diff --git a/CHANGELOG.md b/CHANGELOG.md
index faad379..ebc203e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -21,6 +21,7 @@
 
 ### Fixed
 
+- Fix `string()` dropping a leading newline of a multiline string on round-trip: a value beginning with a newline is now rendered with an extra leading newline (the one the parser trims after the opening delimiter) so it survives re-parsing.
 - Fix invalid serialization with a duplicated comma when removing a non-edge element from a parsed inline table. ([#486](https://github.com/python-poetry/tomlkit/pull/486))
 - Fix invalid serialization with a duplicated comma when appending or inserting into a comma-first formatted array. ([#499](https://github.com/python-poetry/tomlkit/pull/499))
 - Fix `ParseError` when a sub-table extends the last element of an array of tables after an unrelated table. ([#261](https://github.com/python-poetry/tomlkit/issues/261))
diff --git a/tests/test_api.py b/tests/test_api.py
index b49c90a..b5f31bc 100644
--- a/tests/test_api.py
+++ b/tests/test_api.py
@@ -506,7 +506,7 @@ def test_create_super_table_with_aot() -> None:
         ({}, "My String\x12", '"My String\\u0012"'),
         ({}, "My String\x7f", '"My String\\u007f"'),
         ({"escape": False}, "My String\u0001", '"My String\u0001"'),
-        ({"multiline": True}, "\nMy\nString\n", '"""\nMy\nString\n"""'),
+        ({"multiline": True}, "\nMy\nString\n", '"""\n\nMy\nString\n"""'),
         ({"multiline": True}, 'My"String', '"""My"String"""'),
         ({"multiline": True}, 'My""String', '"""My""String"""'),
         ({"multiline": True}, 'My"""String', '"""My""\\"String"""'),
@@ -537,6 +537,30 @@ def test_create_string(kwargs: dict[str, Any], example: str, expected: str) -> N
     assert value.as_string() == expected
 
 
+@pytest.mark.parametrize(
+    "kwargs, example",
+    [
+        ({"multiline": True}, "\n"),
+        ({"multiline": True}, "\nMy\nString\n"),
+        ({"multiline": True}, "\r\nMy\nString"),
+        ({"multiline": True, "literal": True}, "\nMy\nString"),
+        ({"multiline": True, "literal": True}, "\r\nMy\nString"),
+    ],
+)
+def test_create_multiline_string_with_leading_newline_round_trips(
+    kwargs: dict[str, Any], example: str
+) -> None:
+    """A multiline string whose value starts with a newline must survive a
+    round-trip. The parser trims a newline immediately following the opening
+    delimiter, so the rendered form has to account for it (otherwise the
+    leading newline is silently dropped when the output is parsed again).
+    """
+    value = tomlkit.string(example, **kwargs)
+    assert str(value) == example
+    reparsed = parse(f"k = {value.as_string()}\n")["k"]
+    assert str(reparsed) == example
+
+
 @pytest.mark.parametrize(
     "kwargs, example",
     [
diff --git a/tomlkit/items.py b/tomlkit/items.py
index e9fdaff..d559bfe 100644
--- a/tomlkit/items.py
+++ b/tomlkit/items.py
@@ -2251,6 +2251,13 @@ def from_raw(
         escaped = type_.escaped_sequences
         string_value = escape_string(value, escaped) if escape and escaped else value
 
+        if type_.is_multiline() and string_value[:1] in ("\n", "\r"):
+            # A newline immediately following the opening delimiter of a
+            # multiline string is trimmed by the parser, so a value that
+            # starts with a newline would otherwise lose it on round-trip.
+            # Emit an extra leading newline (the trimmed one) to preserve it.
+            string_value = "\n" + string_value
+
         return cls(type_, decode(value), string_value, Trivia())