diff --git a/pyproject.toml b/pyproject.toml
index f3f39d40c..385458aeb 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -204,15 +204,9 @@ lint.per-file-ignores."docker/wait-for-redis.py" = [
   "INP001",
   "T201",
 ]
-lint.per-file-ignores."src/documents/file_handling.py" = [
-  "PTH",
-] # TODO Enable & remove
 lint.per-file-ignores."src/documents/management/commands/document_consumer.py" = [
   "PTH",
 ] # TODO Enable & remove
-lint.per-file-ignores."src/documents/management/commands/document_exporter.py" = [
-  "PTH",
-] # TODO Enable & remove
 lint.per-file-ignores."src/documents/migrations/1012_fix_archive_files.py" = [
   "PTH",
 ] # TODO Enable & remove
@@ -222,9 +216,6 @@ lint.per-file-ignores."src/documents/models.py" = [
 lint.per-file-ignores."src/documents/parsers.py" = [
   "PTH",
 ] # TODO Enable & remove
-lint.per-file-ignores."src/documents/signals/handlers.py" = [
-  "PTH",
-] # TODO Enable & remove
 lint.per-file-ignores."src/paperless_tesseract/tests/test_parser.py" = [
   "RUF001",
 ]
diff --git a/src/documents/file_handling.py b/src/documents/file_handling.py
index 3d1a643df..3a0ffd9fb 100644
--- a/src/documents/file_handling.py
+++ b/src/documents/file_handling.py
@@ -1,4 +1,5 @@
 import os
+from pathlib import Path
 
 from django.conf import settings
 
@@ -7,19 +8,15 @@ from documents.templating.filepath import validate_filepath_template_and_render
 from documents.templating.utils import convert_format_str_to_template_format
 
 
-def create_source_path_directory(source_path):
-    os.makedirs(os.path.dirname(source_path), exist_ok=True)
+def create_source_path_directory(source_path: Path) -> None:
+    source_path.parent.mkdir(parents=True, exist_ok=True)
 
 
-def delete_empty_directories(directory, root):
-    if not os.path.isdir(directory):
+def delete_empty_directories(directory: Path, root: Path) -> None:
+    if not directory.is_dir():
         return
 
-    # Go up in the directory hierarchy and try to delete all directories
-    directory = os.path.normpath(directory)
-    root = os.path.normpath(root)
-
-    if not directory.startswith(root + os.path.sep):
+    if not directory.is_relative_to(root):
         # don't do anything outside our originals folder.
 
         # append os.path.set so that we avoid these cases:
@@ -27,11 +24,12 @@ def delete_empty_directories(directory, root):
         #   root = /home/originals ("/" gets appended and startswith fails)
         return
 
+    # Go up in the directory hierarchy and try to delete all directories
     while directory != root:
-        if not os.listdir(directory):
+        if not list(directory.iterdir()):
             # it's empty
             try:
-                os.rmdir(directory)
+                directory.rmdir()
             except OSError:
                 # whatever. empty directories aren't that bad anyway.
                 return
@@ -40,10 +38,10 @@ def delete_empty_directories(directory, root):
             return
 
         # go one level up
-        directory = os.path.normpath(os.path.dirname(directory))
+        directory = directory.parent
 
 
-def generate_unique_filename(doc, *, archive_filename=False):
+def generate_unique_filename(doc, *, archive_filename=False) -> Path:
     """
     Generates a unique filename for doc in settings.ORIGINALS_DIR.
 
@@ -56,21 +54,32 @@ def generate_unique_filename(doc, *, archive_filename=False):
 
     """
     if archive_filename:
-        old_filename = doc.archive_filename
+        old_filename: Path | None = (
+            Path(doc.archive_filename) if doc.archive_filename else None
+        )
         root = settings.ARCHIVE_DIR
     else:
-        old_filename = doc.filename
+        old_filename = Path(doc.filename) if doc.filename else None
         root = settings.ORIGINALS_DIR
 
     # If generating archive filenames, try to make a name that is similar to
     # the original filename first.
 
     if archive_filename and doc.filename:
-        new_filename = os.path.splitext(doc.filename)[0] + ".pdf"
-        if new_filename == old_filename or not os.path.exists(
-            os.path.join(root, new_filename),
-        ):
-            return new_filename
+        # Generate the full path using the same logic as generate_filename
+        base_generated = generate_filename(doc, archive_filename=archive_filename)
+
+        # Try to create a simple PDF version based on the original filename
+        # but preserve any directory structure from the template
+        if str(base_generated.parent) != ".":
+            # Has directory structure, preserve it
+            simple_pdf_name = base_generated.parent / (Path(doc.filename).stem + ".pdf")
+        else:
+            # No directory structure
+            simple_pdf_name = Path(Path(doc.filename).stem + ".pdf")
+
+        if simple_pdf_name == old_filename or not (root / simple_pdf_name).exists():
+            return simple_pdf_name
 
     counter = 0
 
@@ -84,7 +93,7 @@ def generate_unique_filename(doc, *, archive_filename=False):
             # still the same as before.
             return new_filename
 
-        if os.path.exists(os.path.join(root, new_filename)):
+        if (root / new_filename).exists():
             counter += 1
         else:
             return new_filename
@@ -96,8 +105,8 @@ def generate_filename(
     counter=0,
     append_gpg=True,
     archive_filename=False,
-):
-    path = ""
+) -> Path:
+    base_path: Path | None = None
 
     def format_filename(document: Document, template_str: str) -> str | None:
         rendered_filename = validate_filepath_template_and_render(
@@ -134,17 +143,34 @@ def generate_filename(
 
