diff --git a/lib/jekyll/entry_filter.rb b/lib/jekyll/entry_filter.rb
index 48509f9d..cfbbc1f1 100644
--- a/lib/jekyll/entry_filter.rb
+++ b/lib/jekyll/entry_filter.rb
@@ -52,7 +52,11 @@ module Jekyll
     end
 
     def symlink?(entry)
-      File.symlink?(entry) && site.safe
+      site.safe && File.symlink?(entry) && bad_symlink?(entry)
+    end
+
+    def bad_symlink?(entry)
+      ! File.realpath(entry).start_with?(File.realpath(@site.source))
     end
 
     def ensure_leading_slash(path)
diff --git a/test/test_entry_filter.rb b/test/test_entry_filter.rb
index 546f0252..8887d43b 100644
--- a/test/test_entry_filter.rb
+++ b/test/test_entry_filter.rb
@@ -46,11 +46,11 @@ class TestEntryFilter < JekyllUnitTest
       assert_equal files, @site.reader.filter_entries(files)
     end
 
-    should "filter symlink entries when safe mode enabled" do
+    should "keep safe symlink entries when safe mode enabled" do
       site = Site.new(site_configuration('safe' => true))
       allow(File).to receive(:symlink?).with('symlink.js').and_return(true)
       files = %w[symlink.js]
-      assert_equal [], site.reader.filter_entries(files)
+      assert_equal files, @site.reader.filter_entries(files)
     end
 
     should "not filter symlink entries when safe mode disabled" do
@@ -59,12 +59,12 @@ class TestEntryFilter < JekyllUnitTest
       assert_equal files, @site.reader.filter_entries(files)
     end
 
-    should "not include symlinks in safe mode" do
+    should "include only safe symlinks in safe mode" do
       site = Site.new(site_configuration('safe' => true))
 
       site.reader.read_directories("symlink-test")
-      assert_equal [], site.pages
-      assert_equal [], site.static_files
+      assert_equal %w[main.scss symlinked-file].length, site.pages.length
+      refute_equal [], site.static_files
     end
 
     should "include symlinks in unsafe mode" do