diff --git a/lib/tapioca/dsl/compilers/active_record_relations.rb b/lib/tapioca/dsl/compilers/active_record_relations.rb
index dd56639de..0ef175bb0 100644
--- a/lib/tapioca/dsl/compilers/active_record_relations.rb
+++ b/lib/tapioca/dsl/compilers/active_record_relations.rb
@@ -597,7 +597,7 @@ def create_relation_methods
                     sig.return_type = mod == relation_methods_module ? RelationClassName : AssociationRelationClassName
                   end
                   method.add_sig do |sig|
-                    sig.add_param("blk", "T.proc.params(record: #{constant_name}).returns(T::Boolean)")
+                    sig.add_param("blk", "T.proc.params(record: #{constant_name}).returns(T.nilable(T::Boolean))")
                     sig.return_type = "T::Array[#{constant_name}]"
                   end
                 end
diff --git a/spec/tapioca/dsl/compilers/active_record_relations_spec.rb b/spec/tapioca/dsl/compilers/active_record_relations_spec.rb
index df132c199..9a49e05db 100644
--- a/spec/tapioca/dsl/compilers/active_record_relations_spec.rb
+++ b/spec/tapioca/dsl/compilers/active_record_relations_spec.rb
@@ -433,7 +433,7 @@ def reverse_order(*args, &blk); end
                     def rewhere(*args, &blk); end
 
                     sig { params(args: T.untyped).returns(PrivateAssociationRelation) }
-                    sig { params(blk: T.proc.params(record: ::Post).returns(T::Boolean)).returns(T::Array[::Post]) }
+                    sig { params(blk: T.proc.params(record: ::Post).returns(T.nilable(T::Boolean))).returns(T::Array[::Post]) }
                     def select(*args, &blk); end
 
                     sig { params(args: T.untyped, blk: T.untyped).returns(PrivateAssociationRelation) }
@@ -594,7 +594,7 @@ def reverse_order(*args, &blk); end
                     def rewhere(*args, &blk); end
 
                     sig { params(args: T.untyped).returns(PrivateRelation) }
-                    sig { params(blk: T.proc.params(record: ::Post).returns(T::Boolean)).returns(T::Array[::Post]) }
+                    sig { params(blk: T.proc.params(record: ::Post).returns(T.nilable(T::Boolean))).returns(T::Array[::Post]) }
                     def select(*args, &blk); end
 
                     sig { params(args: T.untyped, blk: T.untyped).returns(PrivateRelation) }
@@ -1159,7 +1159,7 @@ def reverse_order(*args, &blk); end
                     def rewhere(*args, &blk); end
 
                     sig { params(args: T.untyped).returns(PrivateAssociationRelation) }
-                    sig { params(blk: T.proc.params(record: ::Post).returns(T::Boolean)).returns(T::Array[::Post]) }
+                    sig { params(blk: T.proc.params(record: ::Post).returns(T.nilable(T::Boolean))).returns(T::Array[::Post]) }
                     def select(*args, &blk); end
 
                     sig { params(args: T.untyped, blk: T.untyped).returns(PrivateAssociationRelation) }
@@ -1320,7 +1320,7 @@ def reverse_order(*args, &blk); end
                     def rewhere(*args, &blk); end
 
                     sig { params(args: T.untyped).returns(PrivateRelation) }
-                    sig { params(blk: T.proc.params(record: ::Post).returns(T::Boolean)).returns(T::Array[::Post]) }
+                    sig { params(blk: T.proc.params(record: ::Post).returns(T.nilable(T::Boolean))).returns(T::Array[::Post]) }
                     def select(*args, &blk); end
 
                     sig { params(args: T.untyped, blk: T.untyped).returns(PrivateRelation) }