diff --git a/lib/vagrant/box_collection.rb b/lib/vagrant/box_collection.rb
index 6e83ad4ee..24e1c7124 100644
--- a/lib/vagrant/box_collection.rb
+++ b/lib/vagrant/box_collection.rb
@@ -276,17 +276,16 @@ module Vagrant
           next if versiondir.basename.to_s.start_with?(".")
 
           version = versiondir.basename.to_s
-          Gem::Version.new(version)
         end.compact
 
         # Traverse through versions with the latest version first
         versions.sort.reverse.each do |v|
-          if !requirements.all? { |r| r.satisfied_by?(v) }
+          if !requirements.all? { |r| r.satisfied_by?(Gem::Version.new(v)) }
             # Unsatisfied version requirements
             next
           end
 
-          versiondir = box_directory.join(v.to_s)
+          versiondir = box_directory.join(v)
           providers.each do |provider|
             provider_dir = versiondir.join(provider.to_s)
             next if !provider_dir.directory?
@@ -303,7 +302,7 @@ module Vagrant
             end
 
             return Box.new(
-              name, provider, v.to_s, provider_dir,
+              name, provider, v, provider_dir,
               metadata_url: metadata_url,
             )
           end
diff --git a/test/unit/vagrant/box_collection_test.rb b/test/unit/vagrant/box_collection_test.rb
index f0e5e0edc..21a39ae70 100644
--- a/test/unit/vagrant/box_collection_test.rb
+++ b/test/unit/vagrant/box_collection_test.rb
@@ -194,6 +194,19 @@ describe Vagrant::BoxCollection, :skip_windows do
       expect(result.version).to eq("1.0")
     end
 
+    it "handles prerelease versions" do
+      # Create the "box"
+      environment.box3("foo", "0.1.0-alpha.1", :virtualbox)
+      environment.box3("foo", "0.1.0-alpha.2", :virtualbox)
+
+      # Actual test
+      result = subject.find("foo", :virtualbox, ">= 0")
+      expect(result).to_not be_nil
+      expect(result).to be_kind_of(box_class)
+      expect(result.name).to eq("foo")
+      expect(result.version).to eq("0.1.0-alpha.2")
+    end
+
     it "returns nil if a box's constraints can't be satisfied" do
       # Create the "box"
       environment.box3("foo", "0.1", :virtualbox)