diff --git a/lib/cli/ui/prompt.rb b/lib/cli/ui/prompt.rb
index 3f106a38d..7fcc3bcb3 100644
--- a/lib/cli/ui/prompt.rb
+++ b/lib/cli/ui/prompt.rb
@@ -71,13 +71,13 @@ class << self
         #     handler.option('python') { |selection| selection }
         #   end
         #
-        def ask(question, options: nil, default: nil, is_file: nil, allow_empty: true, &options_proc)
+        def ask(question, options: nil, default: nil, is_file: nil, allow_empty: true, multiple: false, &options_proc)
           if ((options || block_given?) && (default || is_file))
             raise(ArgumentError, 'conflicting arguments: options provided with default or is_file')
           end
 
           if options || block_given?
-            ask_interactive(question, options, &options_proc)
+            ask_interactive(question, options, multiple: multiple, &options_proc)
           else
             ask_free_form(question, default, is_file, allow_empty)
           end
@@ -121,7 +121,7 @@ def ask_free_form(question, default, is_file, allow_empty)
           end
         end
 
-        def ask_interactive(question, options = nil)
+        def ask_interactive(question, options = nil, multiple: false)
           raise(ArgumentError, 'conflicting arguments: options and block given') if options && block_given?
 
           options ||= if block_given?
@@ -131,23 +131,36 @@ def ask_interactive(question, options = nil)
           end
 
           raise(ArgumentError, 'insufficient options') if options.nil? || options.size < 2
-          puts_question("#{question} {{yellow:(choose with ↑ ↓ ⏎)}}")
-          resp = interactive_prompt(options)
+          instructions = (multiple ? "Toogle options. " : "") + "Choose with ↑ ↓ ⏎"
+          puts_question("#{question} {{yellow:(#{instructions})}}")
+          resp = interactive_prompt(options, multiple: multiple)
 
           # Clear the line, and reset the question to include the answer
           print(ANSI.previous_line + ANSI.end_of_line + ' ')
           print(ANSI.cursor_save)
           print(' ' * CLI::UI::Terminal.width)
           print(ANSI.cursor_restore)
-          puts_question("#{question} (You chose: {{italic:#{resp}}})")
+
+          resp_text = resp
+          if multiple
+            resp_text = case resp.size
+            when 0
+              "<nothing>"
+            when 1..2
+              resp.join(" and ")
+            else
+              "#{resp.size} items"
+            end
+          end
+          puts_question("#{question} (You chose: {{italic:#{resp_text}}})")
 
           return handler.call(resp) if block_given?
           resp
         end
 
         # Useful for stubbing in tests
-        def interactive_prompt(options)
-          InteractiveOptions.call(options)
+        def interactive_prompt(options, multiple: false)
+          InteractiveOptions.call(options, multiple: multiple)
         end
 
         def write_default_over_empty_input(default)
diff --git a/lib/cli/ui/prompt/interactive_options.rb b/lib/cli/ui/prompt/interactive_options.rb
index 96269782d..fdcd08367 100644
--- a/lib/cli/ui/prompt/interactive_options.rb
+++ b/lib/cli/ui/prompt/interactive_options.rb
@@ -4,6 +4,9 @@ module CLI
   module UI
     module Prompt
       class InteractiveOptions
+        DONE = "Done"
+        CHECKBOX_ICON = { false => "⬡", true => "⬢" }
+
         # Prompts the user with options
         # Uses an interactive session to allow the user to pick an answer
         # Can use arrows, y/n, numbers (1/2), and vim bindings to control
@@ -15,9 +18,14 @@ class InteractiveOptions
         # Ask an interactive question
         #   CLI::UI::Prompt::InteractiveOptions.call(%w(rails go python))
         #
-        def self.call(options)
-          list = new(options)
-          options[list.call - 1]
+        def self.call(options, multiple: false)
+          list = new(options, multiple: multiple)
+          selected = list.call
+          if multiple
+            selected.map { |s| options[s - 1] }
+          else
+            options[selected - 1]
+          end
         end
 
         # Initializes a new +InteractiveOptions+
@@ -27,12 +35,15 @@ def self.call(options)
         #
         #   CLI::UI::Prompt::InteractiveOptions.new(%w(rails go python))
         #
-        def initialize(options)
+        def initialize(options, multiple: false)
           @options = options
           @active = 1
           @marker = '>'
           @answer = nil
           @state = :root
+          @multiple = multiple
+          @chosen = Array.new(@options.size) { false } if multiple
+          @redraw = true
         end
 
         # Calls the +InteractiveOptions+ and asks the question
@@ -42,7 +53,7 @@ def call
           CLI::UI.raw { print(ANSI.hide_cursor) }
           while @answer.nil?
             render_options
-            wait_for_actionable_user_input
+            wait_for_redraw
             reset_position
           end
           clear_output
@@ -89,16 +100,32 @@ def num_lines
         ESC = "\e"
 
         def up
-          @active = @active - 1 >= 1 ? @active - 1 : @options.length
+          min_pos = @multiple ? 0 : 1
+          @active = @active - 1 >= min_pos ? @active - 1 : @options.length
+          @redraw = true
         end
 
         def down
-          @active = @active + 1 <= @options.length ? @active + 1 : 1
+          min_pos = @multiple ? 0 : 1
+          @active = @active + 1 <= @options.length ? @active + 1 : min_pos
+          @redraw = true
         end
 
         def select_n(n)
           @active = n
-          @answer = n
+          if @multiple
+            if n == 0
+              @answer = []
+              @chosen.each_with_index do |selected, i|
+                @answer << i + 1 if selected
+              end
+            else
+              @chosen[n - 1] = !@chosen[n - 1]
+            end
+          else
+            @answer = n
+          end
+          @redraw = true
         end
 
         def select_bool(char)
@@ -106,13 +133,16 @@ def select_bool(char)
           opt = @options.detect { |o| o.start_with?(char) }
           @active = @options.index(opt) + 1
           @answer = @options.index(opt) + 1
+          @redraw = true
         end
 
-        def wait_for_actionable_user_input
-          last_active = @active
-          while @active == last_active && @answer.nil?
-            wait_for_user_input
-          end
+        def select_current
+          select_n(@active)
+        end
+
+        def wait_for_redraw
+          @redraw = false
+          wait_for_user_input until @redraw
         end
 
         # rubocop:disable Style/WhenThen,Layout/SpaceBeforeSemicolon
@@ -125,10 +155,11 @@ def wait_for_user_input
             when ESC                       ; @state = :esc
             when 'k'                       ; up
             when 'j'                       ; down
+            when '0'                       ; select_n(char.to_i)
             when ('1'..@options.size.to_s) ; select_n(char.to_i)
             when 'y', 'n'                  ; select_bool(char)
-            when " ", "\r", "\n"           ; @answer = @active # <enter>
-            when "\u0003"                  ; raise Interrupt   # Ctrl-c
+            when " ", "\r", "\n"           ; select_current  # <enter>
+            when "\u0003"                  ; raise Interrupt # Ctrl-c
             end
           when :esc
             case char
@@ -169,6 +200,8 @@ def presented_options(recalculate: false)
           return @presented_options unless recalculate
 
           @presented_options = @options.zip(1..Float::INFINITY)
+          @presented_options.unshift([DONE, 0]) if @multiple
+
           while num_lines > max_options
             # try to keep the selection centered in the window:
             if distance_from_selection_to_end > distance_from_start_to_selection
@@ -203,7 +236,6 @@ def ensure_first_item_is_continuation_marker
           @presented_options.unshift(["...", nil]) if @presented_options.first.last
         end
 
-
         def max_options
           @max_options ||= CLI::UI::Terminal.height - 2 # Keeps a one line question visible
         end
@@ -214,6 +246,7 @@ def render_options
           presented_options(recalculate: true).each do |choice, num|
             padding = ' ' * (max_num_length - num.to_s.length)
             message = "  #{num}#{num ? '.' : ' '}#{padding}"
+            message += " #{CHECKBOX_ICON[@chosen[num - 1]]} " if @multiple && num && num > 0
             message += choice.split("\n").map { |l| " {{bold:#{l}}}" }.join("\n")
 
             if num == @active