diff --git a/lib/tapioca/dsl/compilers/active_record_associations.rb b/lib/tapioca/dsl/compilers/active_record_associations.rb
index d401d4d2f..85669d97a 100644
--- a/lib/tapioca/dsl/compilers/active_record_associations.rb
+++ b/lib/tapioca/dsl/compilers/active_record_associations.rb
@@ -173,6 +173,10 @@ def populate_associations(mod)
             add_error(<<~MSG.strip)
               Cannot generate association `#{declaration(reflection)}` on `#{constant}` since the constant `#{error.class_name}` does not exist.
             MSG
+          rescue StandardError => error
+            add_error(<<~MSG.strip)
+              Cannot generate association `#{association_name}` on `#{constant}` because of `#{error}`.".
+            MSG
           end
         end
 
diff --git a/spec/tapioca/dsl/compilers/active_record_associations_spec.rb b/spec/tapioca/dsl/compilers/active_record_associations_spec.rb
index 274c5ce26..72bff238e 100644
--- a/spec/tapioca/dsl/compilers/active_record_associations_spec.rb
+++ b/spec/tapioca/dsl/compilers/active_record_associations_spec.rb
@@ -1337,6 +1337,48 @@ def reload_post; end
                   expect_dsl_compiler_errors!
                 end
 
+                it "generates RBI file for monkey patches reflections" do
+                  add_ruby_file("schema.rb", <<~RUBY)
+                    ActiveRecord::Migration.suppress_messages do
+                      ActiveRecord::Schema.define do
+                        create_table :posts do |t|
+                        end
+                      end
+                    end
+                  RUBY
+
+                  add_ruby_file("custom_reflection.rb", <<~RUBY)
+                    class CustomReflection
+                      def parent_reflection
+                      end
+                    end
+                  RUBY
+
+                  add_ruby_file("post.rb", <<~RUBY)
+                    class Post < ActiveRecord::Base
+                      ::ActiveRecord::Reflection.add_reflection(self, :monkey, CustomReflection.new)
+                    end
+                  RUBY
+
+                  expected = <<~RBI
+                    # typed: strong
+
+                    class Post
+                      include GeneratedAssociationMethods
+
+                      module GeneratedAssociationMethods; end
+                    end
+                  RBI
+
+                  assert_equal(expected, rbi_for(:Post))
+
+                  assert_equal(1, generated_errors.size)
+
+                  assert_match(Regexp.new(<<~MSG.strip), generated_errors.first)
+                    Cannot generate association `monkey` on `Post` because of `undefined method `collection?.*
+                  MSG
+                end
+
                 it "generates RBI file for broken associations" do
                   add_ruby_file("schema.rb", <<~RUBY)
                     ActiveRecord::Migration.suppress_messages do