diff --git a/lib/bootsnap/load_path_cache/cache.rb b/lib/bootsnap/load_path_cache/cache.rb
index 837b72b2..12339da7 100644
--- a/lib/bootsnap/load_path_cache/cache.rb
+++ b/lib/bootsnap/load_path_cache/cache.rb
@@ -50,7 +50,7 @@ def find(feature, try_extensions: true)
 
         return feature if absolute_path?(feature)
 
-        if feature.start_with?('./')
+        if feature.start_with?('./') || feature.start_with?('../')
           return try_extensions ? expand_path(feature) : File.expand_path(feature).freeze
         end
 
diff --git a/test/load_path_cache/cache_test.rb b/test/load_path_cache/cache_test.rb
index bd862605..9b3a2c3b 100644
--- a/test/load_path_cache/cache_test.rb
+++ b/test/load_path_cache/cache_test.rb
@@ -58,9 +58,12 @@ def test_simple
       def test_extension_append_for_relative_paths
         po = [@dir1]
         cache = Cache.new(NullCache, po)
+        dir1_basename = File.basename(@dir1)
         Dir.chdir(@dir1) do
           assert_equal("#{@dir1}/a.rb",       cache.find('./a'))
           assert_equal("#{@dir1}/a",          cache.find('./a', try_extensions: false))
+          assert_equal("#{@dir1}/a.rb",       cache.find("../#{dir1_basename}/a"))
+          assert_equal("#{@dir1}/a",          cache.find("../#{dir1_basename}/a", try_extensions: false))
           assert_equal("#{@dir1}/dl#{DLEXT}", cache.find('./dl'))
           assert_equal("#{@dir1}/dl",         cache.find('./dl', try_extensions: false))
           assert_equal("#{@dir1}/enoent",     cache.find('./enoent'))