From 8eacf5bed9786facc9bcdc21dc096b89d0c14cb0 Mon Sep 17 00:00:00 2001
From: Kartik Kenchi <netliomax25@gmail.com>
Date: Wed, 24 Jun 2026 11:29:29 +0530
Subject: [PATCH] prefix every line of a multiline comment in Item.comment and
 add_line

---
 tests/test_items.py | 27 +++++++++++++++++++++++++++
 tomlkit/items.py    | 24 +++++++++++++++++++-----
 2 files changed, 46 insertions(+), 5 deletions(-)

diff --git a/tests/test_items.py b/tests/test_items.py
index b785a5e..15891a4 100644
--- a/tests/test_items.py
+++ b/tests/test_items.py
@@ -515,6 +515,17 @@ def test_array_add_line() -> None:
     )
 
 
+def test_array_add_line_multiline_comment_is_valid_toml() -> None:
+    t = api.array()
+    t.add_line(1, 2, 3, comment="first line\nsecond line")
+    t.add_line(indent="")
+    doc = api.document()
+    doc["a"] = t
+    rendered = doc.as_string()
+    assert "\nsecond line" not in rendered
+    assert parse(rendered).as_string() == rendered
+
+
 def test_array_add_line_invalid_value() -> None:
     t = api.array()
     with pytest.raises(ValueError, match="is not allowed"):
@@ -887,6 +898,22 @@ def test_trim_comments_when_building_inline_table() -> None:
     assert table.as_string() == '{foo = "bar", baz = "foobaz"}'
 
 
+def test_comment_method_multiline_is_valid_toml() -> None:
+    doc = api.document()
+    doc["x"] = 1
+    doc["x"].comment("first line\nsecond line")
+    rendered = doc.as_string()
+    assert rendered == "x = 1 # first line\n# second line\n"
+    assert parse(rendered).as_string() == rendered
+
+
+def test_comment_method_keeps_existing_hash_prefix() -> None:
+    doc = api.document()
+    doc["x"] = 1
+    doc["x"].comment("# already a comment")
+    assert doc.as_string() == "x = 1 # already a comment\n"
+
+
 def test_append_table_to_inline_table_raises() -> None:
     table = api.table()
     table.append("a", 1)
diff --git a/tomlkit/items.py b/tomlkit/items.py
index e9fdaff..3b2516d 100644
--- a/tomlkit/items.py
+++ b/tomlkit/items.py
@@ -232,6 +232,21 @@ 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")
 
 
+def _format_comment(comment: str) -> str:
+    """Prefix every line of ``comment`` with ``#`` so a multi-line comment
+    stays valid TOML.
+
+    Only the first line was prefixed before, so the second line onward of a
+    comment with embedded newlines rendered without a ``#`` and produced
+    output that no longer re-parses. A line that already starts with ``#`` is
+    left untouched and an empty line becomes a bare ``#``.
+    """
+    return "\n".join(
+        line if line.lstrip().startswith("#") else f"# {line}" if line else "#"
+        for line in comment.split("\n")
+    )
+
+
 class StringType(Enum):
     # Single Line Basic
     SLB = '"'
@@ -500,11 +515,8 @@ def unwrap(self) -> Any:
 
     def comment(self, comment: str) -> Item:
         """Attach a comment to this item"""
-        if not comment.strip().startswith("#"):
-            comment = "# " + comment
-
         self._trivia.comment_ws = " "
-        self._trivia.comment = comment
+        self._trivia.comment = _format_comment(comment)
 
         return self
 
@@ -1550,7 +1562,9 @@ def add_line(
         if comment:
             indent = " " if items else ""
             new_values.append(
-                Comment(Trivia(indent=indent, comment=f"# {comment}", trail=""))
+                Comment(
+                    Trivia(indent=indent, comment=_format_comment(comment), trail="")
+                )
             )
         list.extend(self, data_values)
         if len(self._value) > 0: