diff --git a/lib/vagrant/action/builtin/box_remove.rb b/lib/vagrant/action/builtin/box_remove.rb
index 1d0cea7fd..5d18ed704 100644
--- a/lib/vagrant/action/builtin/box_remove.rb
+++ b/lib/vagrant/action/builtin/box_remove.rb
@@ -15,6 +15,7 @@ module Vagrant
           box_provider = env[:box_provider]
           box_provider = box_provider.to_sym if box_provider
           box_version  = env[:box_version]
+          box_remove_all_versions = env[:box_remove_all_versions]
 
           boxes = {}
           env[:box_collection].all.each do |n, v, p|
@@ -53,7 +54,7 @@ module Vagrant
             if all_versions.length == 1
               # There is only one version, just use that.
               box_version = all_versions.first
-            else
+            elsif not box_remove_all_versions
               # There are multiple versions, we can't choose.
               raise Errors::BoxRemoveMultiVersion,
                 name: box_name,
@@ -68,48 +69,53 @@ module Vagrant
               versions: all_versions.sort.map { |k| " * #{k}" }.join("\n")
           end
 
-          box = env[:box_collection].find(
-            box_name, box_provider, box_version)
+          versions_to_remove = [box_version]
+          versions_to_remove = all_versions if box_remove_all_versions
 
-          # Verify that this box is not in use by an active machine,
-          # otherwise warn the user.
-          users = box.in_use?(env[:machine_index]) || []
-          users = users.find_all { |u| u.valid?(env[:home_path]) }
-          if !users.empty?
-            # Build up the output to show the user.
-            users = users.map do |entry|
-              "#{entry.name} (ID: #{entry.id})"
-            end.join("\n")
+          versions_to_remove.sort.each do |version_to_remove|
+            box = env[:box_collection].find(
+              box_name, box_provider, box_version)
 
-            force_key = :force_confirm_box_remove
-            message   = I18n.t(
-              "vagrant.commands.box.remove_in_use_query",
-              name: box.name,
-              provider: box.provider,
-              version: box.version,
-              users: users) + " "
+            # Verify that this box is not in use by an active machine,
+            # otherwise warn the user.
+            users = box.in_use?(env[:machine_index]) || []
+            users = users.find_all { |u| u.valid?(env[:home_path]) }
+            if !users.empty?
+              # Build up the output to show the user.
+              users = users.map do |entry|
+                "#{entry.name} (ID: #{entry.id})"
+              end.join("\n")
 
-            # Ask the user if we should do this
-            stack = Builder.new.tap do |b|
-              b.use Confirm, message, force_key
+              force_key = :force_confirm_box_remove
+              message   = I18n.t(
+                "vagrant.commands.box.remove_in_use_query",
+                name: box.name,
+                provider: box.provider,
+                version: box.version,
+                users: users) + " "
+
+              # Ask the user if we should do this
+              stack = Builder.new.tap do |b|
+                b.use Confirm, message, force_key
+              end
+
+              result = env[:action_runner].run(stack, env)
+              if !result[:result]
+                # They said "no", so continue with the next box
+                next
+              end
             end
 
-            result = env[:action_runner].run(stack, env)
-            if !result[:result]
-              # They said "no", so just return
-              return @app.call(env)
-            end
+            env[:ui].info(I18n.t("vagrant.commands.box.removing",
+                                name: box.name,
+                                provider: box.provider,
+                                version: box.version))
+            box.destroy!
+
+            # Passes on the removed box to the rest of the middleware chain
+            env[:box_removed] = box
           end
 
-          env[:ui].info(I18n.t("vagrant.commands.box.removing",
-                              name: box.name,
-                              provider: box.provider,
-                              version: box.version))
-          box.destroy!
-
-          # Passes on the removed box to the rest of the middleware chain
-          env[:box_removed] = box
-
           @app.call(env)
         end
       end
diff --git a/plugins/commands/box/command/remove.rb b/plugins/commands/box/command/remove.rb
index 013ca2921..4bedd96c0 100644
--- a/plugins/commands/box/command/remove.rb
+++ b/plugins/commands/box/command/remove.rb
@@ -27,6 +27,10 @@ module VagrantPlugins
                  "The specific version of the box to remove") do |v|
               options[:version] = v
             end
+
+            o.on("--all", "Remove all available versions of the box") do |a|
+              options[:all] = a
+            end
           end
 
           # Parse the options
@@ -50,6 +54,7 @@ module VagrantPlugins
             box_provider: options[:provider],
             box_version:  options[:version],
             force_confirm_box_remove: options[:force],
+            box_remove_all_versions: options[:all],
           })
 
           # Success, exit status 0
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index 3b7094310..16c8b4e5d 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -556,8 +556,8 @@ en:
         You requested to remove the box '%{name}' with provider
         '%{provider}'. This box has multiple versions. You must
         explicitly specify which version you want to remove with
-        the `--box-version` flag. The available versions for this
-        box are:
+        the `--box-version` flag or specify the `--all` flag to remove all
+        versions. The available versions for this box are:
 
         %{versions}
       box_remove_not_found: |-
diff --git a/website/docs/source/v2/cli/box.html.md b/website/docs/source/v2/cli/box.html.md
index e919fc9ad..24cacbe30 100644
--- a/website/docs/source/v2/cli/box.html.md
+++ b/website/docs/source/v2/cli/box.html.md
@@ -128,13 +128,16 @@ This command removes a box from Vagrant that matches the given name.
 
 If a box has multiple providers, the exact provider must be specified
 with the `--provider` flag. If a box has multiple versions, you can select
-what versions to delete with the `--box-version` flag.
+what versions to delete with the `--box-version` flag or remove all versions
+with the `--all` flag.
 
 ## Options
 
 * `--box-version VALUE` - Version of version constraints of the boxes to
   remove. See documentation on this flag for `box add` for more details.
 
+* `--all` - Remove all available versions of a box.
+
 * `--force` - Forces removing the box even if an active Vagrant
   environment is using it.