diff --git a/src/univers/version_constraint.py b/src/univers/version_constraint.py
index 36ec6d81..2b782037 100644
--- a/src/univers/version_constraint.py
+++ b/src/univers/version_constraint.py
@@ -202,6 +202,11 @@ def split(string):
         >>> assert VersionConstraint.split("<2.3") == ("<", "2.3",)
         >>> assert VersionConstraint.split(">2.3") == (">", "2.3",)
         >>> assert VersionConstraint.split("!=2.3") == ("!=", "2.3",)
+        >>> try:
+        ...     VersionConstraint.split("<<2.3")
+        ...     raise Exception("ValueError should be raised")
+        ... except ValueError:
+        ...     pass
         """
         constraint_string = remove_spaces(string)
 
@@ -212,9 +217,15 @@ def split(string):
         for comparator in COMPARATORS:
             if constraint_string.startswith(comparator):
                 # NOTE: we do not report an error if this is not valid
-                version = constraint_string.lstrip(comparator)
+                version = constraint_string[len(comparator) :]
                 if comparator == "*":
                     version = ""
+
+                # Reject malformed repeated comparator prefixes such as
+                # "<<2.3" and ">>2.3" in VERS constraints which are explicitly not supported in VERS.
+                elif version and version[0] in "<>!=*":
+                    raise ValueError(f"Unknown comparator in constraint: {constraint_string!r}")
+                
                 return comparator, version
 
         # default to equality
diff --git a/tests/test_version_constraint.py b/tests/test_version_constraint.py
index b58828ec..34c1450e 100644
--- a/tests/test_version_constraint.py
+++ b/tests/test_version_constraint.py
@@ -87,3 +87,11 @@ def test_invert_opertaion(original, inverted):
         assert constraint.invert() == inverted_constraint
     else:
         assert constraint.invert() is None
+
+@pytest.mark.parametrize("spec", ["<<2.3", ">>2.3"])
+def test_invalid_vers_comparator_prefixes(spec):
+    with pytest.raises(ValueError, match="Unknown comparator"):
+        VersionConstraint.from_string(
+            string=spec,
+            version_class=versions.SemverVersion,
+        )
\ No newline at end of file