diff --git a/lib/tapioca/dsl/compilers/active_record_associations.rb b/lib/tapioca/dsl/compilers/active_record_associations.rb
index da54fdc4b..ce2f56259 100644
--- a/lib/tapioca/dsl/compilers/active_record_associations.rb
+++ b/lib/tapioca/dsl/compilers/active_record_associations.rb
@@ -108,6 +108,9 @@ class ActiveRecordAssociations < Compiler
         class SourceReflectionError < StandardError
         end
 
+        class SelfReferentialSourceReflectionError < StandardError
+        end
+
         class MissingConstantError < StandardError
           #: String
           attr_reader :class_name
@@ -167,6 +170,10 @@ def populate_associations(mod)
             add_error(<<~MSG.strip)
               Cannot generate association `#{reflection.name}` on `#{constant}` since the source of the through association is missing.
             MSG
+          rescue SelfReferentialSourceReflectionError
+            add_error(<<~MSG.strip)
+              Cannot generate association `#{reflection.name}` on `#{constant}` since the source of the through association is itself. Specify the `source:` option.
+            MSG
           rescue MissingConstantError => error
             add_error(<<~MSG.strip)
               Cannot generate association `#{declaration(reflection)}` on `#{constant}` since the constant `#{error.class_name}` does not exist.
@@ -279,6 +286,8 @@ def validate_reflection!(reflection)
           # and fails with a cryptic error, otherwise.
           if reflection.through_reflection?
             raise SourceReflectionError unless reflection.source_reflection
+            # A source reflection pointing back to itself makes `.klass` recurse forever
+            raise SelfReferentialSourceReflectionError if reflection.source_reflection.equal?(reflection)
           end
 
           # For non-polymorphic reflections, `.klass` should not be raising
diff --git a/spec/tapioca/dsl/compilers/active_record_associations_spec.rb b/spec/tapioca/dsl/compilers/active_record_associations_spec.rb
index 5999f9439..c8b1e286b 100644
--- a/spec/tapioca/dsl/compilers/active_record_associations_spec.rb
+++ b/spec/tapioca/dsl/compilers/active_record_associations_spec.rb
@@ -816,6 +816,22 @@ def shop_previously_changed?; end
                     Cannot generate association `manager` on `Post` since the source of the through association is missing.
                   MSG
                 end
+
+                it "generates RBI file for has_many :through association whose source is itself" do
+                  add_ruby_file("group.rb", <<~RUBY)
+                    class Group < ActiveRecord::Base
+                      has_many :sub_groups, class_name: "Group", foreign_key: "parent_id"
+                      has_many :child_group_members, through: :sub_groups
+                    end
+                  RUBY
+
+                  refute_includes(rbi_for(:Group), "child_group_members")
+
+                  assert_equal(1, generated_errors.size)
+                  assert_equal(<<~MSG.strip, generated_errors.first)
+                    Cannot generate association `child_group_members` on `Group` since the source of the through association is itself. Specify the `source:` option.
+                  MSG
+                end
               end
             end