ProGet returns an HTTP 404 while pushing a large package

Trying to push a 30MB NuGet package I get this error:

System.InvalidOperationException: Failed to process request. 'Not Found'.
The remote server returned an error: (404) Not Found.. ---> System.Net.WebException: The remote server returned an error: (404) Not Found.
at System.Net.HttpWebRequest.GetResponse()
at NuGet.RequestHelper.GetResponse(Func1 createRequest, Action1 prepareRequest, IProxyCache proxyCache, ICredentialCache credentialCache, ICredentialProvider credentialProvider)
at NuGet.HttpClient.GetResponse()
at NuGet.PackageServer.EnsureSuccessfulResponse(HttpClient client, Nullable1 expectedStatusCode) --- End of inner exception stack trace --- at NuGet.PackageServer.EnsureSuccessfulResponse(HttpClient client, Nullable1 expectedStatusCode)
at NuGet.PackageServer.PushPackageToServer(String apiKey, Func`1 packageStreamFactory, Int32 timeout)
at NuGet.PackageServer.PushPackage(String apiKey, IPackage package, Int32 timeout)
at NuGet.Commands.PushCommand.PushPackageCore(String source, String apiKey, PackageServer packageServer, String packageToPush, TimeSpan timeout)
at NuGet.Commands.PushCommand.PushPackage(String packagePath, String source,String apiKey, TimeSpan timeout)
at NuGet.Commands.PushCommand.ExecuteCommand()
at NuGet.Commands.Command.Execute()
at NuGet.Program.Main(String[] args)

ProGet 2.1.0 installed on a Windows Server 2008 R2 machine, under IIS.

Package structure:

lib\net40\foo.dll
tools\file1
tools\file2
tools\file3
tools\file4
tools\file5
tools\file6

The push succeeds if I remove one file from the package (size drops to 28 MB).

Is there a package size limit?
Can I enable some server side logs in order to have meaningful errors?

~30mb should be fine; there are no package-size limits imposed, but perhaps IIS is timing out the request, or filtering based on size?

Can you check the IIS settings for this? Perhaps increase maxRequestLength and executionTimeout?

Thank you Alex,

as you suggested, the issue has been solved increasing the maximum allowed content length in IIS.