diff --git a/README.md b/README.md
index 94f9385c..10211e58 100644
--- a/README.md
+++ b/README.md
@@ -80,8 +80,8 @@ If a file is not properly formatted, the exit code will be non-zero.
 foo@bar:~$ mdformat --help
 usage: mdformat [-h] [--check] [--no-validate] [--version] [--number]
                 [--wrap {keep,no,INTEGER}] [--end-of-line {lf,crlf,keep}]
-                [--exclude PATTERN] [--extensions EXTENSION]
-                [--codeformatters LANGUAGE]
+                [--max-nesting INTEGER] [--exclude PATTERN]
+                [--extensions EXTENSION] [--codeformatters LANGUAGE]
                 [paths ...]
 
 CommonMark compliant Markdown formatter
@@ -99,6 +99,11 @@ options:
                         paragraph word wrap mode (default: keep)
   --end-of-line {lf,crlf,keep}
                         output file line ending mode (default: lf)
+  --max-nesting INTEGER
+                        maximum allowed nesting depth of blockquotes and lists
+                        (default: 20). Content nested deeper than this is
+                        silently dropped by the parser; raise this for deeply
+                        nested documents
   --exclude PATTERN     exclude files that match the Unix-style glob pattern
                         (multiple allowed)
   --extensions EXTENSION
diff --git a/docs/users/configuration_file.md b/docs/users/configuration_file.md
index 508f19e9..8ada81bc 100644
--- a/docs/users/configuration_file.md
+++ b/docs/users/configuration_file.md
@@ -21,6 +21,7 @@ wrap = "keep"         # options: {"keep", "no", INTEGER}
 number = false        # options: {false, true}
 end_of_line = "lf"    # options: {"lf", "crlf", "keep"}
 validate = true       # options: {false, true}
+max_nesting = 20      # options: a positive integer
 # extensions = [      # options: a list of enabled extensions (default: all installed are enabled)
 #     "gfm",
 #     "toc",
diff --git a/src/mdformat/_cli.py b/src/mdformat/_cli.py
index 682b7896..30329aa1 100644
--- a/src/mdformat/_cli.py
+++ b/src/mdformat/_cli.py
@@ -13,7 +13,7 @@
 
 import mdformat
 from mdformat._conf import DEFAULT_OPTS, InvalidConfError, read_toml_opts
-from mdformat._util import detect_newline_type, is_md_equal
+from mdformat._util import detect_newline_type, is_md_equal, required_nesting_depth
 import mdformat.plugins
 
 
@@ -23,6 +23,39 @@ def emit(self, record: logging.LogRecord) -> None:
             sys.stderr.write(f"Warning: {record.msg}\n")
 
 
+def _print_max_nesting_error(
+    path_str: str,
+    original_str: str,
+    *,
+    opts: Mapping,
+    extensions: Mapping,
+    codeformatters: Mapping,
+) -> bool:
+    """Print error and return `True` if `max_nesting` caused the mismatch."""
+    configured_max_nesting = opts["max_nesting"]
+    needed_depth = required_nesting_depth(
+        original_str,
+        options=opts,
+        extensions=extensions,
+        codeformatters=codeformatters,
+    )
+    if needed_depth is None or needed_depth <= configured_max_nesting:
+        return False
+    print_error(
+        f'Could not format "{path_str}".',
+        paragraphs=[
+            f"This document nests blockquotes and/or lists {needed_depth} "
+            "levels deep, but 'max_nesting' is set to "
+            f"{configured_max_nesting}. Content nested beyond that "
+            "limit is silently dropped by the parser, "
+            "which is why formatting changed the document's meaning. "
+            f"Raise the limit, e.g. `--max-nesting={needed_depth}` "
+            "or `max_nesting` in `.mdformat.toml`.",
+        ],
+    )
+    return True
+
+
 def run(cli_args: Sequence[str], cache_toml: bool = True) -> int:  # noqa: C901
     arg_parser = make_arg_parser(
         mdformat.plugins._PARSER_EXTENSION_DISTS,
@@ -162,6 +195,14 @@ def run(cli_args: Sequence[str], cache_toml: bool = True) -> int:  # noqa: C901
                     codeformatters=enabled_codeformatters,
                 )
             ):
+                if _print_max_nesting_error(
+                    path_str,
+                    original_str,
+                    opts=opts,
+                    extensions=enabled_parserplugins,
+                    codeformatters=enabled_codeformatters,
+                ):
+                    return 1
                 print_error(
                     f'Could not format "{path_str}".',
                     paragraphs=[
@@ -195,6 +236,13 @@ def validate_wrap_arg(value: str) -> str | int:
     return width
 
