diff --git a/lib/Rex/Commands/Sync.pm b/lib/Rex/Commands/Sync.pm
index 0d937dfd3..eb4714440 100644
--- a/lib/Rex/Commands/Sync.pm
+++ b/lib/Rex/Commands/Sync.pm
@@ -94,70 +94,54 @@ sub sync_up {
   $source = get_file_path( $source, caller );
 
   #
-  # first, get all files on source side
+  # first, build excludes list
   #
-  my @local_files = _get_local_files($source);
 
-  #print Dumper(\@local_files);
+  my $excludes = $options->{exclude} ||= [];
+  $excludes = [$excludes] unless ref($excludes) eq 'ARRAY';
 
-  #
-  # second, get all files from destination side
-  #
+  my @excluded_files = @{$excludes};
 
-  my @remote_files = _get_remote_files($dest);
+  my $check_exclude_file = sub {
+    my ($file) = @_;
+    $file =~ s{^/}{};
 
-  #print Dumper(\@remote_files);
+    for my $cmp (@excluded_files) {
+      return 1 if match_glob( $cmp, $file );
+    }
+
+    return 0;
+  };
 
   #
-  # third, get the difference
+  # second, get all files on source side (minus excludes)
   #
+  my @local_files = _get_local_files( $source, $check_exclude_file );
 
-  my @diff = _diff_files( \@local_files, \@remote_files );
-
-  #print Dumper(\@diff);
+  #print Dumper(\@local_files);
 
   #
-  # fourth, build excludes list
+  # third, get all files from destination side (minus excludes)
   #
 
-  my $excludes = $options->{exclude} ||= [];
-  $excludes = [$excludes] unless ref($excludes) eq 'ARRAY';
+  my @remote_files = _get_remote_files( $dest, $check_exclude_file );
 
-  my @excluded_files = @{$excludes};
+  #print Dumper(\@remote_files);
 
   #
-  # fifth, upload the different files
+  # fourth, get the difference
   #
 
-  my $check_exclude_file = sub {
-    my ( $file, $cmp ) = @_;
-    if ( $cmp =~ m/\// ) {
-
-      # this is a directory exclude
-      if ( match_glob( $cmp, $file ) || match_glob( $cmp, substr( $file, 1 ) ) )
-      {
-        return 1;
-      }
-
-      return 0;
-    }
+  my @diff = _diff_files( \@local_files, \@remote_files );
 
-    if ( match_glob( $cmp, basename($file) ) ) {
-      return 1;
-    }
+  #print Dumper(\@diff);
 
-    return 0;
-  };
+  #
+  # fifth, upload the different files
+  #
 
   my @uploaded_files;
   for my $file (@diff) {
-    next
-      if (
-      scalar(
-        grep { $check_exclude_file->( $file->{name}, $_ ) } @excluded_files
-      ) > 0
-      );
-
     my ($dir)        = ( $file->{path} =~ m/(.*)\/[^\/]+$/ );
     my ($remote_dir) = ( $file->{name} =~ m/\/(.*)\/[^\/]+$/ );
 
@@ -252,44 +236,53 @@ sub sync_down {
   $dest   = resolv_path($dest);
 
   #
-  # first, get all files on dest side
+  # first, build excludes list
   #
-  my @local_files = _get_local_files($dest);
 
-  #print Dumper(\@local_files);
+  my $excludes = $options->{exclude} ||= [];
+  $excludes = [$excludes] unless ref($excludes) eq 'ARRAY';
+
+  my @excluded_files = @{$excludes};
+
+  my $check_exclude_file = sub {
+    my ($file) = @_;
+    $file =~ s{^/}{};
+
+    for my $cmp (@excluded_files) {
+      return 1 if match_glob( $cmp, $file );
+    }
+
+    return 0;
+  };
 
   #
-  # second, get all files from source side
+  # second, get all files on dest side (minus excludes)
   #
+  my @local_files = _get_local_files( $dest, $check_exclude_file );
 
-  my @remote_files = _get_remote_files($source);
-
-  #print Dumper(\@remote_files);
+  #print Dumper(\@local_files);
 
   #
-  # third, get the difference
+  # third, get all files from source side (minus excludes)
   #
 
-  my @diff = _diff_files( \@remote_files, \@local_files );
+  my @remote_files = _get_remote_files( $source, $check_exclude_file );
 
-  #print Dumper(\@diff);
+  #print Dumper(\@remote_files);
 
   #
-  # fourth, build excludes list
+  # fourth, get the difference
   #
 
-  my $excludes = $options->{exclude} ||= [];
-  $excludes = [$excludes] unless ref($excludes) eq 'ARRAY';
+  my @diff = _diff_files( \@remote_files, \@local_files );
 
-  my @excluded_files = map { glob_to_regex($_); } @{$excludes};
+  #print Dumper(\@diff);
 
   #
   # fifth, download the different files
   #
 
   for my $file (@diff) {
-    next if grep { basename( $file->{name} ) =~ $_ } @excluded_files;
-
     my ($dir)        = ( $file->{path} =~ m/(.*)\/[^\/]+$/ );
     my ($remote_dir) = ( $file->{name} =~ m/\/(.*)\/[^\/]+$/ );
 
