diff --git a/Library/Homebrew/cli_parser.rb b/Library/Homebrew/cli_parser.rb
index 17b21cdca7..844bc9130c 100644
--- a/Library/Homebrew/cli_parser.rb
+++ b/Library/Homebrew/cli_parser.rb
@@ -28,13 +28,13 @@ module Homebrew
         @constraints = []
         @conflicts = []
         @processed_options = []
-        @desc_line_length = 48
+        @desc_line_length = 43
         instance_eval(&block)
         post_initialize
       end
 
       def post_initialize
-        @parser.on_tail("-h", "--help", "Show this message") do
+        @parser.on_tail("-h", "--help", "Show this message.") do
           puts generate_help_text
           exit 0
         end
@@ -127,9 +127,10 @@ module Homebrew
 
       def generate_help_text
         @parser.to_s.sub(/^/, "#{Tty.bold}Usage: brew#{Tty.reset} ")
-               .gsub(/`(.*?)`/, "#{Tty.bold}\\1#{Tty.reset}")
+               .gsub(/`(.*?)`/m, "#{Tty.bold}\\1#{Tty.reset}")
                .gsub(%r{<([^\s]+?://[^\s]+?)>}) { |url| Formatter.url(url) }
-               .gsub(/<(.*?)>/, "#{Tty.underline}\\1#{Tty.reset}")
+               .gsub(/<(.*?)>/m, "#{Tty.underline}\\1#{Tty.reset}")
+               .gsub(/\*(.*?)\*/m, "#{Tty.underline}\\1#{Tty.reset}")
       end
 
       private
diff --git a/Library/Homebrew/help.rb b/Library/Homebrew/help.rb
index d541081c8d..671a962afc 100644
--- a/Library/Homebrew/help.rb
+++ b/Library/Homebrew/help.rb
@@ -93,6 +93,7 @@ module Homebrew
               .gsub(/`(.*?)`/, "#{Tty.bold}\\1#{Tty.reset}")
               .gsub(%r{<([^\s]+?://[^\s]+?)>}) { |url| Formatter.url(url) }
               .gsub(/<(.*?)>/, "#{Tty.underline}\\1#{Tty.reset}")
+              .gsub(/\*(.*?)\*/, "#{Tty.underline}\\1#{Tty.reset}")
               .gsub("@hide_from_man_page", "")
         end.join.strip
       end
diff --git a/Library/Homebrew/test/cli_parser_spec.rb b/Library/Homebrew/test/cli_parser_spec.rb
index ba1f8c4ae8..a2f294e78e 100644
--- a/Library/Homebrew/test/cli_parser_spec.rb
+++ b/Library/Homebrew/test/cli_parser_spec.rb
@@ -89,6 +89,7 @@ describe Homebrew::CLI::Parser do
 
     it "raises exception on depends_on constraint violation" do
       expect { parser.parse(["--flag2=flag2"]) }.to raise_error(Homebrew::CLI::OptionConstraintError)
+      expect { parser.parse(["--flag4=flag4"]) }.to raise_error(Homebrew::CLI::OptionConstraintError)
     end
 
     it "raises exception for conflict violation" do
@@ -139,6 +140,7 @@ describe Homebrew::CLI::Parser do
 
     it "raises exception on depends_on constraint violation" do
       expect { parser.parse(["--switch-c"]) }.to raise_error(Homebrew::CLI::OptionConstraintError)
+      expect { parser.parse(["--switch-d"]) }.to raise_error(Homebrew::CLI::OptionConstraintError)
     end
 
     it "raises exception for conflict violation" do