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copied!<p><a href="http://msdn.microsoft.com/en-us/library/aa479391.aspx" rel="noreferrer">The article Chris provided as a comment</a> was the solution. </p> <p>What's required is to by-pass Forms Authentication for certain requests and use Basic HTTP Authentication instead. This is then supported by Outlook (and potentially other agents, like web browsers).</p> <p>This is achieved by using the <a href="http://www.raboof.com/projects/madam/" rel="noreferrer">MADAM Http Module</a>.</p> <p>Steps:</p> <p>1> Read the article to gain a basic understanding.</p> <p>2> Install the MADAM NuGet package: <strong>PM> Install-Package madam</strong></p> <p>3> Implement your own <strong>IUserSecurityAuthority</strong>:</p> <p>e.g</p> <pre><code>public class MadamUserSecurityAuthority : IUserSecurityAuthority { public MadamUserSecurityAuthority() { } //This constructor is required public MadamUserSecurityAuthority(IDictionary options) { } public object Authenticate(string userName, object password, PasswordFormat format, IDictionary options, string authenticationType) { if (_yourAuthenticationService.isValid(userName, password.ToString())) return true; //Returning null means the authentication failed return null; } public string RealmName { get { return "MADAM"; } } } </code></pre> <p>4> Add the following to your web config:</p> <p>eg:</p> <pre><code><sectionGroup name="madam"> <section name="userSecurityAuthority" type="System.Configuration.SingleTagSectionHandler, System, Version=1.0.5000.0, Culture=neutral, PublicKeyToken=b77a5c561934e089"/> <section name="formsAuthenticationDisposition" type="Madam.FormsAuthenticationDispositionSectionHandler, Madam"/> </sectionGroup> <madam> <formsAuthenticationDisposition> <discriminators all="true"> <discriminator inputExpression="Request.Url" pattern="Calendar\.aspx" type="Madam.RegexDiscriminator"/> </discriminators> </formsAuthenticationDisposition> <userSecurityAuthority realm="MADAM" provider="YourAppAssembly.MadamUserSecurityAuthority, YourAppAssembly"/> </madam> <httpModules> <add name="FormsAuthenticationDisposition" type="Madam.FormsAuthenticationDispositionModule, Madam"/> <add name="AuthenticationModule" type="Madam.BasicAuthenticationModule, Madam"/> </httpModules> </code></pre> <p><strong>Note 1:</strong> </p> <pre><code><discriminator inputExpression="Request.Url" pattern="Calendar\.aspx" type="Madam.RegexDiscriminator"/> </code></pre> <p>...is used to identify which requests should by-pass forms authentication and use basic HTTP authentication, this is done with Regex, and you can add multiple discriminators.</p> <p><strong>Note 2:</strong></p> <pre><code><userSecurityAuthority realm="MADAM" provider="YourAppAssembly.MadamUserSecurityAuthority, YourAppAssembly"/> </code></pre> <p>....is where you configure your custom authentication provider (i.e. where you check credentials against your DB).</p>

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