diff --git a/Casks/vagrant.rb b/Casks/vagrant.rb
index 79ae0b6f29c..0488b9897e5 100644
--- a/Casks/vagrant.rb
+++ b/Casks/vagrant.rb
@@ -5,12 +5,21 @@ cask 'vagrant' do
   # hashicorp.com/vagrant was verified as official when first introduced to the cask
   url "https://releases.hashicorp.com/vagrant/#{version}/vagrant_#{version}.dmg"
   appcast 'https://github.com/mitchellh/vagrant/releases.atom',
-          checkpoint: '5b1451672c9d60925f947f676d56250f5d5572462abcba4f8ef8fc043a4cb7fc'
+          checkpoint: '8d16ac5df154d7b39604d9f6505b17394cdc45205c6a75a1bac8d9ff39cc2f06'
   name 'Vagrant'
   homepage 'https://www.vagrantup.com/'
 
   pkg 'Vagrant.pkg'
 
+  # Vagrant 1.8.7 ships with a broken embedded curl. Removing it causes vagrant
+  # to fall back to the system-installed curl, which works.
+  # https://github.com/mitchellh/vagrant/issues/7969
+  postflight do
+    system_command '/bin/rm',
+                   args: ['/opt/vagrant/embedded/bin/curl'],
+                   sudo: true
+  end
+
   uninstall script:  { executable: 'uninstall.tool', input: %w[Yes] },
             pkgutil: 'com.vagrant.vagrant'