diff --git a/Lib/test/test_syntax.py b/Lib/test/test_syntax.py
index 7994fe6..0a61462 100644
--- a/Lib/test/test_syntax.py
+++ b/Lib/test/test_syntax.py
@@ -371,7 +371,9 @@
      File "<doctest test.test_syntax[42]>", line 3
    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
 
@@ -399,7 +401,7 @@
    ...                      break
    Traceback (most recent call last):
      ...
-   SystemError: too many statically nested blocks
+   SyntaxError: too many statically nested blocks
 
 This tests assignment-context; there was a bug in Python 2.5 where compiling
 a complex 'if' (one with 'elif') would fail to notice an invalid suite,
diff --git a/Misc/NEWS b/Misc/NEWS
index 9ae2221..7e762e8 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -17,6 +17,9 @@
   unicode paths with embedded null character on Windows instead of silently
   truncating them.
 
+- Issue #27514: Make having too many statically nested blocks a SyntaxError
+  instead of SystemError.
+
 Library
 -------
 
diff --git a/Python/compile.c b/Python/compile.c
index ba93fb4..9c9b236 100644
--- a/Python/compile.c
+++ b/Python/compile.c
@@ -3147,7 +3147,7 @@
 {
     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;
     }