diff --git a/lib/fileutils.rb b/lib/fileutils.rb
index 37945b4096..adff31c944 100644
--- a/lib/fileutils.rb
+++ b/lib/fileutils.rb
@@ -412,7 +412,7 @@ def cp_r(src, dest, preserve: nil, noop: nil, verbose: nil,
   def copy_entry(src, dest, preserve = false, dereference_root = false, remove_destination = false)
     Entry_.new(src, nil, dereference_root).wrap_traverse(proc do |ent|
       destent = Entry_.new(dest, ent.rel, false)
-      File.unlink destent.path if remove_destination && File.file?(destent.path)
+      File.unlink destent.path if remove_destination && (File.file?(destent.path) || File.symlink?(destent.path))
       ent.copy destent.path
     end, proc do |ent|
       destent = Entry_.new(dest, ent.rel, false)
diff --git a/test/fileutils/test_fileutils.rb b/test/fileutils/test_fileutils.rb
index bc659c2a0a..35b5194b59 100644
--- a/test/fileutils/test_fileutils.rb
+++ b/test/fileutils/test_fileutils.rb
@@ -438,6 +438,15 @@ def test_cp_r_pathname
     }
   end
 
+  def test_cp_r_symlink_remove_destination
+    Dir.mkdir 'tmp/src'
+    Dir.mkdir 'tmp/dest'
+    Dir.mkdir 'tmp/src/dir'
+    File.symlink 'tmp/src/dir', 'tmp/src/a'
+    cp_r 'tmp/src', 'tmp/dest/', remove_destination: true
+    cp_r 'tmp/src', 'tmp/dest/', remove_destination: true
+  end
+
   def test_mv
     check_singleton :mv
 
@@ -1438,6 +1447,14 @@ def test_copy_entry_symlink
     assert_equal 'somewhere', File.readlink('tmp/dirdest/sym')
   end if have_symlink?
 
+  def test_copy_entry_symlink_remove_destination
+    Dir.mkdir 'tmp/dir'
+    File.symlink 'tmp/dir', 'tmp/dest'
+    touch 'tmp/src'
+    copy_entry 'tmp/src', 'tmp/dest', false, false, true
+    assert_file_exist 'tmp/dest'
+  end
+
   def test_copy_file
     check_singleton :copy_file