diff --git a/lib/vagrant/bundler.rb b/lib/vagrant/bundler.rb
index 336ac1e05..66af9763c 100644
--- a/lib/vagrant/bundler.rb
+++ b/lib/vagrant/bundler.rb
@@ -234,6 +234,8 @@ module Vagrant
         Gem::Specification.reset
       end
 
+      enable_prerelease!(specs: @initial_specifications)
+
       solution_file = load_solution_file(opts)
       @logger.debug("solution file in use for init: #{solution_file}")
 
@@ -464,6 +466,30 @@ module Vagrant
 
     protected
 
+    # This will enable prerelease if any of the root dependency constraints
+    # include prerelease versions
+    #
+    # @param [Array<Gem::Specification>] spec_list List of specifications
+    # @param [Gem::RequestSet] rs Request set of dependencies
+    def enable_prerelease!(specs: nil, request_set: nil)
+      pre = specs.detect do |spec|
+        spec.version.prerelease?
+      end if specs
+      if pre
+        @logger.debug("Enabling prerelease plugin resolution due to dependency: #{pre.full_name}")
+        ENV["VAGRANT_ALLOW_PRERELEASE"] = "1"
+        return
+      end
+      dep = request_set.dependencies.detect do |d|
+        d.prerelease?
+      end if request_set
+      if dep
+        @logger.debug("Enabling prerelease plugin resolution due to dependency: #{dep}")
+        ENV["VAGRANT_ALLOW_PRERELEASE"] = "1"
+        return
+      end
+    end
+
     def internal_install(plugins, update, **extra)
       update = {} if !update.is_a?(Hash)
       skips = []
@@ -550,6 +576,7 @@ module Vagrant
 
       # Create the request set for the new plugins
       request_set = Gem::RequestSet.new(*plugin_deps)
+      enable_prerelease!(request_set: request_set)
       request_set.prerelease = Vagrant.prerelease?
 
       installer_set = Gem::Resolver.compose_sets(
@@ -740,7 +767,6 @@ module Vagrant
               request.name == matcher["gem_name"]
             end
             if desired_activation_request && !desired_activation_request.full_spec.activated?
-              activation_request = desired_activation_request
               @logger.warn("Found misordered activation request for #{desired_activation_request.full_name}. Moving to solution HEAD.")
               solution.delete(desired_activation_request)
               solution.unshift(desired_activation_request)
@@ -813,7 +839,8 @@ module Vagrant
 
       def find_all(req)
         @specs.select do |spec|
-          allow_prerelease = spec.name == "vagrant" && Vagrant.prerelease?
+          allow_prerelease = Vagrant.allow_prerelease_dependencies? ||
+            spec.name == "vagrant" && Vagrant.prerelease?
           req.match?(spec, allow_prerelease)
         end.map do |spec|
           Gem::Resolver::InstalledSpecification.new(self, spec)
@@ -861,7 +888,7 @@ module Vagrant
       ##
       # Loads a spec with the given +name+. +version+, +platform+ and +source+ are
       # ignored.
-      def load_spec (name, version, platform, source)
+      def load_spec(name, version, platform, source)
         version = Gem::Version.new(version) if !version.is_a?(Gem::Version)
         @specs.fetch(name, []).detect{|s| s.name == name && s.version == version}
       end
diff --git a/lib/vagrant/shared_helpers.rb b/lib/vagrant/shared_helpers.rb
index ae45ea305..f14dbe08a 100644
--- a/lib/vagrant/shared_helpers.rb
+++ b/lib/vagrant/shared_helpers.rb
@@ -122,8 +122,15 @@ module Vagrant
   #
   # @return [Boolean]
   def self.prerelease?
-    !!ENV["VAGRANT_ALLOW_PRERELEASE"] ||
-      Gem::Version.new(Vagrant::VERSION).prerelease?
+    Gem::Version.new(Vagrant::VERSION).prerelease?
+  end
+
+  # This returns true/false if the Vagrant should allow prerelease
+  # versions when resolving plugin dependency constraints
+  #
+  # @return [Boolean]
+  def self.allow_prerelease_dependencies?
+    !!ENV["VAGRANT_ALLOW_PRERELEASE"]
   end
 