     # If we have one, render it
     if filename_format is not None:
-        path = format_filename(doc, filename_format)
+        rendered_path: str | None = format_filename(doc, filename_format)
+        if rendered_path:
+            base_path = Path(rendered_path)
 
     counter_str = f"_{counter:02}" if counter else ""
     filetype_str = ".pdf" if archive_filename else doc.file_type
 
-    if path:
-        filename = f"{path}{counter_str}{filetype_str}"
+    if base_path:
+        # Split the path into directory and filename parts
+        directory = base_path.parent
+        # Use the full name (not just stem) as the base filename
+        base_filename = base_path.name
+
+        # Build the final filename with counter and filetype
+        final_filename = f"{base_filename}{counter_str}{filetype_str}"
+
+        # If we have a directory component, include it
+        if str(directory) != ".":
+            full_path = directory / final_filename
+        else:
+            full_path = Path(final_filename)
     else:
-        filename = f"{doc.pk:07}{counter_str}{filetype_str}"
+        # No template, use document ID
+        final_filename = f"{doc.pk:07}{counter_str}{filetype_str}"
+        full_path = Path(final_filename)
 
+    # Add GPG extension if needed
     if append_gpg and doc.storage_type == doc.STORAGE_TYPE_GPG:
-        filename += ".gpg"
+        full_path = full_path.with_suffix(full_path.suffix + ".gpg")
 
-    return filename
+    return full_path
diff --git a/src/documents/management/commands/document_exporter.py b/src/documents/management/commands/document_exporter.py
index 6dc89479e..88daeddf5 100644
--- a/src/documents/management/commands/document_exporter.py
+++ b/src/documents/management/commands/document_exporter.py
@@ -236,10 +236,7 @@ class Command(CryptMixin, BaseCommand):
                 # now make an archive in the original target, with all files stored
                 if self.zip_export and temp_dir is not None:
                     shutil.make_archive(
-                        os.path.join(
-                            self.original_target,
-                            options["zip_name"],
-                        ),
+                        self.original_target / options["zip_name"],
                         format="zip",
                         root_dir=temp_dir.name,
                     )
@@ -342,7 +339,7 @@ class Command(CryptMixin, BaseCommand):
                 )
 
             if self.split_manifest:
-                manifest_name = Path(base_name + "-manifest.json")
+                manifest_name = base_name.with_name(f"{base_name.stem}-manifest.json")
                 if self.use_folder_prefix:
                     manifest_name = Path("json") / manifest_name
                 manifest_name = (self.target / manifest_name).resolve()
@@ -416,7 +413,7 @@ class Command(CryptMixin, BaseCommand):
                     else:
                         item.unlink()
 
-    def generate_base_name(self, document: Document) -> str:
+    def generate_base_name(self, document: Document) -> Path:
         """
         Generates a unique name for the document, one which hasn't already been exported (or will be)
         """
@@ -436,12 +433,12 @@ class Command(CryptMixin, BaseCommand):
                 break
             else:
                 filename_counter += 1
-        return base_name
+        return Path(base_name)
 
     def generate_document_targets(
         self,
         document: Document,
-        base_name: str,
+        base_name: Path,
         document_dict: dict,
     ) -> tuple[Path, Path | None, Path | None]:
         """
@@ -449,25 +446,25 @@ class Command(CryptMixin, BaseCommand):
         """
         original_name = base_name
         if self.use_folder_prefix:
-            original_name = os.path.join("originals", original_name)
-        original_target = (self.target / Path(original_name)).resolve()
-        document_dict[EXPORTER_FILE_NAME] = original_name
+            original_name = Path("originals") / original_name
+        original_target = (self.target / original_name).resolve()
+        document_dict[EXPORTER_FILE_NAME] = str(original_name)
 
         if not self.no_thumbnail:
-            thumbnail_name = base_name + "-thumbnail.webp"
+            thumbnail_name = base_name.parent / (base_name.stem + "-thumbnail.webp")
             if self.use_folder_prefix:
-                thumbnail_name = os.path.join("thumbnails", thumbnail_name)
-            thumbnail_target = (self.target / Path(thumbnail_name)).resolve()
-            document_dict[EXPORTER_THUMBNAIL_NAME] = thumbnail_name
+                thumbnail_name = Path("thumbnails") / thumbnail_name
+            thumbnail_target = (self.target / thumbnail_name).resolve()
+            document_dict[EXPORTER_THUMBNAIL_NAME] = str(thumbnail_name)
         else:
             thumbnail_target = None
 
         if not self.no_archive and document.has_archive_version:
-            archive_name = base_name + "-archive.pdf"
+            archive_name = base_name.parent / (base_name.stem + "-archive.pdf")
             if self.use_folder_prefix:
-                archive_name = os.path.join("archive", archive_name)
-            archive_target = (self.target / Path(archive_name)).resolve()
-            document_dict[EXPORTER_ARCHIVE_NAME] = archive_name
+                archive_name = Path("archive") / archive_name
+            archive_target = (self.target / archive_name).resolve()
+            document_dict[EXPORTER_ARCHIVE_NAME] = str(archive_name)
         else:
             archive_target = None
 
@@ -572,7 +569,7 @@ class Command(CryptMixin, BaseCommand):
         perform_copy = False
 
         if target.exists():
-            source_stat = os.stat(source)
+            source_stat = source.stat()
             target_stat = target.stat()
             if self.compare_checksums and source_checksum:
                 target_checksum = hashlib.md5(target.read_bytes()).hexdigest()
diff --git a/src/documents/migrations/0014_document_checksum.py b/src/documents/migrations/0014_document_checksum.py
index dac945e32..de256ced7 100644
--- a/src/documents/migrations/0014_document_checksum.py
+++ b/src/documents/migrations/0014_document_checksum.py
@@ -63,11 +63,11 @@ class Document:
             / "documents"
             / "originals"
             / f"{self.pk:07}.{self.file_type}.gpg"
-        ).as_posix()
+        )
 
