diff --git a/organize/walker.py b/organize/walker.py
index f217be04..7afcbb7e 100644
--- a/organize/walker.py
+++ b/organize/walker.py
@@ -3,6 +3,7 @@
 from pathlib import Path
 from typing import Iterable, Iterator, List, Literal, NamedTuple, Optional, Set
 
+from natsort import os_sorted
 from pydantic import Field
 from pydantic.dataclasses import dataclass
 
@@ -57,7 +58,10 @@ def scandir(top: str, collectfiles: bool = True) -> ScandirResult:
                 result.dirs.append(entry)
             elif collectfiles:
                 result.nondirs.append(entry)
-    return result
+    return ScandirResult(
+        dirs=os_sorted(result.dirs, key=lambda x: x.name),
+        nondirs=os_sorted(result.nondirs, key=lambda x: x.name),
+    )
 
 
 class DirActions(NamedTuple):
diff --git a/poetry.lock b/poetry.lock
index 5fedfda2..3b898363 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -830,6 +830,21 @@ files = [
     {file = "mypy_extensions-1.0.0.tar.gz", hash = "sha256:75dbf8955dc00442a438fc4d0666508a9a97b6bd41aa2f0ffe9d2f2725af0782"},
 ]
 
+[[package]]
+name = "natsort"
+version = "8.4.0"
+description = "Simple yet flexible natural sorting in Python."
+optional = false
+python-versions = ">=3.7"
+files = [
+    {file = "natsort-8.4.0-py3-none-any.whl", hash = "sha256:4732914fb471f56b5cce04d7bae6f164a592c7712e1c85f9ef585e197299521c"},
+    {file = "natsort-8.4.0.tar.gz", hash = "sha256:45312c4a0e5507593da193dedd04abb1469253b601ecaf63445ad80f0a1ea581"},
+]
+
+[package.extras]
+fast = ["fastnumbers (>=2.0.0)"]
+icu = ["PyICU (>=1.0.0)"]
+
 [[package]]
 name = "packaging"
 version = "23.2"
@@ -1553,4 +1568,4 @@ docs = ["markupsafe", "mkdocs", "mkdocs-autorefs", "mkdocs-include-markdown-plug
 [metadata]
 lock-version = "2.0"
 python-versions = "^3.9"
-content-hash = "0a1ad3d51b096c4b73f270ccd43c16f6abbeb204dce72c1ac09711f471fc197a"
+content-hash = "575390204771d58aa66010132e4656b318d58861c8d0fa96ce2360ae96f5f0c1"
diff --git a/pyproject.toml b/pyproject.toml
index 22c48245..fd4aef82 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -39,6 +39,7 @@ docx2txt = "^0.8"
 ExifRead = "2.3.2"                                                        # Pinned: https://github.com/tfeldmann/organize/issues/267
 Jinja2 = "^3.1.2"
 macos-tags = { version = "^1.5.1", markers = "sys_platform == 'darwin'" }
+natsort = "^8.4.0"
 pdfminer-six = "^20231228"
 platformdirs = "^4.0.0"
 pydantic = "^2.3.0"
diff --git a/tests/core/test_filter_mode.py b/tests/core/test_filter_mode.py
index f5ceaba8..8721477d 100644
--- a/tests/core/test_filter_mode.py
+++ b/tests/core/test_filter_mode.py
@@ -31,7 +31,7 @@ def test_filter_mode(fs, testoutput, filter_mode, expected_msgs):
 @pytest.mark.parametrize(
     "filter_mode, expected_msgs",
     (
-        ("any", ["foo", "baz", "x"]),
+        ("any", ["baz", "foo", "x"]),
         ("all", ["x"]),
         ("none", []),
     ),
diff --git a/tests/core/test_location.py b/tests/core/test_location.py
index 8e46631a..8dda850a 100644
--- a/tests/core/test_location.py
+++ b/tests/core/test_location.py
@@ -49,7 +49,7 @@ def test_multiple_pathes(fs, testoutput):
               - echo: '{path.name}'
         """
     ).execute(simulate=False, output=testoutput)
-    assert testoutput.messages == ["foo.txt", "bar.txt"] * 2
+    assert testoutput.messages == ["bar.txt", "foo.txt"] * 2
 
 
 def test_multiple_pathes_single_location(fs, testoutput):
@@ -66,7 +66,7 @@ def test_multiple_pathes_single_location(fs, testoutput):
               - echo: '{path.name}'
         """
     ).execute(simulate=False, output=testoutput)
-    assert testoutput.messages == ["foo.txt", "bar.txt"] * 2
+    assert testoutput.messages == ["bar.txt", "foo.txt", "bar.txt", "foo.txt"]
 
 
 def test_multiple_dirs(fs, testoutput):
diff --git a/tests/core/test_walker.py b/tests/core/test_walker.py
index 1011b6c9..330bc90c 100644
--- a/tests/core/test_walker.py
+++ b/tests/core/test_walker.py
@@ -147,3 +147,28 @@ def test_exclude_dirs(fs):
         "test",
     )
     assert len(list(Walker(exclude_dirs=["subC"]).files("/test"))) == 4
+
+
+def test_order(fs):
+    make_files(
+        {
+            "2024": {"004": "", "001": "", "003": "", "002": ""},
+            "1989": {"D": "", "C": "", "A": "", "B": ""},
+            "2000": {"B": {"2": "", "1": ""}, "A": {"1": "", "2": ""}},
+        },
+        "test",
+    )
+    assert list(Walker().files("/test")) == [
+        Path("/test/1989/A"),
+        Path("/test/1989/B"),
+        Path("/test/1989/C"),
+        Path("/test/1989/D"),
+        Path("/test/2000/A/1"),
+        Path("/test/2000/A/2"),
+        Path("/test/2000/B/1"),
+        Path("/test/2000/B/2"),
+        Path("/test/2024/001"),
+        Path("/test/2024/002"),
+        Path("/test/2024/003"),
+        Path("/test/2024/004"),
+    ]
diff --git a/tests/filters/test_extension.py b/tests/filters/test_extension.py
index 83edd47f..0487523e 100644
--- a/tests/filters/test_extension.py
+++ b/tests/filters/test_extension.py
@@ -51,7 +51,7 @@ def test_filename_move(fs, testoutput):
         """
     Config.from_string(config).execute(simulate=False, output=testoutput)
     assert testoutput.messages == [
-        "Found JPG file: test",
         "Found JPG file: asd",
         "Found JPG file: camel",
+        "Found JPG file: test",
     ]
diff --git a/tests/filters/test_python.py b/tests/filters/test_python.py
index de80ca5e..232241c8 100644
--- a/tests/filters/test_python.py
+++ b/tests/filters/test_python.py
@@ -70,9 +70,9 @@ def test_python_dict(fs, testoutput):
         """
     Config.from_string(config).execute(simulate=False, output=testoutput)
     assert testoutput.messages == [
-        "100 foo",
         "200 bar",
         "300 baz",
+        "100 foo",
     ]
 
 
diff --git a/tests/test_api.py b/tests/test_api.py
index 3e253877..6f4f9da7 100644
--- a/tests/test_api.py
+++ b/tests/test_api.py
@@ -21,4 +21,4 @@ def test_api(fs, testoutput):
         ]
     )
     config.execute(simulate=False, output=testoutput)
-    assert testoutput.messages == ["FOOFOO", "BAR", "BAZ"]
+    assert testoutput.messages == ["BAR", "BAZ", "FOOFOO"]