diff --git a/CHANGELOG b/CHANGELOG
index 647ee5372..52ebc80ce 100644
--- a/CHANGELOG
+++ b/CHANGELOG
@@ -1,6 +1,8 @@
 Changes between 2.3.4 and 2.3.5dev
 -----------------------------------
 
+- issue 280 - disable assertion rewriting on buggy CPython 2.6.0
+
 - inject "getfixture()" helper to retrieve fixtures from doctests,
   thanks Andreas Zeidler
 
diff --git a/_pytest/assertion/__init__.py b/_pytest/assertion/__init__.py
index b7ec1924d..bd3b594fd 100644
--- a/_pytest/assertion/__init__.py
+++ b/_pytest/assertion/__init__.py
@@ -39,7 +39,10 @@ def pytest_configure(config):
         except ImportError:
             mode = "reinterp"
         else:
-            if sys.platform.startswith('java'):
+            # Both Jython and CPython 2.6.0 have AST bugs that make the
+            # assertion rewriting hook malfunction.
+            if (sys.platform.startswith('java') or
+                sys.version_info[:3] == (2, 6, 0)):
                 mode = "reinterp"
     if mode != "plain":
         _load_modules(mode)