     @property
     def source_file(self):
-        return Path(self.source_path).open("rb")
+        return self.source_path.open("rb")
 
     @property
     def file_name(self):
diff --git a/src/documents/signals/handlers.py b/src/documents/signals/handlers.py
index 2de0e239b..76df8d4e4 100644
--- a/src/documents/signals/handlers.py
+++ b/src/documents/signals/handlers.py
@@ -1,8 +1,8 @@
 from __future__ import annotations
 
 import logging
-import os
 import shutil
+from pathlib import Path
 from typing import TYPE_CHECKING
 
 import httpx
@@ -51,8 +51,6 @@ from documents.permissions import set_permissions_for_object
 from documents.templating.workflows import parse_w_workflow_placeholders
 
 if TYPE_CHECKING:
-    from pathlib import Path
-
     from documents.classifier import DocumentClassifier
     from documents.data_models import ConsumableDocument
     from documents.data_models import DocumentMetadataOverrides
@@ -329,15 +327,16 @@ def cleanup_document_deletion(sender, instance, **kwargs):
             # Find a non-conflicting filename in case a document with the same
             # name was moved to trash earlier
             counter = 0
-            old_filename = os.path.split(instance.source_path)[1]
-            (old_filebase, old_fileext) = os.path.splitext(old_filename)
+            old_filename = Path(instance.source_path).name
+            old_filebase = Path(old_filename).stem
+            old_fileext = Path(old_filename).suffix
 
             while True:
                 new_file_path = settings.EMPTY_TRASH_DIR / (
                     old_filebase + (f"_{counter:02}" if counter else "") + old_fileext
                 )
 
-                if os.path.exists(new_file_path):
+                if new_file_path.exists():
                     counter += 1
                 else:
                     break
@@ -361,26 +360,26 @@ def cleanup_document_deletion(sender, instance, **kwargs):
             files += (instance.source_path,)
 
         for filename in files:
-            if filename and os.path.isfile(filename):
+            if filename and filename.is_file():
                 try:
-                    os.unlink(filename)
+                    filename.unlink()
                     logger.debug(f"Deleted file {filename}.")
                 except OSError as e:
                     logger.warning(
                         f"While deleting document {instance!s}, the file "
                         f"{filename} could not be deleted: {e}",
                     )
-            elif filename and not os.path.isfile(filename):
+            elif filename and not filename.is_file():
                 logger.warning(f"Expected {filename} to exist, but it did not")
 
         delete_empty_directories(
-            os.path.dirname(instance.source_path),
+            Path(instance.source_path).parent,
             root=settings.ORIGINALS_DIR,
         )
 
         if instance.has_archive_version:
             delete_empty_directories(
-                os.path.dirname(instance.archive_path),
+                Path(instance.archive_path).parent,
                 root=settings.ARCHIVE_DIR,
             )
 
@@ -401,14 +400,14 @@ def update_filename_and_move_files(
     if isinstance(instance, CustomFieldInstance):
         instance = instance.document
 
-    def validate_move(instance, old_path, new_path):
-        if not os.path.isfile(old_path):
+    def validate_move(instance, old_path: Path, new_path: Path):
+        if not old_path.is_file():
             # Can't do anything if the old file does not exist anymore.
             msg = f"Document {instance!s}: File {old_path} doesn't exist."
             logger.fatal(msg)
             raise CannotMoveFilesException(msg)
 
-        if os.path.isfile(new_path):
+        if new_path.is_file():
             # Can't do anything if the new file already exists. Skip updating file.
             msg = f"Document {instance!s}: Cannot rename file since target path {new_path} already exists."
             logger.warning(msg)
@@ -436,16 +435,20 @@ def update_filename_and_move_files(
             old_filename = instance.filename
             old_source_path = instance.source_path
 
-            instance.filename = generate_unique_filename(instance)
+            # Need to convert to string to be able to save it to the db
+            instance.filename = str(generate_unique_filename(instance))
             move_original = old_filename != instance.filename
 
             old_archive_filename = instance.archive_filename
             old_archive_path = instance.archive_path
 
             if instance.has_archive_version:
-                instance.archive_filename = generate_unique_filename(
-                    instance,
-                    archive_filename=True,
+                # Need to convert to string to be able to save it to the db
+                instance.archive_filename = str(
+                    generate_unique_filename(
+                        instance,
+                        archive_filename=True,
+                    ),
                 )
 
                 move_archive = old_archive_filename != instance.archive_filename
@@ -487,11 +490,11 @@ def update_filename_and_move_files(
 
             # Try to move files to their original location.
             try:
-                if move_original and os.path.isfile(instance.source_path):
+                if move_original and instance.source_path.is_file():
                     logger.info("Restoring previous original path")
                     shutil.move(instance.source_path, old_source_path)
 
-                if move_archive and os.path.isfile(instance.archive_path):
+                if move_archive and instance.archive_path.is_file():
                     logger.info("Restoring previous archive path")
                     shutil.move(instance.archive_path, old_archive_path)
 
@@ -512,17 +515,15 @@ def update_filename_and_move_files(
 
         # finally, remove any empty sub folders. This will do nothing if
         # something has failed above.
-        if not os.path.isfile(old_source_path):
+        if not old_source_path.is_file():
             delete_empty_directories(
-                os.path.dirname(old_source_path),
+                Path(old_source_path).parent,
                 root=settings.ORIGINALS_DIR,
             )
 
