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Vagrant 1.8.7 fails to fetch Jessie image with vague error message
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I had vagrant 1.8.7 sitting around on my Mac (current is 1.9.1) and got this vague error when it tried to fetch the Jessie base image:

Orac:mwv-jessie brion$ vagrant up
Bringing machine 'default' up with 'virtualbox' provider...
==> default: Box 'debian/contrib-jessie64' could not be found. Attempting to find and install...
    default: Box Provider: virtualbox
    default: Box Version: >= 0
The box 'debian/contrib-jessie64' could not be found or
could not be accessed in the remote catalog. If this is a private
box on HashiCorp's Atlas, please verify you're logged in via
`vagrant login`. Also, please double-check the name. The expanded
URL and error message are shown below:

URL: [""]

After updating to Vagrant 1.9.1, expunging plugins, and re-running, it appears to be loading up correctly.

Perhaps Vagrant 1.8.x is no longer compatible? If so should probably check for it and warn.

Event Timeline

I don't see anything at that explicitly says a required minimum Vagrant version. We do have Vagrant.require_version '>= 1.7.0' in our Vagrantfile because the plugin loading method we are using these days only works in 1.7.0+.

The error you gave looks vaguely like an intermittent network or server error from, but I have no way to verify that.

Running with --debug seems to indicate that Vagrant's downloader is failing to load curl or some such junk:

 INFO downloader: HEAD:
 INFO subprocess: Starting process: ["/opt/vagrant/embedded/bin/curl", "-I", "-q", "--fail", "--location", "--max-redirs", "10", "--user-agent", "Vagrant/1.8.7 (+; ruby2.2.5)", "--continue-at", "-", "-H", "Accept: application/json", ""]
 INFO subprocess: Command in the installer. Specifying DYLD_LIBRARY_PATH...
DEBUG subprocess: Selecting on IO
DEBUG subprocess: stderr: dyld: Library not loaded: @rpath/libcurl.4.dylib
  Referenced from: /opt/vagrant/embedded/bin/curl
  Reason: Incompatible library version: curl requires version 9.0.0 or later, but libcurl.4.dylib provides version 7.0.0
DEBUG subprocess: Waiting for process to exit. Remaining to timeout: 32000
DEBUG subprocess: Exit status: 6
 WARN downloader: Downloader exit code: 6

So this may be a vagrant 1.8 vs macOS 10.12 upgrade problem, and not general to working instances of 1.8.

Looks like upstream

So vagrant 1.8 other variants and other OSs should be fine. Closing out.