diff --git a/class.c b/class.c
index 12a67d16bc..68cfbfb257 100644
--- a/class.c
+++ b/class.c
@@ -351,7 +351,7 @@ copy_tables(VALUE clone, VALUE orig)
     }
 }
 
-static void ensure_origin(VALUE klass);
+static bool ensure_origin(VALUE klass);
 
 /* :nodoc: */
 VALUE
@@ -1014,27 +1014,31 @@ clear_module_cache_i(ID id, VALUE val, void *data)
     return ID_TABLE_CONTINUE;
 }
 
+static bool
+module_in_super_chain(const VALUE klass, VALUE module)
+{
+    struct rb_id_table *const klass_m_tbl = RCLASS_M_TBL(RCLASS_ORIGIN(klass));
+    if (klass_m_tbl) {
+        while (module) {
+            if (klass_m_tbl == RCLASS_M_TBL(module))
+                return true;
+            module = RCLASS_SUPER(module);
+        }
+    }
+    return false;
+}
+
 static int
-include_modules_at(const VALUE klass, VALUE c, VALUE module, int search_super)
+do_include_modules_at(const VALUE klass, VALUE c, VALUE module, int search_super, bool check_cyclic)
 {
     VALUE p, iclass, origin_stack = 0;
     int method_changed = 0, constant_changed = 0, add_subclass;
     long origin_len;
     VALUE klass_origin = RCLASS_ORIGIN(klass);
-    struct rb_id_table *const klass_m_tbl = RCLASS_M_TBL(klass_origin);
     VALUE original_klass = klass;
 
-    if (klass_m_tbl) {
-        VALUE original_module = module;
-
-        while (module) {
-            if (klass_m_tbl == RCLASS_M_TBL(module))
-                return -1;
-            module = RCLASS_SUPER(module);
-        }
-
-        module = original_module;
-    }
+    if (check_cyclic && module_in_super_chain(klass, module))
+        return -1;
 
     while (module) {
         int c_seen = FALSE;
@@ -1129,6 +1133,12 @@ include_modules_at(const VALUE klass, VALUE c, VALUE module, int search_super)
     return method_changed;
 }
 
+static int
+include_modules_at(const VALUE klass, VALUE c, VALUE module, int search_super)
+{
+    return do_include_modules_at(klass, c, module, search_super, true);
+}
+
 static enum rb_id_table_iterator_result
 move_refined_method(ID key, VALUE value, void *data)
 {
@@ -1169,7 +1179,7 @@ cache_clear_refined_method(ID key, VALUE value, void *data)
     return ID_TABLE_CONTINUE;
 }
 
-static void
+static bool
 ensure_origin(VALUE klass)
 {
     VALUE origin = RCLASS_ORIGIN(klass);
@@ -1182,20 +1192,24 @@ ensure_origin(VALUE klass)
 	RCLASS_M_TBL_INIT(klass);
         rb_id_table_foreach(RCLASS_M_TBL(origin), cache_clear_refined_method, (void *)klass);
 	rb_id_table_foreach(RCLASS_M_TBL(origin), move_refined_method, (void *)klass);
+        return true;
     }
+    return false;
 }
 
 void
 rb_prepend_module(VALUE klass, VALUE module)
 {
-    int changed = 0;
-    bool klass_had_no_origin = RCLASS_ORIGIN(klass) == klass;
+    int changed;
+    bool klass_had_no_origin;
 
     ensure_includable(klass, module);
-    ensure_origin(klass);
-    changed = include_modules_at(klass, klass, module, FALSE);
-    if (changed < 0)
-	rb_raise(rb_eArgError, "cyclic prepend detected");
+    if (module_in_super_chain(klass, module))
+        rb_raise(rb_eArgError, "cyclic prepend detected");
+
+    klass_had_no_origin = ensure_origin(klass);
+    changed = do_include_modules_at(klass, klass, module, FALSE, false);
+    RUBY_ASSERT(changed >= 0); // already checked for cyclic prepend above
     if (changed) {
 	rb_vm_check_redefinition_by_prepend(klass);
     }
diff --git a/test/ruby/test_module.rb b/test/ruby/test_module.rb
index 0a5597fd6c..e5152b1012 100644
--- a/test/ruby/test_module.rb
+++ b/test/ruby/test_module.rb
@@ -485,6 +485,19 @@ class TestModule < Test::Unit::TestCase
     assert_equal([m], m.ancestors)
   end
 
+  def test_bug17590
+    m = Module.new
+    c = Class.new
+    c.prepend(m)
+    c.include(m)
+    m.prepend(m) rescue nil
+    m2 = Module.new
+    m2.prepend(m)
+    c.include(m2)
+
+    assert_equal([m, c, m2] + Object.ancestors, c.ancestors)
+  end
+
   def test_prepend_works_with_duped_classes
     m = Module.new
     a = Class.new do