diff --git a/isort/wrap_modes.py b/isort/wrap_modes.py
index ea69dff0..961a5f72 100644
--- a/isort/wrap_modes.py
+++ b/isort/wrap_modes.py
@@ -110,6 +110,16 @@ def _hanging_indent_end_line(line: str) -> str:
     return line + "\\"
 
 
+def _add_syntax(statement: str, suffix: str, line_separator: str) -> str:
+    # Appended after a trailing comment, punctuation is commented out instead of emitted.
+    head, separator, last_line = statement.rpartition(line_separator)
+    code, comment_start, comment = last_line.partition("#")
+    if not comment_start:
+        return statement + suffix
+    spacing = code[len(code.rstrip()) :] or "  "
+    return f"{head}{separator}{code.rstrip()}{suffix}{spacing}{comment_start}{comment}"
+
+
 @_wrap_mode
 def hanging_indent(**interface: Any) -> str:
     if not interface["imports"]:
@@ -347,17 +357,25 @@ def hanging_indent_with_parentheses(**interface: Any) -> str:
         current_line = next_statement.split(interface["line_separator"])[-1]
         if len(current_line) > line_length_limit:
             next_statement = (
-                isort.comments.add_to_line(
-                    interface["comments"],
-                    interface["statement"] + ",",
-                    removed=interface["remove_comments"],
-                    comment_prefix=interface["comment_prefix"],
+                _add_syntax(
+                    isort.comments.add_to_line(
+                        interface["comments"],
+                        interface["statement"],
+                        removed=interface["remove_comments"],
+                        comment_prefix=interface["comment_prefix"],
+                    ),
+                    ",",
+                    interface["line_separator"],
                 )
                 + f"{interface['line_separator']}{interface['indent']}{next_import}"
             )
             interface["comments"] = []
         interface["statement"] = next_statement
-    return f"{interface['statement']}{',' if interface['include_trailing_comma'] else ''})"
+    if interface["include_trailing_comma"]:
+        interface["statement"] = _add_syntax(
+            interface["statement"], ",", interface["line_separator"]
+        )
+    return _add_syntax(interface["statement"], ")", interface["line_separator"])
 
 
 @_wrap_mode
diff --git a/tests/unit/test_regressions.py b/tests/unit/test_regressions.py
index 4e9b619d..7f3b4c83 100644
--- a/tests/unit/test_regressions.py
+++ b/tests/unit/test_regressions.py
@@ -1,5 +1,6 @@
 """A growing set of tests designed to ensure isort doesn't have regressions in new versions"""
 
+import ast
 from io import BytesIO, StringIO, TextIOWrapper
 
 import pytest
@@ -8,6 +9,7 @@
 import isort.sections
 from isort.core import STRING_PREFIXES
 from isort.main import main
+from isort.wrap_modes import WrapModes
 
 
 def test_isort_duplicating_comments_issue_1264():
@@ -2489,3 +2491,49 @@ def test_add_import_keeps_a_prefixed_module_docstring_first_issue_1893():
                 docstring = f"{cased}{quote}module docstring\n{quote}\n"
                 source = docstring + "import a\n"
                 assert isort.code(source, add_imports=["import a"]) == source, cased + quote
+
+
+def test_hanging_indent_with_parentheses_keeps_syntax_out_of_trailing_comments():
+    """``multi_line_output=10`` must not append a comma or the closing parenthesis after a
+    trailing comment, which silently rewrote valid code into code that no longer parses.
+
+    The mode keeps the comment on the import line (its siblings hoist it to the ``(`` line),
+    then appended punctuation to that line unconditionally.  The closing ``)`` landed inside
+    the comment, and a wrapping comma was consumed by the comment re-splice in
+    ``comments.add_to_line`` -- so the output lost a separator it never got back.
+    """
+    # Closing parenthesis captured by the comment: "'(' was never closed".
+    captured_paren = isort.code(
+        "from a import b, c  # trailing\nfrom a import d\n",
+        multi_line_output=10,
+        line_length=40,
+        force_grid_wrap=2,
+    )
+    assert ast.parse(captured_paren)
+    assert captured_paren == "from a import (b, c, d)  # trailing\n"
+
+    # Comma eaten at a wrap point: the names either side of it merged into "eta gamma".
+    lost_comma = isort.code(
+        "from mypkg.submodule import alpha, beta, gamma, delta, epsilon, zeta, eta  # noqa: F401\n",
+        multi_line_output=10,
+        line_length=79,
+    )
+    assert ast.parse(lost_comma)
+    assert "eta," in lost_comma
+
+    # No wrap mode may turn parsing code into non-parsing code.
+    for mode in WrapModes:
+        for line_length in (40, 79, 88):
+            for source in (
+                "from a import b, c  # trailing\nfrom a import d\n",
+                "from mypkg.submodule import alpha, beta, gamma, delta, epsilon, zeta  # noqa: F401\n",
+                "from mypkg.sub import alpha, beta, gamma, delta, epsilon  # type: ignore\n",
+            ):
+                for trailing_comma in (False, True):
+                    output = isort.code(
+                        source,
+                        multi_line_output=mode.value,
+                        line_length=line_length,
+                        include_trailing_comma=trailing_comma,
+                    )
+                    ast.parse(output)  # must never raise