 
+def validate_max_nesting_arg(value: str) -> int:
+    max_nesting = int(value)
+    if max_nesting < 1:
+        raise ValueError("max-nesting must be a positive integer")
+    return max_nesting
+
+
 def make_arg_parser(
     parser_extension_dists: Mapping[str, tuple[str, list[str]]],
     codeformatter_dists: Mapping[str, tuple[str, list[str]]],
@@ -241,6 +289,14 @@ def make_arg_parser(
         choices=("lf", "crlf", "keep"),
         help="output file line ending mode (default: lf)",
     )
+    parser.add_argument(
+        "--max-nesting",
+        type=validate_max_nesting_arg,
+        metavar="INTEGER",
+        help="maximum allowed nesting depth of blockquotes and lists "
+        "(default: 20). Content nested deeper than this is silently "
+        "dropped by the parser; raise this for deeply nested documents",
+    )
     if sys.version_info >= (3, 13):  # pragma: >=3.13 cover
         parser.add_argument(
             "--exclude",
@@ -327,6 +383,7 @@ class InvalidPath(Exception):
     """Exception raised when a path does not exist."""
 
     def __init__(self, path: Path):
+        super().__init__(path)
         self.path = path
 
 
diff --git a/src/mdformat/_conf.py b/src/mdformat/_conf.py
index d50a798d..d29216f7 100644
--- a/src/mdformat/_conf.py
+++ b/src/mdformat/_conf.py
@@ -6,7 +6,7 @@
 from types import MappingProxyType
 
 from mdformat._compat import tomllib
-from mdformat._util import EMPTY_MAP
+from mdformat._util import DEFAULT_MAX_NESTING, EMPTY_MAP
 
 DEFAULT_OPTS = MappingProxyType(
     {
@@ -18,6 +18,7 @@
         "plugin": EMPTY_MAP,
         "extensions": None,
         "codeformatters": None,
+        "max_nesting": DEFAULT_MAX_NESTING,
     }
 )
 
@@ -94,6 +95,14 @@ def _validate_values(opts: Mapping, conf_path: Path) -> None:  # noqa: C901
         for lang in opts["codeformatters"]:
             if not isinstance(lang, str):
                 raise InvalidConfError(f"Invalid 'codeformatters' value in {conf_path}")
+    if "max_nesting" in opts:
+        max_nesting_value = opts["max_nesting"]
+        if not (
+            isinstance(max_nesting_value, int)
+            and not isinstance(max_nesting_value, bool)
+            and max_nesting_value > 0
+        ):
+            raise InvalidConfError(f"Invalid 'max_nesting' value in {conf_path}")
 
 
 def _validate_keys(opts: Mapping, conf_path: Path) -> None:
diff --git a/src/mdformat/_util.py b/src/mdformat/_util.py
index 23472528..15166334 100644
--- a/src/mdformat/_util.py
+++ b/src/mdformat/_util.py
@@ -13,6 +13,7 @@
 
 NULL_CTX = nullcontext()
 EMPTY_MAP: MappingProxyType = MappingProxyType({})
+DEFAULT_MAX_NESTING = 20
 
 RE_NEWLINES = re.compile(r"\r\n|\r|\n")
 RE_HTML_START_SPACE_PREFIX = re.compile(r" (<[a-zA-Z][-a-zA-Z0-9]*>)")
@@ -31,6 +32,7 @@ def build_mdit(
 
     mdit = MarkdownIt(renderer_cls=renderer_cls)
     mdit.options["mdformat"] = mdformat_opts
+    mdit.options["maxNesting"] = mdformat_opts.get("max_nesting", DEFAULT_MAX_NESTING)
     # store reference labels in link/image tokens
     mdit.options["store_labels"] = True
 
@@ -117,6 +119,32 @@ def is_md_equal(
     return html_texts["md1"] == html_texts["md2"]
 
 
+def required_nesting_depth(
+    md: str,
+    *,
+    options: Mapping[str, Any] = EMPTY_MAP,
+    extensions: Iterable[str] = (),
+    codeformatters: Iterable[str] = (),
+) -> int | None:
+    """Return how many levels of blockquote/list nesting is required."""
+    # Lazy import to improve module import time
+    from markdown_it.renderer import RendererHTML
+
+    nesting_probe_ceiling = 500  # Below default Python recursion limit
+    probe_opts = {**options, "max_nesting": nesting_probe_ceiling}
+    try:
+        mdit = build_mdit(
+            RendererHTML,
+            mdformat_opts=probe_opts,
+            extensions=extensions,
+            codeformatters=codeformatters,
+        )
+        tokens = mdit.parse(md)
+    except RecursionError:
+        return None
+    return max((token.level for token in tokens), default=-1) + 1
+
+
 def detect_newline_type(md: str, eol_setting: str) -> Literal["\n", "\r\n"]:
     """Returns the newline-character to be used for output.
 
diff --git a/tests/test_api.py b/tests/test_api.py
index 73177d7a..820dd947 100644
--- a/tests/test_api.py
+++ b/tests/test_api.py
@@ -6,6 +6,7 @@
 import mdformat
 from mdformat._util import is_md_equal
 from mdformat.renderer import MDRenderer
+from tests.utils import nested_list_markdown
 
 UNFORMATTED_MARKDOWN = "\n\n# A header\n\n"
 FORMATTED_MARKDOWN = "# A header\n"
@@ -90,6 +91,16 @@ def test_api_options():
     assert mdformat.text(non_numbered, options={"number": True}) == numbered
 
 
+def test_max_nesting__deeply_nested_list():
+    text = nested_list_markdown(100)
+    assert mdformat.text(text, options={"max_nesting": 500}) == text
+
+
+def test_max_nesting__default_truncates_deeply_nested_list():
+    text = nested_list_markdown(100)
+    assert mdformat.text(text) != text
+
+
 def test_eol__lf(tmp_path):
     file_path = tmp_path / "test.md"
     file_path.write_bytes(b"Oi\r\n")
diff --git a/tests/test_cli.py b/tests/test_cli.py
index 28c36223..62c6b7a2 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -12,6 +12,7 @@
     UNFORMATTED_MARKDOWN,
     ASTChangingPlugin,
     PrefixPostprocessPlugin,
+    nested_list_markdown,
 )
 
 
@@ -269,6 +270,38 @@ def test_bad_wrap_width(capsys):
     assert "error: argument --wrap" in captured.err
 
 
+def test_max_nesting(tmp_path):
+    file_path = tmp_path / "test.md"
+    text = nested_list_markdown(100)
+    file_path.write_text(text)
+
+    assert run([str(file_path), "--max-nesting=500"]) == 0
+    assert file_path.read_text() == text
+
+
+def test_max_nesting__too_low(tmp_path, capsys):
+    file_path = tmp_path / "test.md"
+    text = nested_list_markdown(100)
+    file_path.write_text(text)
+
+    assert run([str(file_path)]) == 1
+    assert file_path.read_text() == text
+    captured = capsys.readouterr()
+    err = " ".join(captured.err.split())
+    assert "nests blockquotes and/or lists" in err
+    assert "'max_nesting' is set to 20" in err
+    assert "--max-nesting=" in err
+
+
+def test_bad_max_nesting(capsys):
+    with pytest.raises(SystemExit) as exc_info:
+        run(["some-path.md", "--max-nesting=0"])
+
+    assert exc_info.value.code == 2
+    captured = capsys.readouterr()
+    assert "error: argument --max-nesting" in captured.err
+
+
 def test_eol__lf(tmp_path):
     file_path = tmp_path / "test.md"
     file_path.write_bytes(b"Oi\r\n")
@@ -362,15 +395,12 @@ def test_get_plugin_info_str():
         {"mdformat-tables": ("0.1.0", ["tables"])},
         {"mdformat-black": ("12.1.0", ["python"])},
     )
-    assert (
-        info
-        == """\
+    assert info == """\
 installed codeformatters:
   mdformat-black: python
 