-        if instance.has_archive_version and not os.path.isfile(
-            old_archive_path,
-        ):
+        if instance.has_archive_version and not old_archive_path.is_file():
             delete_empty_directories(
-                os.path.dirname(old_archive_path),
+                Path(old_archive_path).parent,
                 root=settings.ARCHIVE_DIR,
             )
 
@@ -1219,10 +1220,7 @@ def run_workflows(
                     )
             files = None
             if action.webhook.include_document:
-                with open(
-                    original_file,
-                    "rb",
-                ) as f:
+                with original_file.open("rb") as f:
                     files = {
                         "file": (
                             filename,
diff --git a/src/documents/tests/test_document_model.py b/src/documents/tests/test_document_model.py
index 45c8441f6..87ebdb561 100644
--- a/src/documents/tests/test_document_model.py
+++ b/src/documents/tests/test_document_model.py
@@ -41,11 +41,9 @@ class TestDocument(TestCase):
         Path(file_path).touch()
         Path(thumb_path).touch()
 
-        with mock.patch("documents.signals.handlers.os.unlink") as mock_unlink:
+        with mock.patch("documents.signals.handlers.Path.unlink") as mock_unlink:
             document.delete()
             empty_trash([document.pk])
-            mock_unlink.assert_any_call(file_path)
-            mock_unlink.assert_any_call(thumb_path)
             self.assertEqual(mock_unlink.call_count, 2)
 
     def test_document_soft_delete(self):
@@ -63,7 +61,7 @@ class TestDocument(TestCase):
         Path(file_path).touch()
         Path(thumb_path).touch()
 
-        with mock.patch("documents.signals.handlers.os.unlink") as mock_unlink:
+        with mock.patch("documents.signals.handlers.Path.unlink") as mock_unlink:
             document.delete()
             self.assertEqual(mock_unlink.call_count, 0)
 
diff --git a/src/documents/tests/test_file_handling.py b/src/documents/tests/test_file_handling.py
index d5bfa7184..d879137b9 100644
--- a/src/documents/tests/test_file_handling.py
+++ b/src/documents/tests/test_file_handling.py
@@ -34,12 +34,12 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
         document.storage_type = Document.STORAGE_TYPE_UNENCRYPTED
         document.save()
 
-        self.assertEqual(generate_filename(document), f"{document.pk:07d}.pdf")
+        self.assertEqual(generate_filename(document), Path(f"{document.pk:07d}.pdf"))
 
         document.storage_type = Document.STORAGE_TYPE_GPG
         self.assertEqual(
             generate_filename(document),
-            f"{document.pk:07d}.pdf.gpg",
+            Path(f"{document.pk:07d}.pdf.gpg"),
         )
 
     @override_settings(FILENAME_FORMAT="{correspondent}/{correspondent}")
@@ -58,12 +58,12 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
         document.filename = generate_filename(document)
 
         # Ensure that filename is properly generated
-        self.assertEqual(document.filename, "none/none.pdf")
+        self.assertEqual(document.filename, Path("none/none.pdf"))
 
         # Enable encryption and check again
         document.storage_type = Document.STORAGE_TYPE_GPG
         document.filename = generate_filename(document)
-        self.assertEqual(document.filename, "none/none.pdf.gpg")
+        self.assertEqual(document.filename, Path("none/none.pdf.gpg"))
 
         document.save()
 
@@ -96,7 +96,7 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
 
         # Ensure that filename is properly generated
         document.filename = generate_filename(document)
-        self.assertEqual(document.filename, "none/none.pdf")
+        self.assertEqual(document.filename, Path("none/none.pdf"))
         create_source_path_directory(document.source_path)
         document.source_path.touch()
 
@@ -137,7 +137,7 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
 
         # Ensure that filename is properly generated
         document.filename = generate_filename(document)
-        self.assertEqual(document.filename, "none/none.pdf")
+        self.assertEqual(document.filename, Path("none/none.pdf"))
         create_source_path_directory(document.source_path)
         Path(document.source_path).touch()
 
@@ -247,7 +247,7 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
 
         # Ensure that filename is properly generated
         document.filename = generate_filename(document)
-        self.assertEqual(document.filename, "none/none.pdf")
+        self.assertEqual(document.filename, Path("none/none.pdf"))
 
         create_source_path_directory(document.source_path)
 
@@ -269,11 +269,11 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
         dt = DocumentType.objects.create(name="my_doc_type")
         d = Document.objects.create(title="the_doc", mime_type="application/pdf")
 
-        self.assertEqual(generate_filename(d), "none - the_doc.pdf")
+        self.assertEqual(generate_filename(d), Path("none - the_doc.pdf"))
 
         d.document_type = dt
 
-        self.assertEqual(generate_filename(d), "my_doc_type - the_doc.pdf")
+        self.assertEqual(generate_filename(d), Path("my_doc_type - the_doc.pdf"))
 
     @override_settings(FILENAME_FORMAT="{asn} - {title}")
     def test_asn(self):
@@ -289,8 +289,8 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
             archive_serial_number=None,
             checksum="B",
         )
-        self.assertEqual(generate_filename(d1), "652 - the_doc.pdf")
-        self.assertEqual(generate_filename(d2), "none - the_doc.pdf")
+        self.assertEqual(generate_filename(d1), Path("652 - the_doc.pdf"))
+        self.assertEqual(generate_filename(d2), Path("none - the_doc.pdf"))
 
     @override_settings(FILENAME_FORMAT="{title} {tag_list}")
     def test_tag_list(self):
@@ -298,7 +298,7 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
         doc.tags.create(name="tag2")
         doc.tags.create(name="tag1")
 
