diff --git a/tubesync/common/utils.py b/tubesync/common/utils.py
index b0236e7c7..141b65a93 100644
--- a/tubesync/common/utils.py
+++ b/tubesync/common/utils.py
@@ -209,7 +209,7 @@ def parse_database_connection_string(database_connection_string):
                                       f'as a database connection string: {e}') from e
     driver = parts.scheme
     user_pass_host_port = parts.netloc
-    database = parts.path
+    database = parts.path.removeprefix('/')
     if driver not in valid_drivers:
         raise DatabaseConnectionError(f'Database connection string '
                                       f'"{database_connection_string}" specified an '
@@ -220,6 +220,8 @@ def parse_database_connection_string(database_connection_string):
     if len(host_parts) != 2 or len(user_pass_parts) != 2:
         raise DatabaseConnectionError('Database connection string netloc must be in '
                                       'the format of user:pass@host')
+    # user_pass never used
+    # ruff: ignore[RUF059]
     user_pass, host_port = host_parts
     username, password = user_pass_parts
     host_port_parts = host_port.split(':')
@@ -244,8 +246,6 @@ def parse_database_connection_string(database_connection_string):
         # Malformed
         raise DatabaseConnectionError('Database connection host must be a hostname or '
                                       'a hostname:port combination')
-    if database.startswith('/'):
-        database = database[1:]
     if not database:
         raise DatabaseConnectionError('Database connection string path must be a '
                                       'string in the format of /databasename')    
@@ -284,9 +284,9 @@ def append_uri_params(uri, params):
     return urlunsplit(('', '', uri, qs, ''))
 
 
-def clean_filename(filename):
+def clean_filename(filename: str) -> str:
     if not isinstance(filename, str):
-        raise ValueError(f'filename must be a str, got {type(filename)}')
+        raise TypeError(f'filename must be a str, got {type(filename)}')
     to_scrub = r'<>\/:*?"|%'
     for char in list(to_scrub):
         filename = filename.replace(char, '')
@@ -299,19 +299,58 @@ def clean_filename(filename):
     return clean_filename.strip()
 
 
-def clean_emoji(s):
+def clean_emoji(s: str) -> str:
     if not isinstance(s, str):
-        raise ValueError(f'parameter must be a str, got {type(s)}')
+        raise TypeError(f'parameter must be a str, got {type(s)}')
     return emoji.replace_emoji(s)
 
 
+def truncate_filename(filename: str, *, max_bytes=216, encoding='utf-8') -> str:
+    '''
+        Shortens a filename to fit within `max_bytes` bytes (not characters)
+        while keeping its extension intact. Filesystems limit name length in
+        bytes (commonly 255), so multi-byte titles can exceed the limit with
+        far fewer characters (see issue #522). The default budget leaves
+        headroom for prefixes/suffixes appended later (e.g. `.fNNN`,
+        `.part-FragNN` fragments written by yt-dlp during downloads).
+
+        Bytes are removed from the middle of the stem, keeping its start
+        (usually the beginning of the title) and its end (usually unique
+        suffixes such as the media key and format details, e.g.
+        `{title_full}_{key}_{format}` from the default media format), joined
+        by `_..._`. Truncation never splits a multi-byte character: partial
+        trailing/leading sequences are dropped when decoding.
+    '''
+    max_bytes = max(96, min(232, max_bytes))
+    if not isinstance(filename, str):
+        raise TypeError(f'filename must be a str, got {type(filename)}')
+    if len(filename.encode(encoding)) <= max_bytes:
+        return filename
+    path = Path(filename)
+    name, ext = clean_filename(path.stem), clean_filename(path.suffix)
+    ext_bytes = ext.encode(encoding)
+    if len(ext_bytes) >= max_bytes:
+        # Pathological extension; fall back to a plain byte cut
+        name, ext_bytes = filename, b''
+    marker = '_..._'
+    stem_budget = max_bytes - len(ext_bytes) - len(marker.encode(encoding))
+    stem_bytes = name.encode(encoding)
+    # Keep the unique suffixes at the end of the stem intact (up to a third of
+    # the bytes limit), then fill the rest from the front.
+    tail_keep = min(stem_budget // 2, max_bytes // 3)
+    head_keep = stem_budget - tail_keep
+    head = stem_bytes[:head_keep].decode(encoding, errors='ignore').rstrip()
+    tail = stem_bytes[-tail_keep:].decode(encoding, errors='ignore').lstrip()
+    return head + marker + tail + ext_bytes.decode(encoding)
+
+
 def seconds_to_timestr(seconds):
     seconds = seconds % (24 * 3600)
     hour = seconds // 3600
     seconds %= 3600
     minutes = seconds // 60
     seconds %= 60
-    return '{:02d}:{:02d}:{:02d}'.format(hour, minutes, seconds)
+    return f'{hour:02d}:{minutes:02d}:{seconds:02d}'
 
 
 def time_func(func):
diff --git a/tubesync/sync/models/media.py b/tubesync/sync/models/media.py
index 1c0c0acee..26f78dce2 100644
--- a/tubesync/sync/models/media.py
+++ b/tubesync/sync/models/media.py
@@ -5,6 +5,7 @@
 from copy import deepcopy
 from datetime import datetime, timedelta, timezone as tz
 from pathlib import Path
+from typing import ClassVar
 from xml.etree import ElementTree
 from django.conf import settings
 from django.db import models
@@ -19,6 +20,7 @@
 from common.utils import (
     clean_filename, clean_emoji, directory_and_stem,
     glob_quote, mkdir_p, seconds_to_timestr,
+    truncate_filename,
 )
 from ..youtube import (
     get_media_info as get_youtube_media_info,
@@ -45,6 +47,8 @@
 )
 from .source import Source
 
+# ruff: file-ignore[B010,RUF059,SIM118]
+
 
 class Media(models.Model):
     '''
@@ -56,14 +60,14 @@ class Media(models.Model):
     posix_epoch = datetime(1970, 1, 1, tzinfo=tz.utc)
 
     # Format to use to display a URL for the media
-    URLS = _srctype_dict('https://www.youtube.com/watch?v={key}')
+    URLS: ClassVar[dict[str, str]] = _srctype_dict('https://www.youtube.com/watch?v={key}')
 
     # Callback functions to get a list of media from the source
-    INDEXERS = _srctype_dict(get_youtube_media_info)
+    INDEXERS: ClassVar[dict[str, type(get_youtube_media_info)]] = _srctype_dict(get_youtube_media_info)
 
     # Maps standardised names to names used in source metdata
     _same_name = lambda n, k=None: {k or n: _srctype_dict(n) }
-    METADATA_FIELDS = {
+    METADATA_FIELDS: ClassVar[dict[str, dict[str, str]]] = {
         **(_same_name('upload_date')),
         **(_same_name('timestamp')),
         **(_same_name('title')),
@@ -80,7 +84,7 @@ class Media(models.Model):
         **(_same_name('playlist_title')),
     }
 
-    STATE_ICONS = dict(zip(
+    STATE_ICONS: ClassVar[dict[str, str]] = dict(zip(
         MediaState.values,
         (
             '<i class="far fa-question-circle" title="Unknown download state"></i>',
@@ -596,14 +600,17 @@ def metadata_clear(self, /, *, save=False):
             self.save()
 
 
-    def metadata_dumps(self, arg_dict=dict()):
+    def metadata_dumps(self, arg_dict=None):
         fallback = dict()
         try:
             fallback.update(self.new_metadata.with_formats)
         except ObjectDoesNotExist:
             pass
-        data = arg_dict or fallback
-        return json.dumps(data, separators=(',', ':'), cls=JSONEncoder)
+        return json.dumps(
+            arg_dict or fallback,
+            separators=(',', ':'),
+            cls=JSONEncoder,
+        )
 
 
     def metadata_loads(self, arg_str='{}'):
@@ -646,7 +653,6 @@ def save_to_metadata(self, key, value, /):
             migrated['_using_table'] = True
             self.metadata = self.metadata_dumps(arg_dict=migrated)
             self.save()
-        from common.logger import log
         log.debug(f'Saved to metadata: {self.key} / {self.uuid}: {key=}: {value}')
 
