diff --git a/src/license_expression/_pyahocorasick.py b/src/license_expression/_pyahocorasick.py
index 2a1f5bb..2ad4a2c 100644
--- a/src/license_expression/_pyahocorasick.py
+++ b/src/license_expression/_pyahocorasick.py
@@ -492,6 +492,7 @@ def filter_overlapping(tokens):
                 else:
                     logger_debug("  del curr_tok smaller overlap:", curr_tok)
                     del tokens[i]
+                    i -= 1
                     break
             j += 1
         i += 1
diff --git a/tests/test__pyahocorasick.py b/tests/test__pyahocorasick.py
index 2cc4213..00559ab 100644
--- a/tests/test__pyahocorasick.py
+++ b/tests/test__pyahocorasick.py
@@ -17,6 +17,7 @@
 
 from license_expression._pyahocorasick import Trie
 from license_expression._pyahocorasick import Token
+from license_expression._pyahocorasick import filter_overlapping
 
 
 class TestTrie(unittest.TestCase):
@@ -315,3 +316,13 @@ def test_iter_simple(self):
         ]
 
         assert expected == result
+
+
+def test_filter_overlapping_rechecks_replacement_token():
+    tokens = [Token(0, 1), Token(1, 4), Token(4, 8), Token(10, 11)]
+    assert filter_overlapping(tokens) == [Token(4, 8), Token(10, 11)]
+
+
+def test_filter_overlapping_removes_contained_token_after_replacement():
+    tokens = [Token(0, 1), Token(1, 5), Token(2, 3), Token(8, 9)]
+    assert filter_overlapping(tokens) == [Token(1, 5), Token(8, 9)]