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A workaround for now is to simply place the larger package in the "App_Data\packages" folder or to create a share to that (and lock it down to only folks who should have access to push packages). The server will process that package and move it into a subfolder - that's when it is ready for consumption by Chocolatey.
Also note that you can only place a version of a package one time due to immutability. If you need to put a fix in, you need to rev the package version up to do so.
There is a known issue somewhere in the used NuGet code base that will timeout when attempting to push very large files.
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