 
@@ -677,11 +683,10 @@ def reduce_data(self):
             filtered_data = filter_response(data, True)
             filtered_data['_reduce_data_ran_at'] = round((now - self.posix_epoch).total_seconds())
             filtered_json = self.metadata_dumps(arg_dict=filtered_data)
-        except Exception as e:
-            from common.logger import log
-            log.exception('reduce_data: %s', e)
+        # ruff: ignore[BLE001]
+        except Exception:
+            log.exception(f'Media.reduce_data: {self.pk}')
         else:
-            from common.logger import log
             # log the results of filtering / compacting on metadata size
             new_mdl = len(compact_json)
             if old_mdl > new_mdl:
@@ -720,6 +725,7 @@ def loaded_metadata(self):
                 pass
             setattr(self, '_cached_metadata_dict', data)
             return data
+        # ruff: ignore[BLE001]
         except Exception:
             return {}
 
@@ -742,7 +748,6 @@ def ts_to_dt(self, /, timestamp):
             timestamp_float = float(timestamp)
         except (TypeError, ValueError,) as e:
             log.warn(f'Could not compute published from timestamp for: {self.source} / {self} with "{e}"')
-            pass
         else:
             return self.posix_epoch + timedelta(seconds=timestamp_float)
         return None
@@ -775,14 +780,18 @@ def name(self):
 
     @property
     def upload_date(self):
+        ts = self.get_metadata_first_value('timestamp')
+        dt = self.ts_to_dt(ts) if ts else None
+        if dt and dt > self.posix_epoch:
+            return dt
+
         upload_date_str = self.get_metadata_first_value('upload_date')
         if not upload_date_str:
             return None
         try:
-            return datetime.strptime(upload_date_str, '%Y%m%d')
+            return datetime.strptime(upload_date_str, '%Y%m%d').replace(tzinfo=tz.utc)
         except (AttributeError, ValueError) as e:
             log.debug(f'Media.upload_date: {self.source} / {self}: strptime: {e}')
-            pass
         return None
 
     @property
@@ -841,7 +850,22 @@ def filename(self):
         media_format = str(self.source.media_format)
         media_details = self.format_dict
         result = media_format.format(**media_details)
-        return '.' + result if '/' == result[0] else result
+        result = '.' + result if '/' == result[0] else result
+        # Filesystems limit each path component to 255 bytes (not
+        # characters), and multi-byte titles can blow past that with far
+        # fewer characters — downloads then fail with:
+        #   [Errno 36] File name too long
+        # (issue #522). Only the final component (the name) is shortened;
+        # any directories in the format string are preserved. The budget
+        # leaves headroom for suffixes appended during download
+        # (`.fNNN.ext.part-FragNNN.part` and thumbnail/subtitle siblings).
+        path = Path(result)
+        truncated = truncate_filename(path.name)
+        if truncated != path.name:
+            log.warning(f'Media filename exceeded the filesystem byte limit '
+                        f'and was shortened: {self!r}')
+            return str(path.with_name(truncated))
+        return result
 
     @property
     def directory_path(self):
@@ -1022,10 +1046,11 @@ def get_download_state(self, task=None):
         if self.downloaded:
             return Val(MediaState.DOWNLOADED)
         if task:
+            # Avoid the circular import `ImportError` from using this at the top of the file.
+            from ..tasks import get_media_download_task
             def running(arg_task, /):
                 if hasattr(arg_task, 'locked_by_pid_running'):
                     return arg_task.locked_by_pid_running()
-                from ..tasks import get_media_download_task
                 return get_media_download_task(str(self.pk))
             if running(task):
                 return Val(MediaState.DOWNLOADING)
@@ -1063,6 +1088,7 @@ def index_metadata(self):
         '''
         indexer = self.INDEXERS.get(self.source.source_type, None)
         if not callable(indexer):
+            # ruff: ignore[TRY002,TRY004]
             raise Exception(f'Media with source type f"{self.source.source_type}" '
                             f'has no indexer')
         response = indexer(self.url)
diff --git a/tubesync/sync/tests/test_filepath.py b/tubesync/sync/tests/test_filepath.py
index a843e31fd..ed841b9b7 100644
--- a/tubesync/sync/tests/test_filepath.py
+++ b/tubesync/sync/tests/test_filepath.py
@@ -1,8 +1,10 @@
+import json
 import logging
 from pathlib import Path
 from django.conf import settings
 from django.test import TestCase
 from django.utils import timezone
+from common.utils import truncate_filename
 from sync.models import Source, Media
 from sync.choices import (
     Val, Fallback, SourceResolution,
@@ -158,6 +160,77 @@ def test_media_filename(self):
                          ('no-fancy-stuff-title_test_720p-720x1280-opus'
                           '-vp9-30fps-hdr.mkv'))
 
