If you enter the following web.config appSettings settings, it should spring to life:
<add key="owin:AutomaticAppStartup" value="true" />
<add key="owin:appStartup" value="UmbracoDefaultOwinStartup" />
I got this error after updating 7.2.8 → 7.4.1. After doing the above, Umbraco stated that it could not find System.Object. This was allowed by adding the following section to the assembly:
<add assembly="System.Runtime, Version=4.0.0.0, Culture=neutral, PublicKeyToken=b03f5f7f11d50a3a" />
; - ( , "umbraco" Microsoft.Owin 2.1.0, Umbraco NuGet 3.0.1.0), assemblyBinding:
<dependentAssembly>
<assemblyIdentity name="Microsoft.Owin" publicKeyToken="31bf3856ad364e35" culture="neutral" />
<bindingRedirect oldVersion="0.0.0.0-3.0.1.0" newVersion="3.0.1.0" />
</dependentAssembly>
<dependentAssembly>
<assemblyIdentity name="Microsoft.Owin.Security.OAuth" publicKeyToken="31bf3856ad364e35" culture="neutral" />
<bindingRedirect oldVersion="0.0.0.0-3.0.1.0" newVersion="3.0.1.0" />
</dependentAssembly>
<dependentAssembly>
<assemblyIdentity name="Microsoft.Owin.Security" publicKeyToken="31bf3856ad364e35" culture="neutral" />
<bindingRedirect oldVersion="0.0.0.0-3.0.1.0" newVersion="3.0.1.0" />
</dependentAssembly>
<dependentAssembly>
<assemblyIdentity name="Microsoft.Owin.Security.Cookies" publicKeyToken="31bf3856ad364e35" culture="neutral" />
<bindingRedirect oldVersion="0.0.0.0-3.0.1.0" newVersion="3.0.1.0" />
</dependentAssembly>