   # This allows control over dependency resolution when installing
diff --git a/test/unit/vagrant/bundler_test.rb b/test/unit/vagrant/bundler_test.rb
index 89391c013..8dcae5b14 100644
--- a/test/unit/vagrant/bundler_test.rb
+++ b/test/unit/vagrant/bundler_test.rb
@@ -618,6 +618,117 @@ describe Vagrant::Bundler do
         end
       end
     end
+
+    describe "#enable_prerelease!" do
+      before do
+        @_ev = ENV.delete("VAGRANT_ALLOW_PRERELEASE")
+      end
+
+      after do
+        ENV["VAGRANT_ALLOW_PRERELEASE"] = @_ev
+      end
+
+      context "with specification list" do
+        let(:specifications) { [] }
+
+        it "should not modify prerelease by default" do
+          subject.send(:enable_prerelease!, specs: specifications)
+          expect(ENV["VAGRANT_ALLOW_PRERELEASE"]).to be_falsey
+        end
+
+        it "should not have enabled allow prerelease dependencies" do
+          subject.send(:enable_prerelease!, specs: specifications)
+          expect(Vagrant.allow_prerelease_dependencies?).to be_falsey
+        end
+
+        context "when specifications do not contain prerelease versions" do
+          let(:specifications) { [
+            double("spec1", full_name: "spec1", version: double("version1", prerelease?: false)),
+            double("spec2", full_name: "spec2", version: double("version2", prerelease?: false)),
+            double("spec3", full_name: "spec3", version: double("version3", prerelease?: false))
+          ] }
+
+          it "should not modify prerelease" do
+            subject.send(:enable_prerelease!, specs: specifications)
+            expect(ENV["VAGRANT_ALLOW_PRERELEASE"]).to be_falsey
+          end
+
+          it "should not have enabled allow prerelease dependencies" do
+            subject.send(:enable_prerelease!, specs: specifications)
+            expect(Vagrant.allow_prerelease_dependencies?).to be_falsey
+          end
+        end
+
+        context "when specifications contain prerelease versions" do
+          let(:specifications) { [
+            double("spec1", full_name: "spec1", version: double("version1", prerelease?: false)),
+            double("spec2", full_name: "spec2", version: double("version2", prerelease?: true)),
+            double("spec3", full_name: "spec3", version: double("version3", prerelease?: false))
+          ] }
+
+          it "should enable prerelease" do
+            subject.send(:enable_prerelease!, specs: specifications)
+            expect(ENV["VAGRANT_ALLOW_PRERELEASE"]).to be_truthy
+          end
+
+          it "should have enabled allow prerelease dependencies" do
+            subject.send(:enable_prerelease!, specs: specifications)
+            expect(Vagrant.allow_prerelease_dependencies?).to be_truthy
+          end
+        end
+      end
+
+      context "with request set" do
+        let(:request_set) { double("request_set", dependencies: dependencies) }
+        let(:dependencies) { [] }
+
+        it "should not modify prerelease by default" do
+          subject.send(:enable_prerelease!, request_set: request_set)
+          expect(ENV["VAGRANT_ALLOW_PRERELEASE"]).to be_falsey
+        end
+
+        it "should not have enabled allow prerelease dependencies" do
+          subject.send(:enable_prerelease!, request_set: request_set)
+          expect(Vagrant.allow_prerelease_dependencies?).to be_falsey
+        end
+
+        context "when specifications do not contain prerelease versions" do
+          let(:dependencies) { [
+            double("dep1", prerelease?: false, to_s: nil),
+            double("dep2", prerelease?: false, to_s: nil),
+            double("dep3", prerelease?: false, to_s: nil)
+          ] }
+
+          it "should not modify prerelease" do
+            subject.send(:enable_prerelease!, request_set: request_set)
+            expect(ENV["VAGRANT_ALLOW_PRERELEASE"]).to be_falsey
+          end
+
+          it "should not have enabled allow prerelease dependencies" do
+            subject.send(:enable_prerelease!, request_set: request_set)
+            expect(Vagrant.allow_prerelease_dependencies?).to be_falsey
+          end
+        end
+
+        context "when specifications contain prerelease versions" do
+          let(:dependencies) { [
+            double("dep1", prerelease?: false, to_s: nil),
+            double("dep2", prerelease?: true, to_s: nil),
+            double("dep3", prerelease?: false, to_s: nil)
+          ] }
+
+          it "should enable prerelease" do
+            subject.send(:enable_prerelease!, request_set: request_set)
+            expect(ENV["VAGRANT_ALLOW_PRERELEASE"]).to be_truthy
+          end
+
+          it "should have enabled allow prerelease dependencies" do
+            subject.send(:enable_prerelease!, request_set: request_set)
+            expect(Vagrant.allow_prerelease_dependencies?).to be_truthy
+          end
+        end
+      end
+    end
   end
 
   describe Vagrant::Bundler::PluginSet do
diff --git a/test/unit/vagrant/shared_helpers_test.rb b/test/unit/vagrant/shared_helpers_test.rb
index 781c882ea..a2d1b5b59 100644
--- a/test/unit/vagrant/shared_helpers_test.rb
+++ b/test/unit/vagrant/shared_helpers_test.rb
@@ -142,24 +142,22 @@ describe Vagrant do
       stub_const("Vagrant::VERSION", "1.0.0")
       expect(subject.prerelease?).to be(false)
     end
+  end
 
+  describe ".allow_prerelease_dependencies?" do
     context "with environment variable set" do
       before { allow(ENV).to receive(:[]).with("VAGRANT_ALLOW_PRERELEASE").and_return("1") }
 
-      context "when version is development version" do
-        before { stub_const("Vagrant::VERSION", "1.0.0.dev") }
-
-        it "should return true" do
-          expect(subject.prerelease?).to be(true)
-        end
+      it "should return true" do
+        expect(subject.allow_prerelease_dependencies?).to be(true)
       end
+    end
 
-      context "when version is non-development version" do
-        before { stub_const("Vagrant::VERSION", "1.0.0") }
+    context "with environment variable unset" do
+      before { allow(ENV).to receive(:[]).with("VAGRANT_ALLOW_PRERELEASE").and_return(nil) }
 
-        it "should return true" do
-          expect(subject.prerelease?).to be(true)
-        end
+      it "should return false" do
+        expect(subject.allow_prerelease_dependencies?).to be(false)
       end
     end
   end