diff --git a/lib/rex/file.rb b/lib/rex/file.rb
index 2c04765bb5..51337657da 100644
--- a/lib/rex/file.rb
+++ b/lib/rex/file.rb
@@ -35,14 +35,14 @@ module FileUtils
 		# Filter out double slashes
 		s = s.gsub(/\\\\/, '\\') while s.index('\\\\')
 
+		# Keep the trailing slash if exists
+		trailing_s = ('\\' if s =~ /\\$/) || ''
+
 		# Check the items (fie/dir) individually
 		s = s.split(/\\/)
 
 		# Parse the path prefix
 		prefix = (s[0] || '').gsub(/[\*<>\?\/]/, '')
-		if prefix =~ /^\w:$/ and s.length == 1
-			prefix += '\\'
-		end
 
 		# Delete the original prefix. We want the new one later.
 		s.delete_at(0)
@@ -55,6 +55,9 @@ module FileUtils
 
 		# And then safely join the items
 		s *= '\\'
+
+		# Add the trailing slash back if exists
+		s << trailing_s
 	end
 
 	#
diff --git a/spec/lib/rex/file_utils_spec.rb b/spec/lib/rex/file_utils_spec.rb
index 7778a13b3b..e160cf95a5 100644
--- a/spec/lib/rex/file_utils_spec.rb
+++ b/spec/lib/rex/file_utils_spec.rb
@@ -17,6 +17,11 @@ describe Rex::FileUtils do
 				described_class.normalize_win_path('\\temp').should eq("\\temp")
 			end
 
+			it "should keep the trailing slash if exists" do
+				described_class.normalize_win_path('/', 'test', 'me\\').should eq("\\test\\me\\")
+				described_class.normalize_win_path('\\temp\\').should eq("\\temp\\")
+			end
+
 			it "should convert a path without reserved characters" do
 				described_class.normalize_win_path('C:\\', 'Windows:').should eq("C:\\Windows")
 				described_class.normalize_win_path('C:\\Windows???\\test').should eq("C:\\Windows\\test")
@@ -26,6 +31,7 @@ describe Rex::FileUtils do
 				described_class.normalize_win_path('C:\\\\\\', 'Windows').should eq("C:\\Windows")
 				described_class.normalize_win_path('C:\\\\\\Hello World\\\\whatever.txt').should eq("C:\\Hello World\\whatever.txt")
 				described_class.normalize_win_path('C:\\\\').should eq("C:\\")
+				described_class.normalize_win_path('\\test\\\\test\\\\').should eq("\\test\\test\\")
 			end
 		end