Why is my ClaimsIdentity IsAuthenticated always false (for web api Authorize filter)?

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The problem is because of a breaking change in .Net 4.5. As explained by this article, simply constructing a claims identity no longer makes it IsAuthenticated return true. Instead, you need to pass some string (doesn’t matter what) into the constructor.

So this line in the above code:

var claimsIdentity = new ClaimsIdentity( claims );

Becomes this:

// exact string doesn't matter
var claimsIdentity = new ClaimsIdentity( claims, "CustomApiKeyAuth" );

And the problem is solved. Update: see other answer from Leo. The exact AuthenticationType value may or may not be important depending on what else you have in your auth pipeline.

Update 2: as suggested by Robin van der Knaap in the comments, one of the System.Security.Claims.AuthenticationTypes values might be appropriate. 

var claimsIdentity = new ClaimsIdentity( claims, AuthenticationTypes.Password );

// and elsewhere in your application...
if (User.Identity.AuthenticationType == AuthenticationTypes.Password) {
    // ...
}

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