diff --git a/plugins/synced_folders/rsync/helper.rb b/plugins/synced_folders/rsync/helper.rb
index c99a9dff2..6ee1dea92 100644
--- a/plugins/synced_folders/rsync/helper.rb
+++ b/plugins/synced_folders/rsync/helper.rb
@@ -27,18 +27,15 @@ module VagrantPlugins
 
         if exclude.start_with?("/")
           start_anchor = true
-          exclude      = exclude[1..-1]
         end
 
-        exclude = "#{exclude}/" if !exclude.end_with?("/")
-        exclude = "^#{exclude}"
-        exclude += ".*" if !start_anchor
+        exclude = "#{exclude}/" if !exclude.end_with?("/") if start_anchor
+        exclude = "^#{exclude}" if start_anchor
+        exclude += ".*" if (!start_anchor && !exclude.end_with?("*"))
 
         # This is not an ideal solution, but it's a start. We can improve and
         # keep unit tests passing in the future.
         exclude = exclude.gsub("**", "|||GLOBAL|||")
-        exclude = exclude.gsub("*", "|||PATH|||")
-        exclude = exclude.gsub("|||PATH|||", "[^/]*")
         exclude = exclude.gsub("|||GLOBAL|||", ".*")
 
         Regexp.new(exclude)
diff --git a/test/unit/plugins/synced_folders/rsync/helper_test.rb b/test/unit/plugins/synced_folders/rsync/helper_test.rb
index 67472f384..44c3d30bd 100644
--- a/test/unit/plugins/synced_folders/rsync/helper_test.rb
+++ b/test/unit/plugins/synced_folders/rsync/helper_test.rb
@@ -32,23 +32,31 @@ describe VagrantPlugins::SyncedFolderRSync::RsyncHelper do
     let(:path) { "/foo/bar" }
 
     it "converts a directory match" do
+      expected_regex = /foo\/.*/
       expect(described_class.exclude_to_regexp("foo/")).
-        to eq(/^foo\/.[^\/]*/)
+        to eq(/foo\/.*/)
+      expect(path).to match(expected_regex)
     end
 
     it "converts the start anchor" do
+      expected_regex = /^\/foo\//
       expect(described_class.exclude_to_regexp("/foo")).
-        to eq(/^foo\//)
+        to eq(expected_regex)
+      expect(path).to match(expected_regex)
     end
 
     it "converts the **" do
+      expected_regex = /fo.*o.*/
       expect(described_class.exclude_to_regexp("fo**o")).
-        to eq(/^fo.*o\/.[^\/]*/)
+        to eq(expected_regex)
+      expect(path).to match(expected_regex)
     end
 
     it "converts the *" do
+      expected_regex = /fo*o.*/
       expect(described_class.exclude_to_regexp("fo*o")).
-        to eq(/^fo[^\/]*o\/.[^\/]*/)
+        to eq(expected_regex)
+      expect(path).to match(expected_regex)
     end
   end