diff --git a/Library/Homebrew/blacklist.rb b/Library/Homebrew/blacklist.rb
index 4312d0bf3b..1c79da1593 100644
--- a/Library/Homebrew/blacklist.rb
+++ b/Library/Homebrew/blacklist.rb
@@ -16,7 +16,7 @@ def blacklisted?(name)
     Homebrew provides pip via: `brew install python`. However you will then
     have two Pythons installed on your Mac, so alternatively you can install
     pip via the instructions at:
-      https://pip.readthedocs.io/en/stable/installing/
+      #{Formatter.url("https://pip.readthedocs.io/en/stable/installing/")}
     EOS
   when "pil" then <<-EOS.undent
     Instead of PIL, consider `pip install pillow` or `brew install Homebrew/python/pillow`.
@@ -24,7 +24,7 @@ def blacklisted?(name)
   when "macruby" then <<-EOS.undent
     MacRuby is not packaged and is on an indefinite development hiatus.
     You can read more about it at:
-      https://github.com/MacRuby/MacRuby
+      #{Formatter.url("https://github.com/MacRuby/MacRuby")}
     EOS
   when /(lib)?lzma/
     "lzma is now part of the xz formula."
@@ -50,7 +50,7 @@ def blacklisted?(name)
     To install Clojure you should install Leiningen:
       brew install leiningen
     and then follow the tutorial:
-      https://github.com/technomancy/leiningen/blob/stable/doc/TUTORIAL.md
+      #{Formatter.url("https://github.com/technomancy/leiningen/blob/stable/doc/TUTORIAL.md")}
     EOS
   when "osmium" then <<-EOS.undent
     The creator of Osmium requests that it not be packaged and that people
@@ -65,8 +65,8 @@ def blacklisted?(name)
       brew install typesafe-activator
 
     You can read more about this change at:
-      https://www.playframework.com/documentation/2.3.x/Migration23
-      https://www.playframework.com/documentation/2.3.x/Highlights23
+      #{Formatter.url("https://www.playframework.com/documentation/2.3.x/Migration23")}
+      #{Formatter.url("https://www.playframework.com/documentation/2.3.x/Highlights23")}
     EOS
   when "haskell-platform" then <<-EOS.undent
     We no longer package haskell-platform. Consider installing ghc
diff --git a/Library/Homebrew/cask/lib/hbc/dsl/caveats.rb b/Library/Homebrew/cask/lib/hbc/dsl/caveats.rb
index 5efd7d5621..9dd9abab1c 100644
--- a/Library/Homebrew/cask/lib/hbc/dsl/caveats.rb
+++ b/Library/Homebrew/cask/lib/hbc/dsl/caveats.rb
@@ -102,12 +102,12 @@ module Hbc
 
         A report has been made to Apple about this app. Their certificate will hopefully be revoked.
         See the public report at
-          https://openradar.appspot.com/#{radar_number}
+          #{Formatter.url("https://openradar.appspot.com/#{radar_number}")}
 
         If this report is accurate, please duplicate it at
-          https://bugreport.apple.com/
+          #{Formatter.url("https://bugreport.apple.com/")}
         If this report is a mistake, please let us know by opening an issue at
-          https://github.com/caskroom/homebrew-cask/issues/new
+          #{Formatter.url("https://github.com/caskroom/homebrew-cask/issues/new")}
 
         EOS
       end
diff --git a/Library/Homebrew/cmd/help.rb b/Library/Homebrew/cmd/help.rb
index 05a3003cc8..c8845b086e 100644
--- a/Library/Homebrew/cmd/help.rb
+++ b/Library/Homebrew/cmd/help.rb
@@ -78,11 +78,12 @@ module Homebrew
       HOMEBREW_HELP
     else
       help_lines.map do |line|
-        line.slice(2..-1).
-          sub(/^  \* /, "#{Tty.bold}brew#{Tty.reset} ").
-          gsub(/`(.*?)`/, "#{Tty.bold}\\1#{Tty.reset}").
-          gsub(/<(.*?)>/, "#{Tty.underline}\\1#{Tty.reset}").
-          gsub("@hide_from_man_page", "")
+        line.slice(2..-1)
+            .sub(/^  \* /, "#{Tty.bold}brew#{Tty.reset} ")
+            .gsub(/`(.*?)`/, "#{Tty.bold}\\1#{Tty.reset}")
+            .gsub(%r{<([^\s]+?://[^\s]+?)>}) { |url| Formatter.url(url) }
+            .gsub(/<(.*?)>/, "#{Tty.underline}\\1#{Tty.reset}")
+            .gsub("@hide_from_man_page", "")
       end.join.strip
     end
   end
diff --git a/Library/Homebrew/cmd/update-report.rb b/Library/Homebrew/cmd/update-report.rb
index c275606e28..f97191bdaf 100644
--- a/Library/Homebrew/cmd/update-report.rb
+++ b/Library/Homebrew/cmd/update-report.rb
@@ -288,7 +288,7 @@ module Homebrew
       Please try to resolve this error yourself and then run `brew update` again to
       complete the migration. If you need help please +1 an existing error or comment
       with your new error in issue:
-        #{Tty.em}https://github.com/Homebrew/brew/issues/987#{Tty.reset}
+        #{Formatter.url("https://github.com/Homebrew/brew/issues/987")}
     EOS
     $stderr.puts e.backtrace
   end
diff --git a/Library/Homebrew/diagnostic.rb b/Library/Homebrew/diagnostic.rb
index ca8ade9ff8..6546714e87 100644
--- a/Library/Homebrew/diagnostic.rb
+++ b/Library/Homebrew/diagnostic.rb
@@ -473,7 +473,7 @@ module Homebrew
           If you have trouble downloading packages with Homebrew, then maybe this
           is the problem? If the following command doesn't work, then try removing
           your curlrc:
-            curl https://github.com
+            curl #{Formatter.url("https://github.com")}
         EOS
       end
 
