diff --git a/tests/test_api.py b/tests/test_api.py
index b49c90a..9defd60 100644
--- a/tests/test_api.py
+++ b/tests/test_api.py
@@ -511,6 +511,10 @@ def test_create_super_table_with_aot() -> None:
         ({"multiline": True}, 'My""String', '"""My""String"""'),
         ({"multiline": True}, 'My"""String', '"""My""\\"String"""'),
         ({"multiline": True}, 'My""""String', '"""My""\\""String"""'),
+        # a lone CR is a control char and is escaped, but a CRLF line ending is
+        # left intact
+        ({"multiline": True}, "My\rString", '"""My\\rString"""'),
+        ({"multiline": True}, "My\r\nString", '"""My\r\nString"""'),
         (
             {"multiline": True},
             '"""My"""Str"""ing"""',
@@ -548,6 +552,9 @@ def test_create_string(kwargs: dict[str, Any], example: str, expected: str) -> N
         ({"literal": True}, "My\x0cString"),
         ({"literal": True}, "My\x7fString"),
         ({"multiline": True, "literal": True}, "My'''String"),
+        # a lone CR cannot be represented in a multiline literal string
+        ({"multiline": True, "literal": True}, "My\rString"),
+        ({"multiline": True, "literal": True}, "My\r\nMy\rString"),
     ],
 )
 def test_create_string_with_invalid_characters(
diff --git a/tomlkit/items.py b/tomlkit/items.py
index 6cbb29a..8b4d6c6 100644
--- a/tomlkit/items.py
+++ b/tomlkit/items.py
@@ -232,6 +232,12 @@ def item(value: Any, _parent: Item | None = None, _sort_keys: bool = False) -> I
     raise ConvertError(f"Unable to convert an object of {type(value)} to a TOML item")
 
 
+# A carriage return that is not the CR of a CRLF line ending. Inside a multiline
+# string only a raw line feed or a CRLF pair is a valid line ending; a lone CR is
+# a control character. Literal strings cannot escape it, basic strings must.
+_BARE_CR = re.compile(r"\r(?!\n)")
+
+
 class StringType(Enum):
     # Single Line Basic
     SLB = '"'
@@ -2239,9 +2245,15 @@ def from_raw(
         if any(c in value for c in invalid):
             raise InvalidStringError(value, invalid, type_.value)
 
+        if type_ is StringType.MLL and _BARE_CR.search(value):
+            raise InvalidStringError(value, {"\r"}, type_.value)
+
         escaped = type_.escaped_sequences
         string_value = escape_string(value, escaped) if escape and escaped else value
 
+        if type_ is StringType.MLB and escape:
+            string_value = _BARE_CR.sub(r"\\r", string_value)
+
         return cls(type_, decode(value), string_value, Trivia())