facebook, Google, Microsoft or whatever account, and you will not have to deal with storing passwords, let alone support forgotten passwords scenarios.

Do not try to design, or let alone implement your own magic cryptography or user authentication. Writing security libraries is extremely hard, and unless you are in the security library business go and reference a good battle proven open source component instead, e.g. the OWIN middleware.

Always generate secrets using a strong random number generator (i.e. from the System.Security.Cryptography namespace). Let me explicitly mention that System.Guid or System.Random was never meant for this level of randomness and should not be used for secrets.

Microsoft currently have Azure AD B2C in preview. Built on Azure AD that handles billions of sign-ins per day, but targeted towards consumers it looks promising with advanced features like multi factor authentication, however still in preview and has some shortcomings.

Read the next post in the blog series about mitigating cross site attacks.