diff --git a/Library/Homebrew/cmd/link.rb b/Library/Homebrew/cmd/link.rb
index d882ee7ec6..09d16c7824 100644
--- a/Library/Homebrew/cmd/link.rb
+++ b/Library/Homebrew/cmd/link.rb
@@ -1,4 +1,5 @@
 module Homebrew extend self
+
   def link
     raise KegUnspecifiedError if ARGV.named.empty?
 
@@ -9,9 +10,30 @@ module Homebrew extend self
     end
 
     ARGV.kegs.each do |keg|
-      print "Linking #{keg}... "
-      puts if ARGV.verbose?
-      puts "#{keg.link} symlinks created"
+      print "Linking #{keg}... " do
+        puts if ARGV.verbose?
+        puts "#{keg.link} symlinks created"
+      end
     end
   end
+
+  private
+
+  # Allows us to ensure a puts happens before the block exits so that if say,
+  # an exception is thrown, its output starts on a new line.
+  def print str, &block
+    Kernel.print str
+    puts_capture = Class.new do
+      def self.puts str
+        $did_puts = true
+        Kernel.puts str
+      end
+    end
+
+    puts_capture.instance_eval &block
+
+  ensure
+    puts unless $did_puts
+  end
+
 end
diff --git a/Library/Homebrew/extend/pathname.rb b/Library/Homebrew/extend/pathname.rb
index 1ccbff51cf..7412fd157c 100644
--- a/Library/Homebrew/extend/pathname.rb
+++ b/Library/Homebrew/extend/pathname.rb
@@ -283,9 +283,14 @@ class Pathname
     self.dirname.mkpath
     Dir.chdir self.dirname do
       # NOTE only system ln -s will create RELATIVE symlinks
-      system 'ln', '-s', src.relative_path_from(self.dirname), self.basename
-      # ln outputs useful error message for us
-      raise "Could not create symlink: #{to_s}." unless $?.success?
+      quiet_system 'ln', '-s', src.relative_path_from(self.dirname), self.basename
+      if not $?.success?
+        raise <<-EOS.undent
+          Could not symlink file: #{src.expand_path}
+          Check #{self} does not already exist.
+          Check #{dirname} is writable.
+        EOS
+      end
     end
   end