diff --git a/libraries/entry.rb b/libraries/entry.rb
index 57ddf7b9..2315feeb 100644
--- a/libraries/entry.rb
+++ b/libraries/entry.rb
@@ -136,14 +136,36 @@ def priority=(new_priority)
     # @return [String]
     #   the string representation of this entry
     def to_line
-      hosts = [hostname, aliases].flatten.join(' ')
+      hosts = [hostname, aliases].flatten
+
+      # Windows only allows 9 hostname entries per line
+      # It does support multiple lines for an ip to cover that
+      if Chef::Platform.windows? && hosts.size > 9
+        comments = entry_comment(comment, priority)
+        results = []
+        until hosts.empty?
+          hosts_set = hosts[0..8].join(' ')
+          hosts = hosts[9..-1] || []
+          results << [ip_address, hosts_set, comments].compact.join("\t").strip
+        end
+        results.join("\n")
+      else
+        hosts = hosts.join(' ')
+        comments = entry_comment(comment, priority)
+
+        [ip_address, hosts, comments].compact.join("\t").strip
+      end
+    end
 
+    # Returns formatted comments of a entry
+    #
+    # @return [String]
+    def entry_comment(comment, priority)
       comments = "# #{comment}".strip
       comments << " @#{priority}" unless priority.nil? || @calculated_priority
       comments = comments.strip
       comments = nil if comments == '#'
-
-      [ip_address, hosts, comments].compact.join("\t").strip
+      comments
     end
 
     # Returns true if priority is calculated
diff --git a/spec/unit/entry_spec.rb b/spec/unit/entry_spec.rb
index 2111ddad..1f9ac618 100644
--- a/spec/unit/entry_spec.rb
+++ b/spec/unit/entry_spec.rb
@@ -164,5 +164,79 @@
         expect(subject.to_line).to eq("2.3.4.5\twww.example.com\t# This is a comment! @10")
       end
     end
+
+    context 'windows' do
+      subject { HostsFile::Entry.new(ip_address: '2.3.4.5', hostname: 'www.example.com', comment: 'This is a comment!', priority: 10) }
+
+      before do
+        allow(Chef::Platform).to receive(:windows?).and_return(true)
+      end
+
+      it 'prints 9 hosts on a single line' do
+        subject.aliases = ['www.example2.com',
+                           'www.example3.com',
+                           'www.example4.com',
+                           'www.example5.com',
+                           'www.example6.com',
+                           'www.example7.com',
+                           'www.example8.com',
+                           'www.example9.com']
+
+        expect(subject.to_line).to eq("2.3.4.5\twww.example.com www.example2.com www.example3.com www.example4.com www.example5.com www.example6.com www.example7.com www.example8.com www.example9.com\t# This is a comment! @10")
+      end
+
+      it 'prints more than 9 hosts on multiple lines' do
+        subject.aliases = ['www.example2.com',
+                           'www.example3.com',
+                           'www.example4.com',
+                           'www.example5.com',
+                           'www.example6.com',
+                           'www.example7.com',
+                           'www.example8.com',
+                           'www.example9.com',
+                           'www.example10.com',
+                           'www.example11.com',
+                           'www.example12.com']
+
+        expect(subject.to_line).to eq("2.3.4.5\twww.example.com www.example2.com www.example3.com www.example4.com www.example5.com www.example6.com www.example7.com www.example8.com www.example9.com\t# This is a comment! @10\n2.3.4.5\twww.example10.com www.example11.com www.example12.com\t# This is a comment! @10")
+      end
+    end
+
+    context 'linux' do
+      subject { HostsFile::Entry.new(ip_address: '2.3.4.5', hostname: 'www.example.com', comment: 'This is a comment!', priority: 10) }
+
+      before do
+        allow(Chef::Platform).to receive(:windows?).and_return(false)
+      end
+
+      it 'prints 9 hosts on a single line' do
+        subject.aliases = ['www.example2.com',
+                           'www.example3.com',
+                           'www.example4.com',
+                           'www.example5.com',
+                           'www.example6.com',
+                           'www.example7.com',
+                           'www.example8.com',
+                           'www.example9.com']
+
+        expect(subject.to_line).to eq("2.3.4.5\twww.example.com www.example2.com www.example3.com www.example4.com www.example5.com www.example6.com www.example7.com www.example8.com www.example9.com\t# This is a comment! @10")
+      end
+
+      it 'prints more than 9 hosts on a single line' do
+        subject.aliases = ['www.example2.com',
+                           'www.example3.com',
+                           'www.example4.com',
+                           'www.example5.com',
+                           'www.example6.com',
+                           'www.example7.com',
+                           'www.example8.com',
+                           'www.example9.com',
+                           'www.example10.com',
+                           'www.example11.com',
+                           'www.example12.com']
+
+        expect(subject.to_line).to eq("2.3.4.5\twww.example.com www.example2.com www.example3.com www.example4.com www.example5.com www.example6.com www.example7.com www.example8.com www.example9.com www.example10.com www.example11.com www.example12.com\t# This is a comment! @10")
+      end
+    end
   end
 end