diff --git a/bumpversion/autocast.py b/bumpversion/autocast.py
index 06fd0ecb..f417b1aa 100644
--- a/bumpversion/autocast.py
+++ b/bumpversion/autocast.py
@@ -43,11 +43,14 @@ def listify(s: str) -> list:
     Returns:
         List of homogenous basic types.
     """
-    if "," not in s and "\n" not in s:
+    if "\n" in s:
+        str_list = s.strip().split("\n")
+    elif "," in s:
+        str_list = s.strip().split(",")
+    else:
         raise ValueError("Not a List")
 
     # derive the type of the variable
-    str_list = s.strip().split(",") if "," in s else s.strip().split("\n")
     element_caster = str
     for caster in (boolify, int, float, noneify, element_caster):
         with contextlib.suppress(ValueError):
diff --git a/tests/fixtures/legacy_multiline_search_comma.cfg b/tests/fixtures/legacy_multiline_search_comma.cfg
new file mode 100644
index 00000000..d405c298
--- /dev/null
+++ b/tests/fixtures/legacy_multiline_search_comma.cfg
@@ -0,0 +1,8 @@
+[bumpversion]
+current_version = 1.0.0
+
+[bumpversion:file:MULTILINE_SEARCH.md]
+search = **unreleased**,
+	**v{current_version}**,
+replace = **unreleased**,
+	**v{new_version}**,
diff --git a/tests/fixtures/legacy_multiline_search_comma_expected.json b/tests/fixtures/legacy_multiline_search_comma_expected.json
new file mode 100644
index 00000000..e7fdc5f7
--- /dev/null
+++ b/tests/fixtures/legacy_multiline_search_comma_expected.json
@@ -0,0 +1,11 @@
+{
+  "current_version": "1.0.0",
+  "files": [
+    {
+      "filename": "MULTILINE_SEARCH.md",
+      "search": "**unreleased**,\n**v{current_version}**,",
+      "replace": "**unreleased**,\n**v{new_version}**,"
+    }
+  ],
+  "parts": {}
+}
diff --git a/tests/test_autocast.py b/tests/test_autocast.py
index 28204ad8..d3d92a4b 100644
--- a/tests/test_autocast.py
+++ b/tests/test_autocast.py
@@ -46,6 +46,7 @@ def test_noneify():
         param("1,2,3,4", [1, 2, 3, 4], id="int"),
         param("1\n2\n3\n4", [1, 2, 3, 4], id="int"),
         param("s,t,r", ["s", "t", "r"], id="str"),
+        param("s,\nt,\nr\n", ["s,", "t,", "r"], id="str_newline"),
         param("1.1,2,3.14", [1.1, 2.0, 3.14], id="float"),
         param("True,False,true,false", [True, False, True, False], id="bool"),
         param("None,None,None", [None, None, None], id="none"),
@@ -75,6 +76,7 @@ def test_listify_invalid():
         param("False", False, id="False"),
         param("1,2,3,4", [1, 2, 3, 4], id="int-list"),
         param("s,t,r", ["s", "t", "r"], id="str-list"),
+        param("s,\nt,\nr\n", ["s,", "t,", "r"], id="str-list-newline"),
         param("1", 1, id="int"),
         param("1.0", 1.0, id="float"),
         param(1, 1, id="real-int"),
diff --git a/tests/test_config/test_files_legacy.py b/tests/test_config/test_files_legacy.py
index a0e0b025..53a95e00 100644
--- a/tests/test_config/test_files_legacy.py
+++ b/tests/test_config/test_files_legacy.py
@@ -35,6 +35,11 @@ def cfg_file(request) -> str:
     [
         param("basic_cfg.cfg", "basic_cfg_expected.json", id="ini basic cfg"),
         param("legacy_multiline_search.cfg", "legacy_multiline_search_expected.json", id="multiline search cfg"),
+        param(
+            "legacy_multiline_search_comma.cfg",
+            "legacy_multiline_search_comma_expected.json",
+            id="multiline search comma cfg",
+        ),
     ],
 )
 def test_read_ini_file(conf_file: str, expected_file: str, fixtures_path: Path) -> None: