diff --git a/bundler/lib/bundler/cli.rb b/bundler/lib/bundler/cli.rb
index 0f234f26b956..6bb1f561c28d 100644
--- a/bundler/lib/bundler/cli.rb
+++ b/bundler/lib/bundler/cli.rb
@@ -185,6 +185,12 @@ def help(cli = nil)
     end
 
     def self.handle_no_command_error(command, has_namespace = $thor_runner)
+      if command == "upgrade"
+        command = Bundler.ui.add_color("bundle update <gem_name>", :bold, :cyan)
+        Bundler.ui.info("Please use #{command} to update gems in your bundle.")
+        exit(1)
+      end
+
       if Bundler.settings[:plugins] && Bundler::Plugin.command?(command)
         return Bundler::Plugin.exec_command(command, ARGV[1..-1])
       end
diff --git a/bundler/spec/other/cli_dispatch_spec.rb b/bundler/spec/other/cli_dispatch_spec.rb
index a2c745b0703d..bc0a3016dd19 100644
--- a/bundler/spec/other/cli_dispatch_spec.rb
+++ b/bundler/spec/other/cli_dispatch_spec.rb
@@ -17,4 +17,10 @@
     bundle "in", raise_on_error: false
     expect(err).to eq("Ambiguous command in matches [info, init, install]")
   end
+
+  it "prints a helpful message for 'upgrade'" do
+    bundle "upgrade", raise_on_error: false
+    expect(out).to eq("Please use bundle update <gem_name> to update gems in your bundle.")
+    expect(exitstatus).to eq(1)
+  end
 end
diff --git a/lib/rubygems/exceptions.rb b/lib/rubygems/exceptions.rb
index 40485bbadff8..2f100cd35f13 100644
--- a/lib/rubygems/exceptions.rb
+++ b/lib/rubygems/exceptions.rb
@@ -26,6 +26,44 @@ def self.attach_correctable
       DidYouMean.correct_error(Gem::UnknownCommandError, Gem::UnknownCommandSpellChecker)
     end
   end
+
+  def detailed_message(highlight: true, **)
+    msg = super(highlight: highlight)
+
+    case unknown_command
+    when "upgrade"
+      command = "bundle update <gem_name>"
+
+      bold = "\e[1m"
+      cyan = "\e[36m"
+      reset = "\e[0m"
+
+      command = if highlight && can_display_colors?
+        "#{bold}#{cyan}#{command}#{reset}"
+      else
+        "`#{command}`"
+      end
+
+      msg + "\nPlease use #{command} to update gems in your bundle."
+
+    else
+      msg
+    end
+  end
+
+  private
+
+  def can_display_colors?
+    are_colors_supported? && !are_colors_disabled?
+  end
+
+  def are_colors_supported?
+    stdout.tty? && ENV["TERM"] != "dumb"
+  end
+
+  def are_colors_disabled?
+    !ENV["NO_COLOR"].nil? && !ENV["NO_COLOR"].empty?
+  end
 end
 
 class Gem::DependencyError < Gem::Exception; end
diff --git a/test/rubygems/test_gem_command_manager.rb b/test/rubygems/test_gem_command_manager.rb
index 889d5ce9e66a..55d4d573e37c 100644
--- a/test/rubygems/test_gem_command_manager.rb
+++ b/test/rubygems/test_gem_command_manager.rb
@@ -91,6 +91,24 @@ def test_find_command_unknown_suggestions
     assert_equal message, actual_message
   end
 
+  def test_upgrade_points_users_to_update
+    e = assert_raise Gem::UnknownCommandError do
+      @command_manager.find_command "upgrade"
+    end
+
+    assert_equal <<~MSG.chomp, e.detailed_message(highlight: false)
+      Unknown command upgrade (Gem::UnknownCommandError)
+      Please use `bundle update <gem_name>` to update gems in your bundle.
+    MSG
+
+    def e.can_display_colors? = true
+
+    assert_equal <<~MSG.chomp, e.detailed_message(highlight: true)
+      \e[1mUnknown command upgrade (\e[1;4mGem::UnknownCommandError\e[m\e[1m)\e[m
+      Please use \e[1m\e[36mbundle update <gem_name>\e[0m to update gems in your bundle.
+    MSG
+  end
+
   def test_run_interrupt
     old_load_path = $:.dup
     $: << File.expand_path("test/rubygems", PROJECT_DIR)