Let's start with terminology - why doesn't the package just fail. Chocolatey itself just releases over to the package to do the install. If the package is badly behaved (and it's not a badly behaved scenario that Chocolatey yet covers), then you will see behavior such as what you are seeing.
Chocolatey Execution Timeout
Chocolatey has a default timeout of 45 minutes for a package install. You can change the default timeout, see choco install -h
or https://github.com/chocolatey/choco/wiki/CommandsReference#default-options-and-switches:
--execution-timeout=VALUE
CommandExecutionTimeoutSeconds - Override the default execution
timeout in the configuration of 2700 seconds.
You can also set the value in the chocolatey.config file.
Package Issues?
If you are having issues with a package, it is best to contact the maintainers of that package on the package site https://chocolatey.org/packages/jdk8/8.0.66 :
You can also read through the disqus forum at the bottom and post there as well. That will also reach the maintainers.
Organizations Should Not Depend on the Community Feed
One last reminder - if an organization comes across this post - You should really read over why an organization should not depend on the community packages repository (aka https://chocolatey.org/packages) at organization use of Chocolatey.org. Copied here:
First of all, it goes without stating that if you are a business and
you are using Chocolatey, you should think long and hard before
trusting an external source you have no control over (chocolatey.org packages,
in addition to all of the binaries that download from official
distribution channels over the internet). It is too easy to set up your own private
feed where
you can vet packages and have complete control over the binaries and
what gets installed. This is what we recommend for businesses that use
Chocolatey in production scenarios (and what many of them do).