diff --git a/src/docstub-stubs/_report.pyi b/src/docstub-stubs/_report.pyi
index 1515c66..0ba8bf6 100644
--- a/src/docstub-stubs/_report.pyi
+++ b/src/docstub-stubs/_report.pyi
@@ -9,6 +9,7 @@ from typing import Any, ClassVar, Literal, Self, TextIO
 import click
 
 from ._cli_help import should_strip_ansi
+from ._utils import naive_natsort_key
 
 logger: logging.Logger
 
diff --git a/src/docstub-stubs/_utils.pyi b/src/docstub-stubs/_utils.pyi
index c29d6a8..2a42f3c 100644
--- a/src/docstub-stubs/_utils.pyi
+++ b/src/docstub-stubs/_utils.pyi
@@ -5,6 +5,7 @@ import re
 from collections.abc import Callable, Hashable, Mapping, Sequence
 from functools import lru_cache, wraps
 from pathlib import Path
+from typing import Any
 from zlib import crc32
 
 def accumulate_qualname(qualname: str, *, start_right: bool = ...) -> None: ...
@@ -18,3 +19,7 @@ def update_with_add_values(
 
 class DocstubError(Exception):
     pass
+
+_regex_digit: re.Pattern
+
+def naive_natsort_key(item: Any) -> tuple[str | int, ...]: ...
diff --git a/src/docstub/_report.py b/src/docstub/_report.py
index 86957c2..51f2514 100644
--- a/src/docstub/_report.py
+++ b/src/docstub/_report.py
@@ -8,6 +8,7 @@
 import click
 
 from ._cli_help import should_strip_ansi
+from ._utils import naive_natsort_key
 
 logger: logging.Logger = logging.getLogger(__name__)
 
@@ -297,7 +298,7 @@ def format(self, record):
             msg = f"{msg}\n{indented}"
 
         # Append locations
-        for location in sorted(src_locations):
+        for location in sorted(src_locations, key=naive_natsort_key):
             location_styled = click.style(location, fg="magenta")
             msg = f"{msg}\n    {location_styled}"
 
diff --git a/src/docstub/_utils.py b/src/docstub/_utils.py
index 297d881..e41f4f5 100644
--- a/src/docstub/_utils.py
+++ b/src/docstub/_utils.py
@@ -198,3 +198,41 @@ def update_with_add_values(*mappings, out=None):
 
 class DocstubError(Exception):
     """An error raised by docstub."""
+
+
+_regex_digit: re.Pattern = re.compile(r"(\d+)")
+
+
+def naive_natsort_key(item):
+    """Transforms strings into tuples that can be sorted in natural order [1]_.
+
+    This can be passed to the "key" argument of Python's `sorted` function.
+    This is a simple implementation that will likely miss many edge cases.
+
+    Parameters
+    ----------
+    item : Any
+        Item to generate the key from. `str` is called on this item before
+        generating the key.
+
+    Returns
+    -------
+    key : tuple[str | int, ...]
+        Key to sort by.
+
+    Examples
+    --------
+    >>> naive_natsort_key("exposure.py:0:10")
+    ('exposure.py:', 0, ':', 10, '')
+    >>> paths = ["exposure.py:180", "exposure.py:47"]
+    >>> sorted(paths, key=naive_natsort_key)
+    ['exposure.py:47', 'exposure.py:180']
+
+    References
+    ----------
+    .. [1] https://en.wikipedia.org/wiki/Natural_sort_order
+    """
+    parts = _regex_digit.split(str(item))
+    # IDEA: Every second element should always be a digit, use that?
+    key = tuple(int(part) if part.isdigit() else part for part in parts)
+    return key
diff --git a/tests/test_report.py b/tests/test_report.py
index 818421a..e25e17b 100644
--- a/tests/test_report.py
+++ b/tests/test_report.py
@@ -102,7 +102,7 @@ def test_format(self, log_record):
 
     def test_format_multiple_locations(self, log_record):
         log_record.details = "Some details"
-        log_record.src_location = ["foo.py:42", "bar.py", "a/path.py:100"]
+        log_record.src_location = ["foo.py:42", "foo.py:9", "bar.py", "a/path.py:100"]
         log_record.log_id = "E321"
 
         handler = ReportHandler()
@@ -110,10 +110,11 @@ def test_format_multiple_locations(self, log_record):
 
         expected = dedent(
             """
-            E321 The actual log message (3x)
+            E321 The actual log message (4x)
                 Some details
                 a/path.py:100
                 bar.py
+                foo.py:9
                 foo.py:42
             """
         ).strip()