Since Elmah is open source, you should add the code as a project in your solution and make sure that you have visual studio break on all exceptions. It sounds feasible that Elmah is throwing an Exception which would be swallowed. This exact thing was happening with me and it was a permission on the stored procedure that inserts the error.
ORIGINAL
Is your test within a try/catch block? If so, you'll have to explicitly force the logging to occur.
Elmah.ErrorSignal.FromCurrentContext().Raise(ex);
MY WEB.CONFIG SETUP
<configSections>
<sectionGroup name="elmah">
<section name="security" type="Elmah.SecuritySectionHandler, Elmah"/>
<section name="errorLog" type="Elmah.ErrorLogSectionHandler, Elmah" />
<section name="errorMail" type="Elmah.ErrorMailSectionHandler, Elmah" />
<section name="errorFilter" type="Elmah.ErrorFilterSectionHandler, Elmah"/>
</sectionGroup>
...
</configSections>
<elmah>
<security allowRemoteAccess="0" />
<errorLog type="Elmah.SqlErrorLog, Elmah" connectionStringName="TESTElmahConnectionString" />
<errorFilter>
<test>
<equal binding="HttpStatusCode" value="404" type="Int32" />
</test>
</errorFilter>
</elmah>
<httpModules>
<add name="ErrorLog" type="Elmah.ErrorLogModule, Elmah"/>
<add name="ErrorMail" type="Elmah.ErrorMailModule, Elmah"/>
<add name="ErrorFilter" type="Elmah.ErrorFilterModule, Elmah"/>
<add name="ScriptModule" type="System.Web.Handlers.ScriptModule, System.Web.Extensions, Version=3.5.0.0, Culture=neutral, PublicKeyToken=31BF3856AD364E35"/>
</httpModules>
<system.webServer>
<validation validateIntegratedModeConfiguration="false"/>
<modules>
<remove name="ScriptModule"/>
<add name="ScriptModule" preCondition="managedHandler" type="System.Web.Handlers.ScriptModule, System.Web.Extensions, Version=3.5.0.0, Culture=neutral, PublicKeyToken=31BF3856AD364E35"/>
<add name="ErrorLog" type="Elmah.ErrorLogModule, Elmah" preCondition="managedHandler" />
<add name="ErrorFilter" type="Elmah.ErrorFilterModule, Elmah" preCondition="managedHandler" />
<add name="ErrorMail" type="Elmah.ErrorMailModule, Elmah" preCondition="managedHandler" />
</modules>
<handlers>
<remove name="WebServiceHandlerFactory-Integrated"/>
<remove name="ScriptHandlerFactory"/>
<remove name="ScriptHandlerFactoryAppServices"/>
<remove name="ScriptResource"/>
<add name="ScriptHandlerFactory" verb="*" path="*.asmx" preCondition="integratedMode" type="System.Web.Script.Services.ScriptHandlerFactory, System.Web.Extensions, Version=3.5.0.0, Culture=neutral, PublicKeyToken=31BF3856AD364E35"/>
<add name="ScriptHandlerFactoryAppServices" verb="*" path="*_AppService.axd" preCondition="integratedMode" type="System.Web.Script.Services.ScriptHandlerFactory, System.Web.Extensions, Version=3.5.0.0, Culture=neutral, PublicKeyToken=31BF3856AD364E35"/>
<add name="ScriptResource" preCondition="integratedMode" verb="GET,HEAD" path="ScriptResource.axd" type="System.Web.Handlers.ScriptResourceHandler, System.Web.Extensions, Version=3.5.0.0, Culture=neutral, PublicKeyToken=31BF3856AD364E35"/>
</handlers>
</system.webServer>