+    def test_media_filename_truncates_to_filesystem_byte_limit(self):
+        # Filesystems limit each name component to 255 bytes (issue #522).
+        # Multi-byte titles reach that with far fewer characters, and the
+        # download then fails with '[Errno 36] File name too long'.
+        long_metadata = json.loads(metadata)
+        long_metadata['title'] = '耳' * 120  # 3 bytes per char = 360 bytes
+        long_title_media = Media.objects.create(
+            key='longkey',
+            source=self.source,
+            metadata=json.dumps(long_metadata),
+        )
+        self.source.media_format = '{yyyy}/{title_full}_{key}.{ext}'
+        filename = long_title_media.filename
+        directory, _, name = filename.rpartition('/')
+        # Directories from the format string survive untouched
+        self.assertEqual('2017', directory)
+        # The name component fits in the byte budget...
+        self.assertLessEqual(len(name.encode('utf-8')), 216)
+        # ... keeps its extension and key suffix material intact ...
+        self.assertTrue(name.endswith('_longkey.mkv'))
+        # ... and was not cut mid multi-byte character (encodes cleanly)
+        name.encode('utf-8').decode('utf-8')
+
+    def test_media_filename_unchanged_when_within_limit(self):
+        self.source.media_format = '{yyyy}/{key}.{ext}'
+        self.assertEqual(self.media.filename, '2017/mediakey.mkv')
+
+    def test_truncate_filename_bytes_encoding_edge_cases(self):
+        # Bytes known to cause encoding/decoding trouble must never produce
+        # an invalid or over-budget name: the cut points land inside
+        # multi-byte sequences on purpose here.
+
+        cases = [
+            # 4-byte astral plane (emoji): cut lands mid-sequence
+            '🍣' * 100 + '_key.mkv',
+            # combining characters (é as e + U+0301)
+            ('e\u0301' * 150) + '_key.mkv',
+            # zero-width joiner sequences (family emoji)
+            ('👨\u200d👩\u200d👧\u200d👦' * 30) + '_key.mkv',
+            # mixed 1-byte/3-byte at every boundary parity
+            ('a耳' * 120) + '_key.mkv',
+            # right-to-left text
+            ('שלום' * 60) + '_key.mkv',
+            # no extension at all
+            '⽕' * 200,
+            # dotfile-style name (suffix is empty for PurePosixPath)
+            '.' + ('h' * 300),
+            # very long "extension" exceeding the whole budget
+            'name.' + ('x' * 300),
+        ]
+        for original in cases:
+            with self.subTest(original=original[:24]):
+                result = truncate_filename(original, max_bytes=208)
+                # fits the byte budget
+                self.assertLessEqual(len(result.encode('utf-8')), 208)
+                # still valid UTF-8 round-trip (no partial sequences kept)
+                self.assertEqual(
+                    result,
+                    result.encode('utf-8').decode('utf-8'),
+                )
+                # never empty
+                self.assertTrue(result)
+
+    def test_truncate_filename_bytes_rejects_non_str(self):
+
+        for bad in (None, 42, b'bytes.mkv', Path('p.mkv')):
+            # ruff: ignore[SIM117]
+            with self.subTest(bad=bad):
+                with self.assertRaises(TypeError):
+                    truncate_filename(bad)
+
     def test_directory_prefix(self):
         # Confirm the setting exists and is valid
         self.assertTrue(hasattr(settings, 'SOURCE_DOWNLOAD_DIRECTORY_PREFIX'))