diff --git a/CHANGELOG.md b/CHANGELOG.md
index 692c64787..11d732745 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -24,6 +24,7 @@ BUG FIXES:
   - core: Better error message when adding a box with a malformed version. [GH-3332]
   - core: Fix a rare issue where vagrant up would complain it couldn't
       check version of a box that doesn't exist. [GH-3326]
+  - core: Box version constraint can't be specified with old-style box. [GH-3260]
   - 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   - commands/box: Outdated check can list local boxes that are newer.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]
diff --git a/lib/vagrant/action/builtin/box_add.rb b/lib/vagrant/action/builtin/box_add.rb
index 5b199f78a..81cf19744 100644
--- a/lib/vagrant/action/builtin/box_add.rb
+++ b/lib/vagrant/action/builtin/box_add.rb
@@ -119,6 +119,10 @@ module Vagrant
             raise Errors::BoxAddNameRequired
           end
 
+          if env[:box_version]
+            raise Errors::BoxAddDirectVersion
+          end
+
           provider = env[:box_provider]
           provider = Array(provider) if provider
 
diff --git a/lib/vagrant/errors.rb b/lib/vagrant/errors.rb
index a886560ca..d89b61fa2 100644
--- a/lib/vagrant/errors.rb
+++ b/lib/vagrant/errors.rb
@@ -120,6 +120,10 @@ module Vagrant
       error_key(:batch_multi_error)
     end
 
+    class BoxAddDirectVersion < VagrantError
+      error_key(:box_add_direct_version)
+    end
+
     class BoxAddMetadataMultiURL < VagrantError
       error_key(:box_add_metadata_multi_url)
     end
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index b4017f3b3..e73ce8b0c 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -336,6 +336,11 @@ en:
         Name: %{name}
         Provider: %{provider}
         Version: %{version}
+      box_add_direct_version: |-
+        You specified a box version constraint with a direct box file
+        path. Box version constraints only work with boxes from Vagrant
+        Cloud or a custom box host. Please remove the version constraint
+        and try again.
       box_add_metadata_multi_url: |-
         Multiple URLs for a box can't be specified when adding
         versioned boxes. Please specify a single URL to the box
diff --git a/test/unit/vagrant/action/builtin/box_add_test.rb b/test/unit/vagrant/action/builtin/box_add_test.rb
index e59682fae..44cf1b9b6 100644
--- a/test/unit/vagrant/action/builtin/box_add_test.rb
+++ b/test/unit/vagrant/action/builtin/box_add_test.rb
@@ -177,6 +177,21 @@ describe Vagrant::Action::Builtin::BoxAdd do
         to raise_error(Vagrant::Errors::DownloaderError)
     end
 
+    it "raises an error if a version was specified" do
+      box_path = iso_env.box2_file(:virtualbox)
+
+      env[:box_name] = "foo"
+      env[:box_url] = box_path.to_s
+      env[:box_version] = "1"
+
+      expect(box_collection).to receive(:add).never
+
+      expect(app).to receive(:call).never
+
+      expect { subject.call(env) }.
+        to raise_error(Vagrant::Errors::BoxAddDirectVersion)
+    end
+
     it "force adds if exists and specified" do
       box_path = iso_env.box2_file(:virtualbox)