@joshuagilman_1054 that's really large chocolatey file (nuget package), so you may want to rethink your approach. It'll cause some pain across the board, as you try to download and install that file as well. Instead, perhaps have your chocolatey package download an asset that you've stored in ProGet instead?
In general, large files are tricky to publish over a single HTTP request reliably. This is across the board, even when uploading files to places like Amazon S3; those rely on a chunked uploading process... but the NuGet API doesn't support that.
Otherwise, there's no limit imposed by ProGet itself, and you've found the settings that ASP.NET imposes. There could be some other limitation happening, but it's hard to say where; apparently it varies by operating system version, and it might even be middleware (like a proxy/firewall).
The message "there must be exactly one package" is unexpected; I would instead expect 'request length exceed". In any case, that message just means that no valid files were attached to the request, which can happen if it was suddenly cut off.
All told, when it comes to really large files (even asset directories), a Drop Path approach may be easiest to use.