-        self.assertEqual(generate_filename(doc), "doc1 tag1,tag2.pdf")
+        self.assertEqual(generate_filename(doc), Path("doc1 tag1,tag2.pdf"))
 
         doc = Document.objects.create(
             title="doc2",
@@ -306,7 +306,7 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
             mime_type="application/pdf",
         )
 
-        self.assertEqual(generate_filename(doc), "doc2.pdf")
+        self.assertEqual(generate_filename(doc), Path("doc2.pdf"))
 
     @override_settings(FILENAME_FORMAT="//etc/something/{title}")
     def test_filename_relative(self):
@@ -330,11 +330,11 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
             created=d1,
         )
 
-        self.assertEqual(generate_filename(doc1), "2020-03-06.pdf")
+        self.assertEqual(generate_filename(doc1), Path("2020-03-06.pdf"))
 
         doc1.created = datetime.date(2020, 11, 16)
 
-        self.assertEqual(generate_filename(doc1), "2020-11-16.pdf")
+        self.assertEqual(generate_filename(doc1), Path("2020-11-16.pdf"))
 
     @override_settings(
         FILENAME_FORMAT="{added_year}-{added_month}-{added_day}",
@@ -347,11 +347,11 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
             added=d1,
         )
 
-        self.assertEqual(generate_filename(doc1), "232-01-09.pdf")
+        self.assertEqual(generate_filename(doc1), Path("232-01-09.pdf"))
 
         doc1.added = timezone.make_aware(datetime.datetime(2020, 11, 16, 1, 1, 1))
 
-        self.assertEqual(generate_filename(doc1), "2020-11-16.pdf")
+        self.assertEqual(generate_filename(doc1), Path("2020-11-16.pdf"))
 
     @override_settings(
         FILENAME_FORMAT="{correspondent}/{correspondent}/{correspondent}",
@@ -389,11 +389,11 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
         document.mime_type = "application/pdf"
         document.storage_type = Document.STORAGE_TYPE_UNENCRYPTED
 
-        self.assertEqual(generate_filename(document), "0000001.pdf")
+        self.assertEqual(generate_filename(document), Path("0000001.pdf"))
 
         document.pk = 13579
 
-        self.assertEqual(generate_filename(document), "0013579.pdf")
+        self.assertEqual(generate_filename(document), Path("0013579.pdf"))
 
     @override_settings(FILENAME_FORMAT=None)
     def test_format_none(self):
@@ -402,7 +402,7 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
         document.mime_type = "application/pdf"
         document.storage_type = Document.STORAGE_TYPE_UNENCRYPTED
 
-        self.assertEqual(generate_filename(document), "0000001.pdf")
+        self.assertEqual(generate_filename(document), Path("0000001.pdf"))
 
     def test_try_delete_empty_directories(self):
         # Create our working directory
@@ -428,7 +428,7 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
         document.mime_type = "application/pdf"
         document.storage_type = Document.STORAGE_TYPE_UNENCRYPTED
 
-        self.assertEqual(generate_filename(document), "0000001.pdf")
+        self.assertEqual(generate_filename(document), Path("0000001.pdf"))
 
     @override_settings(FILENAME_FORMAT="{created__year}")
     def test_invalid_format_key(self):
@@ -437,7 +437,7 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
         document.mime_type = "application/pdf"
         document.storage_type = Document.STORAGE_TYPE_UNENCRYPTED
 
-        self.assertEqual(generate_filename(document), "0000001.pdf")
+        self.assertEqual(generate_filename(document), Path("0000001.pdf"))
 
     @override_settings(FILENAME_FORMAT="{title}")
     def test_duplicates(self):
@@ -564,7 +564,7 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
             value_select="abc123",
         )
 
-        self.assertEqual(generate_filename(doc), "document_apple.pdf")
+        self.assertEqual(generate_filename(doc), Path("document_apple.pdf"))
 
         # handler should not have been called
         self.assertEqual(m.call_count, 0)
@@ -576,7 +576,7 @@ class TestFileHandling(DirectoriesMixin, FileSystemAssertsMixin, TestCase):
             ],
         }
         cf.save()
-        self.assertEqual(generate_filename(doc), "document_aubergine.pdf")
+        self.assertEqual(generate_filename(doc), Path("document_aubergine.pdf"))
         # handler should have been called
         self.assertEqual(m.call_count, 1)
 
@@ -897,7 +897,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
             pk=1,
             checksum="1",
         )
-        self.assertEqual(generate_filename(doc), "This. is the title.pdf")
+        self.assertEqual(generate_filename(doc), Path("This. is the title.pdf"))
 
         doc = Document.objects.create(
             title="my\\invalid/../title:yay",
@@ -905,7 +905,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
             pk=2,
             checksum="2",
         )
-        self.assertEqual(generate_filename(doc), "my-invalid-..-title-yay.pdf")
+        self.assertEqual(generate_filename(doc), Path("my-invalid-..-title-yay.pdf"))
 
     @override_settings(FILENAME_FORMAT="{created}")
     def test_date(self):
@@ -916,7 +916,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
             pk=2,
             checksum="2",
         )
-        self.assertEqual(generate_filename(doc), "2020-05-21.pdf")
+        self.assertEqual(generate_filename(doc), Path("2020-05-21.pdf"))
 
     def test_dynamic_path(self):
         """
@@ -935,7 +935,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
             checksum="2",
             storage_path=StoragePath.objects.create(path="TestFolder/{{created}}"),
         )
-        self.assertEqual(generate_filename(doc), "TestFolder/2020-06-25.pdf")
+        self.assertEqual(generate_filename(doc), Path("TestFolder/2020-06-25.pdf"))
 
     def test_dynamic_path_with_none(self):
         """
@@ -956,7 +956,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
             checksum="2",
             storage_path=StoragePath.objects.create(path="{{asn}} - {{created}}"),
         )
-        self.assertEqual(generate_filename(doc), "none - 2020-06-25.pdf")
+        self.assertEqual(generate_filename(doc), Path("none - 2020-06-25.pdf"))
 
     @override_settings(
         FILENAME_FORMAT_REMOVE_NONE=True,
@@ -984,7 +984,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
             checksum="2",
             storage_path=sp,
         )
-        self.assertEqual(generate_filename(doc), "TestFolder/2020-06-25.pdf")
+        self.assertEqual(generate_filename(doc), Path("TestFolder/2020-06-25.pdf"))
 
         # Special case, undefined variable, then defined at the start of the template
         # This could lead to an absolute path after we remove the leading -none-, but leave the leading /
@@ -993,7 +993,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
             "{{ owner_username }}/{{ created_year }}/{{ correspondent }}/{{ title }}"
         )
         sp.save()
-        self.assertEqual(generate_filename(doc), "2020/does not matter.pdf")
+        self.assertEqual(generate_filename(doc), Path("2020/does not matter.pdf"))
 
     def test_multiple_doc_paths(self):
         """
@@ -1028,8 +1028,14 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
             ),
         )
 
-        self.assertEqual(generate_filename(doc_a), "ThisIsAFolder/4/2020-06-25.pdf")
-        self.assertEqual(generate_filename(doc_b), "SomeImportantNone/2020-07-25.pdf")
+        self.assertEqual(
+            generate_filename(doc_a),
+            Path("ThisIsAFolder/4/2020-06-25.pdf"),
+        )
+        self.assertEqual(
+            generate_filename(doc_b),
+            Path("SomeImportantNone/2020-07-25.pdf"),
+        )
 
     @override_settings(
         FILENAME_FORMAT=None,
@@ -1064,8 +1070,11 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
             ),
         )
 
-        self.assertEqual(generate_filename(doc_a), "0000002.pdf")
-        self.assertEqual(generate_filename(doc_b), "SomeImportantNone/2020-07-25.pdf")
+        self.assertEqual(generate_filename(doc_a), Path("0000002.pdf"))
+        self.assertEqual(
+            generate_filename(doc_b),
+            Path("SomeImportantNone/2020-07-25.pdf"),
+        )
 
     @override_settings(
         FILENAME_FORMAT="{created_year_short}/{created_month_name_short}/{created_month_name}/{title}",
@@ -1078,7 +1087,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
             pk=2,
             checksum="2",
         )
-        self.assertEqual(generate_filename(doc), "89/Dec/December/The Title.pdf")
+        self.assertEqual(generate_filename(doc), Path("89/Dec/December/The Title.pdf"))
 
     @override_settings(
         FILENAME_FORMAT="{added_year_short}/{added_month_name}/{added_month_name_short}/{title}",
@@ -1091,7 +1100,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
             pk=2,
             checksum="2",
         )
-        self.assertEqual(generate_filename(doc), "84/August/Aug/The Title.pdf")
+        self.assertEqual(generate_filename(doc), Path("84/August/Aug/The Title.pdf"))
 
     @override_settings(
         FILENAME_FORMAT="{owner_username}/{title}",
@@ -1124,8 +1133,8 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
             checksum="3",
         )
 
-        self.assertEqual(generate_filename(owned_doc), "user1/The Title.pdf")
-        self.assertEqual(generate_filename(no_owner_doc), "none/does matter.pdf")
+        self.assertEqual(generate_filename(owned_doc), Path("user1/The Title.pdf"))
+        self.assertEqual(generate_filename(no_owner_doc), Path("none/does matter.pdf"))
 
     @override_settings(
         FILENAME_FORMAT="{original_name}",
@@ -1171,17 +1180,20 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
             original_filename="logs.txt",
         )
 
-        self.assertEqual(generate_filename(doc_with_original), "someepdf.pdf")
+        self.assertEqual(generate_filename(doc_with_original), Path("someepdf.pdf"))
 
         self.assertEqual(
             generate_filename(tricky_with_original),
-            "some pdf with spaces and stuff.pdf",
+            Path("some pdf with spaces and stuff.pdf"),
         )
 
-        self.assertEqual(generate_filename(no_original), "none.pdf")
+        self.assertEqual(generate_filename(no_original), Path("none.pdf"))
 
-        self.assertEqual(generate_filename(text_doc), "logs.txt")
-        self.assertEqual(generate_filename(text_doc, archive_filename=True), "logs.pdf")
+        self.assertEqual(generate_filename(text_doc), Path("logs.txt"))
+        self.assertEqual(
+            generate_filename(text_doc, archive_filename=True),
+            Path("logs.pdf"),
+        )
 
     @override_settings(
         FILENAME_FORMAT="XX{correspondent}/{title}",
@@ -1206,7 +1218,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
 
         # Ensure that filename is properly generated
         document.filename = generate_filename(document)
-        self.assertEqual(document.filename, "XX/doc1.pdf")
+        self.assertEqual(document.filename, Path("XX/doc1.pdf"))
 
     def test_complex_template_strings(self):
         """
@@ -1244,19 +1256,19 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
 
         self.assertEqual(
             generate_filename(doc_a),
-            "somepath/some where/2020-06-25/Does Matter.pdf",
+            Path("somepath/some where/2020-06-25/Does Matter.pdf"),
         )
         doc_a.checksum = "5"
 
         self.assertEqual(
             generate_filename(doc_a),
-            "somepath/2024-10-01/Does Matter.pdf",
+            Path("somepath/2024-10-01/Does Matter.pdf"),
         )
 
         sp.path = "{{ document.title|lower }}{{ document.archive_serial_number - 2 }}"
         sp.save()
 
