diff --git a/Lib/test/test_re.py b/Lib/test/test_re.py
index 8e7611344b9150..5d5538c373fec8 100644
--- a/Lib/test/test_re.py
+++ b/Lib/test/test_re.py
@@ -3263,6 +3263,14 @@ def test_sre_template_invalid_group_index(self):
             _sre.template("", ["", (), ""])
         self.assertIn("an integer is required", str(cm.exception))
 
+    @cpython_only
+    def test_sre_IN_invalid_skip(self):
+        # gh-160814: the validator must reject the IN opcode with skip < 2.
+        import _sre
+        for skip in (0, 1):
+            with self.assertRaises(RuntimeError):
+                _sre.compile("x", 0, [13, skip, 1], 0, {}, ())
+
 
 class ExternalTests(unittest.TestCase):
 
diff --git a/Misc/NEWS.d/next/Library/2026-10-28-13-49-42.gh-issue-160814.DwqVVi.rst b/Misc/NEWS.d/next/Library/2026-10-28-13-49-42.gh-issue-160814.DwqVVi.rst
new file mode 100644
index 00000000000000..df50ecd73c0931
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2026-10-28-13-49-42.gh-issue-160814.DwqVVi.rst
@@ -0,0 +1,2 @@
+Fix crash in :meth:`!_sre.compile` with an ``IN`` opcode whose ``skip`` value
+is smaller than 2.
diff --git a/Modules/_sre/sre.c b/Modules/_sre/sre.c
index 47c2c4abc3ef24..1c810a419b7a29 100644
--- a/Modules/_sre/sre.c
+++ b/Modules/_sre/sre.c
@@ -2212,6 +2212,8 @@ _validate_inner(SRE_CODE *code, SRE_CODE *end, Py_ssize_t groups)
         case SRE_OP_IN_UNI_IGNORE:
         case SRE_OP_IN_LOC_IGNORE:
             GET_SKIP;
+            if (skip < 2)
+                FAIL;
             /* Stop 1 before the end; we check the FAILURE below */
             if (_validate_charset(code, code+skip-2))
                 FAIL;