diff --git a/CHANGELOG.md b/CHANGELOG.md
index bc2bfa56f..201a7ffc7 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -25,6 +25,7 @@ BUG FIXES:
   - core: Fix a rare issue where vagrant up would complain it couldn't
       check version of a box that doesn't exist. [GH-3326]
   - commands/box: Show versions when listing. [GH-3316]
+  - commands/box: Outdated check can list local boxes that are newer. [GH-3321]
   - commands/status: Machine readable output contains the target. [GH-3218]
   - guests/arch: Reload udev rules after network change. [GH-3322]
   - guests/debian: Changing host name works properly. [GH-3283]
diff --git a/lib/vagrant/action/builtin/box_check_outdated.rb b/lib/vagrant/action/builtin/box_check_outdated.rb
index fcd88c384..a134f294b 100644
--- a/lib/vagrant/action/builtin/box_check_outdated.rb
+++ b/lib/vagrant/action/builtin/box_check_outdated.rb
@@ -54,6 +54,8 @@ module Vagrant
               name: update[0].name,
               current: box.version,
               latest: update[1].version))
+          else
+            check_outdated_local(env)
           end
 
           @app.call(env)
@@ -61,9 +63,15 @@ module Vagrant
 
         def check_outdated_local(env)
           machine = env[:machine]
+
+          # Make sure we respect the constraints set within the Vagrantfile
+          version = machine.config.vm.box_version
+          version += ", " if version
+          version ||= ""
+          version += "> #{machine.box.version}"
+
           box = env[:box_collection].find(
-            machine.box.name, machine.box.provider,
-            "> #{machine.box.version}")
+            machine.box.name, machine.box.provider, version)
           if box
             env[:ui].warn(I18n.t(
               "vagrant.box_outdated_local",
diff --git a/test/unit/vagrant/action/builtin/box_check_outdated_test.rb b/test/unit/vagrant/action/builtin/box_check_outdated_test.rb
index 9e1a2051e..0112d2656 100644
--- a/test/unit/vagrant/action/builtin/box_check_outdated_test.rb
+++ b/test/unit/vagrant/action/builtin/box_check_outdated_test.rb
@@ -127,6 +127,32 @@ describe Vagrant::Action::Builtin::BoxCheckOutdated do
       expect(env[:box_outdated]).to be_true
     end
 
+    it "has an update if it is local" do
+      iso_env.box3("foo", "1.1", :virtualbox)
+
+      expect(box).to receive(:has_update?).and_return(nil)
+
+      expect(app).to receive(:call).with(env).once
+
+      subject.call(env)
+
+      expect(env[:box_outdated]).to be_true
+    end
+
+    it "does not have a local update if not within constraints" do
+      iso_env.box3("foo", "1.1", :virtualbox)
+
+      machine.config.vm.box_version = "> 1.0, < 1.1"
+
+      expect(box).to receive(:has_update?).and_return(nil)
+
+      expect(app).to receive(:call).with(env).once
+
+      subject.call(env)
+
+      expect(env[:box_outdated]).to be_false
+    end
+
     it "raises error if has_update? errors" do
       expect(box).to receive(:has_update?).and_raise(Vagrant::Errors::VagrantError)