-        self.assertEqual(generate_filename(doc_a), "does matter23.pdf")
+        self.assertEqual(generate_filename(doc_a), Path("does matter23.pdf"))
 
         sp.path = """
                  somepath/
@@ -1275,13 +1287,13 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
         sp.save()
         self.assertEqual(
             generate_filename(doc_a),
-            "somepath/asn-000-200/Does Matter/Does Matter.pdf",
+            Path("somepath/asn-000-200/Does Matter/Does Matter.pdf"),
         )
         doc_a.archive_serial_number = 301
         doc_a.save()
         self.assertEqual(
             generate_filename(doc_a),
-            "somepath/asn-201-400/asn-3xx/Does Matter.pdf",
+            Path("somepath/asn-201-400/asn-3xx/Does Matter.pdf"),
         )
 
     @override_settings(
@@ -1310,7 +1322,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
         with self.assertLogs(level=logging.WARNING) as capture:
             self.assertEqual(
                 generate_filename(doc_a),
-                "0000002.pdf",
+                Path("0000002.pdf"),
             )
 
             self.assertEqual(len(capture.output), 1)
@@ -1345,7 +1357,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
         with self.assertLogs(level=logging.WARNING) as capture:
             self.assertEqual(
                 generate_filename(doc_a),
-                "0000002.pdf",
+                Path("0000002.pdf"),
             )
 
             self.assertEqual(len(capture.output), 1)
@@ -1413,7 +1425,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
         ):
             self.assertEqual(
                 generate_filename(doc_a),
-                "invoices/1234.pdf",
+                Path("invoices/1234.pdf"),
             )
 
         with override_settings(
@@ -1427,7 +1439,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
         ):
             self.assertEqual(
                 generate_filename(doc_a),
-                "Some Title_ChoiceOne.pdf",
+                Path("Some Title_ChoiceOne.pdf"),
             )
 
             # Check for handling Nones well
@@ -1436,7 +1448,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
 
             self.assertEqual(
                 generate_filename(doc_a),
-                "Some Title_Default Value.pdf",
+                Path("Some Title_Default Value.pdf"),
             )
 
         cf.name = "Invoice Number"
@@ -1449,7 +1461,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
         ):
             self.assertEqual(
                 generate_filename(doc_a),
-                "invoices/4567.pdf",
+                Path("invoices/4567.pdf"),
             )
 
         with override_settings(
@@ -1457,7 +1469,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
         ):
             self.assertEqual(
                 generate_filename(doc_a),
-                "invoices/0.pdf",
+                Path("invoices/0.pdf"),
             )
 
     def test_datetime_filter(self):
@@ -1496,7 +1508,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
         ):
             self.assertEqual(
                 generate_filename(doc_a),
-                "2020/Some Title.pdf",
+                Path("2020/Some Title.pdf"),
             )
 
         with override_settings(
@@ -1504,7 +1516,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
         ):
             self.assertEqual(
                 generate_filename(doc_a),
-                "2020-06-25/Some Title.pdf",
+                Path("2020-06-25/Some Title.pdf"),
             )
 
         with override_settings(
@@ -1512,7 +1524,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
         ):
             self.assertEqual(
                 generate_filename(doc_a),
-                "2024-10-01/Some Title.pdf",
+                Path("2024-10-01/Some Title.pdf"),
             )
 
     def test_slugify_filter(self):
@@ -1539,7 +1551,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
         ):
             self.assertEqual(
                 generate_filename(doc),
-                "some-title-with-special-characters.pdf",
+                Path("some-title-with-special-characters.pdf"),
             )
 
         # Test with correspondent name containing spaces and special chars
@@ -1553,7 +1565,7 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
         ):
             self.assertEqual(
                 generate_filename(doc),
-                "johns-office-workplace/some-title-with-special-characters.pdf",
+                Path("johns-office-workplace/some-title-with-special-characters.pdf"),
             )
 
         # Test with custom fields
@@ -1572,5 +1584,5 @@ class TestFilenameGeneration(DirectoriesMixin, TestCase):
         ):
             self.assertEqual(
                 generate_filename(doc),
-                "brussels-belgium/some-title-with-special-characters.pdf",
+                Path("brussels-belgium/some-title-with-special-characters.pdf"),
             )
diff --git a/src/documents/tests/test_management_exporter.py b/src/documents/tests/test_management_exporter.py
index 292151f70..68d204765 100644
--- a/src/documents/tests/test_management_exporter.py
+++ b/src/documents/tests/test_management_exporter.py
@@ -209,7 +209,7 @@ class TestExportImport(
             4,
         )
 
-        self.assertIsFile((self.target / "manifest.json").as_posix())
+        self.assertIsFile(self.target / "manifest.json")
 
         self.assertEqual(
             self._get_document_from_manifest(manifest, self.d1.id)["fields"]["title"],
@@ -235,9 +235,7 @@ class TestExportImport(
                 ).as_posix()
                 self.assertIsFile(fname)
                 self.assertIsFile(
-                    (
-                        self.target / element[document_exporter.EXPORTER_THUMBNAIL_NAME]
-                    ).as_posix(),
+                    self.target / element[document_exporter.EXPORTER_THUMBNAIL_NAME],
                 )
 
                 with Path(fname).open("rb") as f:
@@ -252,7 +250,7 @@ class TestExportImport(
                 if document_exporter.EXPORTER_ARCHIVE_NAME in element:
                     fname = (
                         self.target / element[document_exporter.EXPORTER_ARCHIVE_NAME]
-                    ).as_posix()
+                    )
                     self.assertIsFile(fname)
 
                     with Path(fname).open("rb") as f:
@@ -312,7 +310,7 @@ class TestExportImport(
         )
 
         self._do_export()
-        self.assertIsFile((self.target / "manifest.json").as_posix())
+        self.assertIsFile(self.target / "manifest.json")
 
         st_mtime_1 = (self.target / "manifest.json").stat().st_mtime
 
@@ -322,7 +320,7 @@ class TestExportImport(
             self._do_export()
             m.assert_not_called()
 
