diff --git a/sql_metadata/generalizator.py b/sql_metadata/generalizator.py
index f0639517..cdb8283a 100644
--- a/sql_metadata/generalizator.py
+++ b/sql_metadata/generalizator.py
@@ -9,6 +9,9 @@
 
 import re
 
+from sqlglot.errors import TokenError
+from sqlglot.tokens import Tokenizer, TokenType
+
 from sql_metadata.comments import strip_comments
 
 
@@ -36,12 +39,33 @@ def __init__(self, sql: str = ""):
         self._raw_query = sql
 
     # SQL queries normalization (#16)
+    @staticmethod
+    def _normalize_strings(sql: str) -> str:
+        """Replace whole string tokens, including doubled quote escapes."""
+        if "'" not in sql:
+            return sql
+        try:
+            tokens = Tokenizer().tokenize(sql)
+        except TokenError:
+            # Preserve best-effort normalization of lexically malformed SQL.
+            return re.sub(r"'[^\']*'", "X", sql)
+
+        parts: list[str] = []
+        previous_end = 0
+        for token in tokens:
+            if token.token_type in (TokenType.STRING, TokenType.NATIONAL_STRING):
+                # Keep the N/n prefix, as the previous normalization did.
+                start = token.start + (token.token_type == TokenType.NATIONAL_STRING)
+                parts.extend((sql[previous_end:start], "X"))
+                previous_end = token.end + 1
+        return "".join(parts) + sql[previous_end:]
+
     @staticmethod
     def _normalize_likes(sql: str) -> str:
         """Normalise and collapse repeated ``LIKE`` clauses.
 
-        Strips ``%`` wildcards, replaces ``LIKE '...'`` with ``LIKE X``,
-        and collapses consecutive ``or/and ... LIKE X`` clauses into a
+        Strips ``%`` wildcards and collapses consecutive
+        ``or/and ... LIKE X`` clauses into a
         single instance with ``...`` suffix.
 
         :param sql: SQL string with LIKE clauses.
@@ -51,9 +75,6 @@ def _normalize_likes(sql: str) -> str:
         """
         sql = sql.replace("%", "")
 
-        # LIKE '%bot'
-        sql = re.sub(r"LIKE '[^\']+'", "LIKE X", sql)
-
         # or all_groups LIKE X or all_groups LIKE X
         found = re.finditer(r"(or|and) [^\s]+ LIKE X", sql, flags=re.IGNORECASE)
         like_matches = [m.group(0) for m in found]
@@ -86,9 +107,9 @@ def generalize(self) -> str:
         1. Strip comments.
         2. Remove double-quotes.
         3. Collapse multiple spaces.
-        4. Normalise ``LIKE`` clauses.
-        5. Replace escaped characters.
-        6. Replace string literals with ``X``.
+        4. Replace escaped characters.
+        5. Replace string literals with ``X``.
+        6. Normalise ``LIKE`` clauses.
         7. Collapse whitespace to single spaces.
         8. Replace numbers with ``N``.
         9. Collapse ``IN (...)`` / ``VALUES (...)`` lists to ``(XYZ)``.
@@ -107,14 +128,11 @@ def generalize(self) -> str:
         # multiple spaces
         sql = re.sub(r"\s{2,}", " ", sql)
 
-        # handle LIKE statements
-        sql = self._normalize_likes(sql)
-
         sql = re.sub(r"\\\\", "", sql)
         sql = re.sub(r"\\'", "", sql)
         sql = re.sub(r'\\"', "", sql)
-        sql = re.sub(r"'[^\']*'", "X", sql)
-        sql = re.sub(r'"[^\"]*"', "X", sql)
+        sql = self._normalize_strings(sql)
+        sql = self._normalize_likes(sql)
 
         # All newlines, tabs, etc replaced by single space
         sql = re.sub(r"\s+", " ", sql)
diff --git a/test/test_generalize_escaped_strings.py b/test/test_generalize_escaped_strings.py
new file mode 100644
index 00000000..09487de0
--- /dev/null
+++ b/test/test_generalize_escaped_strings.py
@@ -0,0 +1,20 @@
+import pytest
+
+from sql_metadata import Parser
+
+
+@pytest.mark.parametrize("literal", ["'O''Reilly'", "'a''b''c'", "''''"])
+@pytest.mark.parametrize(
+    "prefix",
+    ["SELECT ", "SELECT N", "SELECT n", "SELECT name FROM authors WHERE name LIKE "],
+)
+def test_generalize_doubled_quotes_as_one_literal(literal: str, prefix: str) -> None:
+    assert Parser(prefix + literal).generalize == prefix + "X"
+
+
+def test_generalize_separate_literals() -> None:
+    assert Parser("SELECT 'O''Reilly', '', 'ordinary'").generalize == "SELECT X, X, X"
+
+
+def test_generalize_unterminated_literal_remains_best_effort() -> None:
+    assert Parser("SELECT 'unterminated").generalize == "SELECT 'unterminated"