diff --git a/libraries/manipulator.rb b/libraries/manipulator.rb
index a51d9b1d..aef9f41e 100644
--- a/libraries/manipulator.rb
+++ b/libraries/manipulator.rb
@@ -102,7 +102,7 @@ def update(options = {})
   #
   # @param (see #add)
   def append(options = {})
-    if entry = find_entry_by_ip_address(options[:ip_address])
+    if entry = not(node['platform_family'] == 'windows') && find_entry_by_ip_address(options[:ip_address])
       hosts          = normalize(entry.hostname, entry.aliases, options[:hostname], options[:aliases])
       entry.hostname = hosts.shift
       entry.aliases  = hosts
@@ -217,7 +217,14 @@ def new_content
     entries = hostsfile_header
     entries += unique_entries.map(&:to_line)
     entries << ''
-    entries.join("\n")
+    # windows has a limit of 9 host aliases per line, so without proper line
+    # endings, additional host entries wind up being ignored
+    case node['platform_family']
+      when 'windows'
+        entries.join("\r\n")
+      else
+        entries.join("\n")
+      end
   end
 
   # The current sha of the system hostsfile.
@@ -244,7 +251,8 @@ def normalize(*things)
   # @return [Array]
   #   the sorted list of entires that are unique
   def unique_entries
-    entries = Hash[*@entries.map { |entry| [entry.ip_address, entry] }.flatten].values
+    is_windows = node['platform_family'] == 'windows'
+    entries = Hash[*@entries.map { |entry| [is_windows ? entry.hostname : entry.ip_address, entry] }.flatten].values
     entries.sort_by { |e| [-e.priority.to_i, e.hostname.to_s] }
   end