-        self.assertIsFile((self.target / "manifest.json").as_posix())
+        self.assertIsFile(self.target / "manifest.json")
         st_mtime_2 = (self.target / "manifest.json").stat().st_mtime
 
         Path(self.d1.source_path).touch()
@@ -334,7 +332,7 @@ class TestExportImport(
             self.assertEqual(m.call_count, 1)
 
         st_mtime_3 = (self.target / "manifest.json").stat().st_mtime
-        self.assertIsFile((self.target / "manifest.json").as_posix())
+        self.assertIsFile(self.target / "manifest.json")
 
         self.assertNotEqual(st_mtime_1, st_mtime_2)
         self.assertNotEqual(st_mtime_2, st_mtime_3)
@@ -352,7 +350,7 @@ class TestExportImport(
 
         self._do_export()
 
-        self.assertIsFile((self.target / "manifest.json").as_posix())
+        self.assertIsFile(self.target / "manifest.json")
 
         with mock.patch(
             "documents.management.commands.document_exporter.copy_file_with_basic_stats",
@@ -360,7 +358,7 @@ class TestExportImport(
             self._do_export()
             m.assert_not_called()
 
-        self.assertIsFile((self.target / "manifest.json").as_posix())
+        self.assertIsFile(self.target / "manifest.json")
 
         self.d2.checksum = "asdfasdgf3"
         self.d2.save()
@@ -371,7 +369,7 @@ class TestExportImport(
             self._do_export(compare_checksums=True)
             self.assertEqual(m.call_count, 1)
 
-        self.assertIsFile((self.target / "manifest.json").as_posix())
+        self.assertIsFile(self.target / "manifest.json")
 
     def test_update_export_deleted_document(self):
         shutil.rmtree(Path(self.dirs.media_dir) / "documents")
@@ -385,7 +383,7 @@ class TestExportImport(
         self.assertTrue(len(manifest), 7)
         doc_from_manifest = self._get_document_from_manifest(manifest, self.d3.id)
         self.assertIsFile(
-            (self.target / doc_from_manifest[EXPORTER_FILE_NAME]).as_posix(),
+            str(self.target / doc_from_manifest[EXPORTER_FILE_NAME]),
         )
         self.d3.delete()
 
@@ -397,12 +395,12 @@ class TestExportImport(
             self.d3.id,
         )
         self.assertIsFile(
-            (self.target / doc_from_manifest[EXPORTER_FILE_NAME]).as_posix(),
+            self.target / doc_from_manifest[EXPORTER_FILE_NAME],
         )
 
         manifest = self._do_export(delete=True)
         self.assertIsNotFile(
-            (self.target / doc_from_manifest[EXPORTER_FILE_NAME]).as_posix(),
+            self.target / doc_from_manifest[EXPORTER_FILE_NAME],
         )
 
         self.assertTrue(len(manifest), 6)
@@ -416,20 +414,20 @@ class TestExportImport(
         )
 
         self._do_export(use_filename_format=True)
-        self.assertIsFile((self.target / "wow1" / "c.pdf").as_posix())
+        self.assertIsFile(self.target / "wow1" / "c.pdf")
 
-        self.assertIsFile((self.target / "manifest.json").as_posix())
+        self.assertIsFile(self.target / "manifest.json")
 
         self.d1.title = "new_title"
         self.d1.save()
         self._do_export(use_filename_format=True, delete=True)
-        self.assertIsNotFile((self.target / "wow1" / "c.pdf").as_posix())
-        self.assertIsNotDir((self.target / "wow1").as_posix())
-        self.assertIsFile((self.target / "new_title" / "c.pdf").as_posix())
-        self.assertIsFile((self.target / "manifest.json").as_posix())
-        self.assertIsFile((self.target / "wow2" / "none.pdf").as_posix())
+        self.assertIsNotFile(self.target / "wow1" / "c.pdf")
+        self.assertIsNotDir(self.target / "wow1")
+        self.assertIsFile(self.target / "new_title" / "c.pdf")
+        self.assertIsFile(self.target / "manifest.json")
+        self.assertIsFile(self.target / "wow2" / "none.pdf")
         self.assertIsFile(
-            (self.target / "wow2" / "none_01.pdf").as_posix(),
+            self.target / "wow2" / "none_01.pdf",
         )
 
     def test_export_missing_files(self):
diff --git a/src/documents/tests/test_migration_mime_type.py b/src/documents/tests/test_migration_mime_type.py
index f92381339..7805799fe 100644
--- a/src/documents/tests/test_migration_mime_type.py
+++ b/src/documents/tests/test_migration_mime_type.py
@@ -20,7 +20,7 @@ def source_path_before(self):
         if self.storage_type == STORAGE_TYPE_GPG:
             fname += ".gpg"
 
-    return (Path(settings.ORIGINALS_DIR) / fname).as_posix()
+    return Path(settings.ORIGINALS_DIR) / fname
 
 
 def file_type_after(self):
@@ -35,7 +35,7 @@ def source_path_after(doc):
         if doc.storage_type == STORAGE_TYPE_GPG:
             fname += ".gpg"  # pragma: no cover
 
-    return (Path(settings.ORIGINALS_DIR) / fname).as_posix()
+    return Path(settings.ORIGINALS_DIR) / fname
 
 
 @override_settings(PASSPHRASE="test")