diff --git a/lib/steep/subtyping/check.rb b/lib/steep/subtyping/check.rb
index 1418a1cc9..6c78d36c7 100644
--- a/lib/steep/subtyping/check.rb
+++ b/lib/steep/subtyping/check.rb
@@ -347,7 +347,7 @@ def check_type0(relation)
 
         when relation.super_type.is_a?(AST::Types::Union)
           Any(relation) do |result|
-            relation.super_type.types.sort_by {|ty| (path = hole_path(ty)) ? -path.size : 1 }.each do |super_type|
+            relation.super_type.types.sort_by {|ty| (path = hole_path(ty)) ? -path.size : -Float::INFINITY }.each do |super_type|
               rel = Relation.new(sub_type: relation.sub_type, super_type: super_type)
               result.add(rel) do
                 check_type(rel)
@@ -357,7 +357,7 @@ def check_type0(relation)
 
         when relation.sub_type.is_a?(AST::Types::Intersection)
           Any(relation) do |result|
-            relation.sub_type.types.sort_by {|ty| (path = hole_path(ty)) ? -path.size : 1 }.each do |sub_type|
+            relation.sub_type.types.sort_by {|ty| (path = hole_path(ty)) ? -path.size : -Float::INFINITY }.each do |sub_type|
               rel = Relation.new(sub_type: sub_type, super_type: relation.super_type)
               result.add(rel) do
                 check_type(rel)
diff --git a/test/type_construction_test.rb b/test/type_construction_test.rb
index 9761eafa7..62c448dec 100644
--- a/test/type_construction_test.rb
+++ b/test/type_construction_test.rb
@@ -8577,6 +8577,53 @@ def flat_map: [A] () { (String) -> (A | Array[A]) } -> Array[A]
     end
   end
 
+  def test_filter_map
+    with_checker(<<-RBS) do |checker|
+class FilterMap
+  def filter_map: [A] () { (String) -> (A | nil | false) } -> Array[A]
+end
+    RBS
+
+      source = parse_ruby(<<-'RUBY')
+# @type var a: FilterMap
+a = _ = nil
+a.filter_map do |s|
+  if s
+    s.size
+  end
+end
+      RUBY
+
+      with_standard_construction(checker, source) do |construction, typing|
+        type, _, _ = construction.synthesize(source.node)
+
+        assert_no_error typing
+        assert_equal parse_type("::Array[::Integer]"), type
+      end
+    end
+  end
+
+  def test_filter_map_compact
+    with_checker(<<-RBS) do |checker|
+class Array[unchecked out Element]
+  def filter_map: [A] () { (Element) -> (A | nil | false) } -> Array[A]
+end
+    RBS
+
+      source = parse_ruby(<<-'RUBY')
+a = ["1", nil]
+a.filter_map(&:itself)
+      RUBY
+
+      with_standard_construction(checker, source) do |construction, typing|
+        type, _, _ = construction.synthesize(source.node)
+
+        assert_no_error typing
+        assert_equal parse_type("::Array[::String]"), type
+      end
+    end
+  end
+
   def test_to_proc_syntax_optional_arg
     with_checker(<<-RBS) do |checker|
 class OptionalArgMethod