 installed extensions:
   mdformat-tables: tables"""
-    )
 
 
 def test_no_timestamp_modify(tmp_path):
diff --git a/tests/test_config_file.py b/tests/test_config_file.py
index ec16eea8..895b6e53 100644
--- a/tests/test_config_file.py
+++ b/tests/test_config_file.py
@@ -4,7 +4,19 @@
 import pytest
 
 from mdformat._cli import run
-from tests.utils import FORMATTED_MARKDOWN, UNFORMATTED_MARKDOWN
+from tests.utils import FORMATTED_MARKDOWN, UNFORMATTED_MARKDOWN, nested_list_markdown
+
+
+def test_max_nesting_conf(tmp_path):
+    config_path = tmp_path / ".mdformat.toml"
+    config_path.write_text("max_nesting = 500")
+
+    file_path = tmp_path / "test_markdown.md"
+    text = nested_list_markdown(100)
+    file_path.write_text(text)
+
+    assert run((str(file_path),)) == 0
+    assert file_path.read_text() == text
 
 
 def test_cli_override(tmp_path):
@@ -73,6 +85,8 @@ def test_invalid_toml(tmp_path, capsys):
         ("extensions", "extensions = 'gfm'"),
         ("codeformatters", "codeformatters = ['python', 1]"),
         ("extensions", "extensions = ['gfm', 1]"),
+        ("max_nesting", "max_nesting = 0"),
+        ("max_nesting", "max_nesting = 'deep'"),
     ],
 )
 def test_invalid_conf_value(bad_conf, conf_key, tmp_path, capsys):
diff --git a/tests/test_util.py b/tests/test_util.py
index 62c8dcdb..f15c8d36 100644
--- a/tests/test_util.py
+++ b/tests/test_util.py
@@ -1,4 +1,7 @@
-from mdformat._util import is_md_equal
+import sys
+
+from mdformat._util import DEFAULT_MAX_NESTING, is_md_equal, required_nesting_depth
+from tests.utils import nested_list_markdown
 
 
 def test_is_md_equal():
@@ -48,3 +51,31 @@ def test_is_md_equal__not():
 """
     assert not is_md_equal(md1, md2)
     assert not is_md_equal(md1, md2, codeformatters=("js",))
+
+
+def test_required_nesting_depth__scales_with_actual_nesting():
+    shallow_depth = required_nesting_depth(nested_list_markdown(1))
+    deep_depth = required_nesting_depth(nested_list_markdown(30))
+
+    assert shallow_depth is not None
+    assert deep_depth is not None
+    assert shallow_depth < deep_depth
+
+
+def test_required_nesting_depth__exceeds_default_max_nesting_for_deep_lists():
+    text = nested_list_markdown(30)
+
+    depth = required_nesting_depth(text)
+
+    assert depth is not None
+    assert depth > DEFAULT_MAX_NESTING
+
+
+def test_required_nesting_depth__recursion_limit_exceeded():
+    original_limit = sys.getrecursionlimit()
+    sys.setrecursionlimit(50)
+
+    try:
+        assert required_nesting_depth(nested_list_markdown(50)) is None
+    finally:
+        sys.setrecursionlimit(original_limit)
diff --git a/tests/utils.py b/tests/utils.py
index 209c4bc2..99539bad 100644
--- a/tests/utils.py
+++ b/tests/utils.py
@@ -12,6 +12,11 @@
 FORMATTED_MARKDOWN = "# A header\n"
 
 
+def nested_list_markdown(depth: int) -> str:
+    """A bulleted list nested `depth` levels deep."""
+    return "".join(f"{'  ' * i}- item{i}\n" for i in range(depth))
+
+
 class JSONFormatterPlugin:
     """A code formatter plugin that formats JSON."""