@@ -610,7 +610,7 @@ module Homebrew
 
             Setting DYLD_INSERT_LIBRARIES can cause Go builds to fail.
             Having this set is common if you use this software:
-              http://asepsis.binaryage.com/
+              #{Formatter.url("http://asepsis.binaryage.com/")}
           EOS
         end
 
@@ -752,7 +752,7 @@ module Homebrew
             Without a correctly configured origin, Homebrew won't update
             properly. You can solve this by adding the Homebrew remote:
               cd #{HOMEBREW_REPOSITORY}
-              git remote add origin https://github.com/Homebrew/brew.git
+              git remote add origin #{Formatter.url("https://github.com/Homebrew/brew.git")}
           EOS
         elsif origin !~ %r{Homebrew/brew(\.git)?$}
           <<-EOS.undent
@@ -764,7 +764,7 @@ module Homebrew
 
             Unless you have compelling reasons, consider setting the
             origin remote to point at the main repository, located at:
-              https://github.com/Homebrew/brew.git
+              #{Formatter.url("https://github.com/Homebrew/brew.git")}
           EOS
         end
       end
@@ -956,8 +956,8 @@ module Homebrew
         <<-EOS.undent
           A .pydistutils.cfg file was found in $HOME, which may cause Python
           builds to fail. See:
-            https://bugs.python.org/issue6138
-            https://bugs.python.org/issue4655
+            #{Formatter.url("https://bugs.python.org/issue6138")}
+            #{Formatter.url("https://bugs.python.org/issue4655")}
         EOS
       end
 
diff --git a/Library/Homebrew/exceptions.rb b/Library/Homebrew/exceptions.rb
index 601bde5285..e01a60c758 100644
--- a/Library/Homebrew/exceptions.rb
+++ b/Library/Homebrew/exceptions.rb
@@ -318,7 +318,7 @@ class BuildError < RuntimeError
   def dump
     if !ARGV.verbose?
       puts
-      puts Formatter.error("READ THIS: #{Formatter.url(OS::ISSUES_URL)}")
+      puts Formatter.error(Formatter.url(OS::ISSUES_URL), label: "READ THIS")
       if formula.tap
         case formula.tap.name
         when "homebrew/boneyard"
@@ -327,7 +327,7 @@ class BuildError < RuntimeError
         else
           if issues_url = formula.tap.issues_url
             puts "If reporting this issue please do so at (not Homebrew/brew):"
-            puts "  #{issues_url}"
+            puts "  #{Formatter.url(issues_url)}"
           end
         end
       end
diff --git a/Library/Homebrew/requirements.rb b/Library/Homebrew/requirements.rb
index 274ba5c9b8..87b315cb76 100644
--- a/Library/Homebrew/requirements.rb
+++ b/Library/Homebrew/requirements.rb
@@ -44,7 +44,7 @@ class XcodeRequirement < Requirement
       EOS
     else
       message + <<-EOS.undent
-        Xcode can be installed from https://developer.apple.com/xcode/downloads/
+        Xcode can be installed from #{Formatter.url("https://developer.apple.com/xcode/downloads/")}
       EOS
     end
   end
diff --git a/Library/Homebrew/utils/github.rb b/Library/Homebrew/utils/github.rb
index 1443a93361..5611f9aadd 100644
--- a/Library/Homebrew/utils/github.rb
+++ b/Library/Homebrew/utils/github.rb
@@ -106,14 +106,14 @@ module GitHub
           onoe <<-EOS.undent
             Your macOS keychain GitHub credentials do not have sufficient scope!
             Scopes they have: #{credentials_scopes}
-            Create a personal access token: https://github.com/settings/tokens
+            Create a personal access token: #{Formatter.url("https://github.com/settings/tokens")}
             and then set HOMEBREW_GITHUB_API_TOKEN as the authentication method instead.
           EOS
         when :environment
           onoe <<-EOS.undent
             Your HOMEBREW_GITHUB_API_TOKEN does not have sufficient scope!
             Scopes it has: #{credentials_scopes}
-            Create a new personal access token: https://github.com/settings/tokens
+            Create a new personal access token: #{Formatter.url("https://github.com/settings/tokens")}
             and then set the new HOMEBREW_GITHUB_API_TOKEN as the authentication method instead.
           EOS
         end