diff -r 89821243621b Lib/test/test_syntax.py
--- a/Lib/test/test_syntax.py	Thu Jul 14 07:45:24 2016 +0300
+++ b/Lib/test/test_syntax.py	Thu Jul 14 14:31:26 2016 -0700
@@ -334,7 +334,9 @@
      ...
    SyntaxError: 'break' outside loop
 
-This should probably raise a better error than a SystemError (or none at all).
+This raises a SyntaxError, it used to raise a SystemError.
+Context for this change can be found on issue #27514
+
 In 2.5 there was a missing exception and an assert was triggered in a debug
 build.  The number of blocks must be greater than CO_MAXBLOCKS.  SF #1565514
 
@@ -362,7 +364,7 @@
    ...                      break
    Traceback (most recent call last):
      ...
-   SystemError: too many statically nested blocks
+   SyntaxError: too many statically nested blocks
 
 Misuse of the nonlocal statement can lead to a few unique syntax errors.
 
diff -r 89821243621b Python/compile.c
--- a/Python/compile.c	Thu Jul 14 07:45:24 2016 +0300
+++ b/Python/compile.c	Thu Jul 14 14:31:26 2016 -0700
@@ -4249,7 +4249,7 @@
 {
     struct fblockinfo *f;
     if (c->u->u_nfblocks >= CO_MAXBLOCKS) {
-        PyErr_SetString(PyExc_SystemError,
+        PyErr_SetString(PyExc_SyntaxError,
                         "too many statically nested blocks");
         return 0;
     }