diff --git a/bin/cqlsh b/bin/cqlsh
index bb91f32d26..882e06c214 100755
--- a/bin/cqlsh
+++ b/bin/cqlsh
@@ -883,6 +883,18 @@ class Shell(cmd.Cmd):
                 if trynum > self.num_retries:
                     return False
                 time.sleep(1*trynum)
+            except cql.ProgrammingError, err:
+                self.printerr(str(err))
+                # try reparsing as cql3; if successful, suggest -3
+                if self.cqlver_atleast(3):
+                    if self.parseable_as_cql2(statement):
+                        self.printerr("Perhaps you meant to use CQL 2? Try using"
+                                      " the -2 option when starting cqlsh.")
+                else:
+                    if self.parseable_as_cql3(statement):
+                        self.printerr("Perhaps you meant to use CQL 3? Try using"
+                                      " the -3 option when starting cqlsh.")
+                return False
             except CQL_ERRORS, err:
                 self.printerr(str(err))
                 return False
@@ -897,6 +909,17 @@ class Shell(cmd.Cmd):
             self.print_result(self.cursor)
         return True
 
+    # these next two functions are not guaranteed perfect; just checks if the
+    # statement parses fully according to cqlsh's own understanding of the
+    # grammar. Changes to the language in Cassandra frequently don't get
+    # updated in cqlsh right away.
+
+    def parseable_as_cql3(self, statement):
+        return cql3handling.CqlRuleSet.lex_and_whole_match(statement) is not None
+
+    def parseable_as_cql2(self, statement):
+        return cqlhandling.CqlRuleSet.lex_and_whole_match(statement) is not None
+
     def determine_decoder_for(self, cfname, ksname=None):
         decoder = ErrorHandlingSchemaDecoder
         if ksname is None:
diff --git a/pylib/cqlshlib/pylexotron.py b/pylib/cqlshlib/pylexotron.py
index 0534c87042..e66d2a0cb6 100644
--- a/pylib/cqlshlib/pylexotron.py
+++ b/pylib/cqlshlib/pylexotron.py
@@ -446,6 +446,10 @@ class ParsingRuleSet:
     def lex_and_parse(self, text, startsymbol='Start'):
         return self.parse(startsymbol, self.lex(text), init_bindings={'*SRC*': text})
 
+    def lex_and_whole_match(self, text, startsymbol='Start'):
+        tokens = self.lex(text)
+        return self.whole_match(startsymbol, tokens, srcstr=text)
+
     def complete(self, startsymbol, tokens, init_bindings=None):
         if init_bindings is None:
             init_bindings = {}