@@ -326,7 +319,7 @@ sub sync_down {
 }
 
 sub _get_local_files {
-  my ($source) = @_;
+  my ( $source, $exclude_sub ) = @_;
 
   if ( !-d $source ) { die("$source : no such directory."); }
 
@@ -337,13 +330,15 @@ sub _get_local_files {
       for my $entry ( list_files($dir) ) {
         next if ( $entry eq "." );
         next if ( $entry eq ".." );
+
+        my $name = "$dir/$entry";
+        $name =~ s/^\Q$source\E//;
+        next if $exclude_sub->($name);
+
         if ( is_dir("$dir/$entry") ) {
           push( @dirs, "$dir/$entry" );
           next;
         }
-
-        my $name = "$dir/$entry";
-        $name =~ s/^\Q$source\E//;
         push(
           @local_files,
           {
@@ -361,7 +356,7 @@ sub _get_local_files {
 }
 
 sub _get_remote_files {
-  my ($dest) = @_;
+  my ( $dest, $exclude_sub ) = @_;
 
   if ( !is_dir($dest) ) { die("$dest : no such directory."); }
 
@@ -372,13 +367,16 @@ sub _get_remote_files {
     for my $entry ( list_files($dir) ) {
       next if ( $entry eq "." );
       next if ( $entry eq ".." );
+
+      my $name = "$dir/$entry";
+      $name =~ s/^\Q$dest\E//;
+      next if $exclude_sub->($name);
+
       if ( is_dir("$dir/$entry") ) {
         push( @remote_dirs, "$dir/$entry" );
         next;
       }
 
-      my $name = "$dir/$entry";
-      $name =~ s/^\Q$dest\E//;
       push(
         @remote_files,
         {
@@ -411,3 +409,4 @@ sub _diff_files {
 }
 
 1;
+
diff --git a/t/sync.t b/t/sync.t
new file mode 100755
index 000000000..e1f6151eb
--- /dev/null
+++ b/t/sync.t
@@ -0,0 +1,132 @@
+#!/usr/bin/env perl
+
+use v5.12.5;
+use warnings;
+
+use Test::More;
+
+our $VERSION = '9999.99.99_99'; # VERSION
+use autodie;
+
+use File::Find;
+use File::Temp qw(tempdir);
+use Rex::Task;
+use Rex::Commands::Sync;
+use Test::Deep;
+
+subtest 'should sync_up' => sub {
+  my $source = 't/sync';
+  my $target = prepare_directory();
+
+  run_task(
+    sub {
+      sync_up $source, $target;
+    }
+  );
+
+  compare_contents( $source, $target );
+};
+
+subtest 'should sync_up with excludes' => sub {
+  my $source = 't/sync';
+  my $target = prepare_directory();
+
+  # NOTE: file4 should not be excluded, as it is nested
+  run_task(
+    sub {
+      sync_up $source, $target,
+        { exclude => [ 'dir/file2', 'file4', 'dir with spaces' ] };
+    }
+  );
+
+  compare_contents( $source, $target,
+    [ '/dir/file2', '/dir with spaces', '/dir with spaces/file3' ] );
+};
+
+subtest 'should sync_down' => sub {
+  my $source = 't/sync';
+  my $target = prepare_directory();
+
+  run_task(
+    sub {
+      sync_down $source, $target;
+    }
+  );
+
+  compare_contents( $source, $target );
+};
+
+subtest 'should sync_down with excludes' => sub {
+  my $source = 't/sync';
+  my $target = prepare_directory();
+
+  # NOTE: file4 should not be excluded, as it is nested
+  run_task(
+    sub {
+      sync_down $source, $target,
+        { exclude => [ 'dir/file2', 'file4', 'dir with spaces' ] };
+    }
+  );
+
+  compare_contents( $source, $target,
+    [ '/dir/file2', '/dir with spaces', '/dir with spaces/file3' ] );
+};
+
+sub prepare_directory {
+  my $target = tempdir( CLEANUP => 1 );
+  die unless -d $target;
+
+  return $target;
+}
+
+sub run_task {
+  my ($func) = @_;
+
+  my $task = Rex::Task->new(
+    name => 'sync_test',
+    func => $func,
+  );
+
+  $task->run('<local>');
+}
+
+sub compare_contents {
+  my ( $source, $target, $excluded ) = @_;
+  $excluded //= [];
+  my %excluded_map = map { $_ => 1 } @{$excluded};
+
+  # test sync results
+  my ( @expected, @result );
+
+  # expected results
+  find(
+    {
+      wanted => sub {
+        s/$source//;
+        return unless length;
+        return if $excluded_map{$_};
+        push @expected, $_;
+      },
+      no_chdir => 1
+    },
+    $source
+  );
+
+  # actual results
+  find(
+    {
+      wanted => sub {
+        s/$target//;
+        return unless length;
+        push @result, $_;
+      },
+      no_chdir => 1
+    },
+    $target
+  );
+
+  cmp_deeply( \@result, set(@expected), 'synced dir matches' );
+}
+
+done_testing;
+
diff --git a/t/sync/dir/file4 b/t/sync/dir/file4
new file mode 100644
index 000000000..e69de29bb