+1  A: 

After thinking about what was going on and realizing that issue probably had something to do with NHibernate I refined some of my Google searches and found a post HttpModule and HttpHandler sections in IIS 7 web.config files. This reminded me that NHibernate requires an httpModules entry.

<system.web>
  <httpModules>
    <add name="StartupModule" type="Infrastructure.NHibernateModule,
         Infrastructure, Version=1.0.0.0, Culture=neutral"/>
  </httpModules>
</system.web>

Because of the way that IIS 7 in integrated mode works I had to add the following to the modules section of system.webServer.

<system.webServer>
  <validation validateIntegratedModeConfiguration="false"/>
  <modules runAllManagedModulesForAllRequests="true">
    <add name="StartupModule" type="Infrastructure.NHibernateModule,
         Infrastructure, Version=1.0.0.0, Culture=neutral" />
  </modules>
</system.webServer>

Because I needed to have both the modules work in both system.web and system.webServer I added the validation section to the system.webServer.

ahsteele