diff --git a/app/features/streaming/library/segments.py b/app/features/streaming/library/segments.py
index 73c445d1..bee0d047 100644
--- a/app/features/streaming/library/segments.py
+++ b/app/features/streaming/library/segments.py
@@ -171,10 +171,9 @@ class Segments:
         stderr_task: asyncio.Task[None] = asyncio.create_task(_drain_stderr())
 
         LOG.debug(
-            "Streaming '%s' segment '%s'. ffmpeg: %s",
-            file,
+            "Streaming segment %s for '%s'.",
             self.index,
-            " ".join(args),
+            file,
             extra={"file": str(file), "segment_index": self.index, "ffmpeg_args": args},
         )
 
@@ -197,7 +196,10 @@ class Segments:
             try:
                 await asyncio.wait_for(proc.wait(), timeout=5)
             except TimeoutError:
-                LOG.warning("ffmpeg process did not terminate in time. Killing it.")
+                LOG.warning(
+                    "Segment stream for '%s' did not stop ffmpeg in time after the client disconnected; killing it.",
+                    file,
+                )
                 proc.kill()
             raise
         except ConnectionResetError:
@@ -210,7 +212,10 @@ class Segments:
                 try:
                     rc: int = await asyncio.wait_for(proc.wait(), timeout=5)
                 except TimeoutError:
-                    LOG.warning("ffmpeg process did not terminate in time after disconnect. Killing it.")
+                    LOG.warning(
+                        "Segment stream for '%s' did not stop ffmpeg in time after the client disconnected; killing it.",
+                        file,
+                    )
                     proc.kill()
                     try:
                         rc = await asyncio.wait_for(proc.wait(), timeout=5)
@@ -221,7 +226,7 @@ class Segments:
                 try:
                     rc = await asyncio.wait_for(proc.wait(), timeout=30)
                 except TimeoutError:
-                    LOG.warning("ffmpeg process wait timed out. Killing it.")
+                    LOG.warning("Segment stream for '%s' did not stop ffmpeg in time; killing the process.", file)
                     proc.kill()
                     try:
                         rc = await asyncio.wait_for(proc.wait(), timeout=5)
@@ -266,8 +271,10 @@ class Segments:
                 if 0 != rc:
                     err: str = stderr_text[:500] if stderr_text else "no error output"
                     LOG.warning(
-                        "Hardware encoder failed (rc=%s): %s. Trying fallbacks.",
-                        rc,
+                        "Retrying segment %s for '%s' because hardware encoder '%s' failed: %s.",
+                        self.index,
+                        file,
+                        s_codec,
                         err,
                         extra={"ffmpeg_args": ffmpeg_args, "returncode": rc, "stderr": err, "codec": s_codec},
                     )
diff --git a/app/features/streaming/library/thumbnail.py b/app/features/streaming/library/thumbnail.py
index dd432c06..31b40a31 100644
--- a/app/features/streaming/library/thumbnail.py
+++ b/app/features/streaming/library/thumbnail.py
@@ -35,7 +35,7 @@ def _get_semaphore() -> asyncio.Semaphore:
     if _SEM is None or _SEM_LIMIT != limit:
         _SEM = asyncio.Semaphore(limit)
         _SEM_LIMIT = limit
-        LOG.info("Thumbnail generation concurrency limit: %s", limit, extra={"limit": limit})
+        LOG.info("Configured thumbnail generation to run %s job(s) at a time.", limit, extra={"limit": limit})
 
     return _SEM
 
diff --git a/app/features/streaming/router.py b/app/features/streaming/router.py
index 3fc34637..7f33de5a 100644
--- a/app/features/streaming/router.py
+++ b/app/features/streaming/router.py
@@ -129,8 +129,10 @@ async def m3u8_create(request: Request, config: Config, app: web.Application) ->
             text = await cls.make_stream(file=realFile)
     except StreamingError as e:
         LOG.exception(
-            "Failed to create streaming playlist for '%s'.",
+            "Failed to create %s streaming playlist for '%s': %s.",
+            mode,
             file,
+            e,
             extra={"route": "streaming.playlist", "file_path": file, "mode": mode, "exception_type": type(e).__name__},
         )
         return web.json_response(data={"error": str(e)}, status=web.HTTPNotFound.status_code)
diff --git a/app/features/streaming/tests/test_segments.py b/app/features/streaming/tests/test_segments.py
index 33ec0e03..2c1d9eca 100644
--- a/app/features/streaming/tests/test_segments.py
+++ b/app/features/streaming/tests/test_segments.py
@@ -262,7 +262,7 @@ async def test_stream_gpu_fallback(
     assert len(resp.data) > 0
     # Ensure we logged the reason for GPU failure (message text may vary)
     assert any(
-        ("Hardware encoder failed" in r.message) or ("transcoding has failed" in r.message) for r in caplog.records
+        ("hardware encoder" in r.message.lower()) or ("transcoding has failed" in r.message) for r in caplog.records
     )
     assert any("nvenc failure" in r.message for r in caplog.records)
     # Verify second invocation switched codec to a safe fallback (software)
diff --git a/app/features/tasks/definitions/handlers/generic.py b/app/features/tasks/definitions/handlers/generic.py
index 51c276b7..40e924fe 100644
--- a/app/features/tasks/definitions/handlers/generic.py
+++ b/app/features/tasks/definitions/handlers/generic.py
@@ -561,7 +561,7 @@ class GenericTaskHandler(BaseHandler):
         container_selector = container.get("selector") or container.get("expression") or ""
         if not container_selector:
             LOG.error(
-                "Container missing selector/expression. Definition '%s'.",
+                "Task definition '%s' is missing an item container selector.",
                 definition.name,
                 extra={"definition": definition.name},
             )
@@ -771,7 +771,7 @@ class GenericTaskHandler(BaseHandler):
             return values
 
         if "jsonpath" == rule.type:
-            LOG.error("Extraction type 'jsonpath' is only valid for JSON responses.")
+            LOG.error("Field '%s' uses 'jsonpath' on a non-JSON response.", field, extra={"field": field})
             return values
 
         selection: SelectorList[Selector] = (
diff --git a/app/features/tasks/definitions/service.py b/app/features/tasks/definitions/service.py
index a5ae4ef9..dcc5a17c 100644
--- a/app/features/tasks/definitions/service.py
+++ b/app/features/tasks/definitions/service.py
@@ -158,7 +158,9 @@ class TaskHandle:
 
                 if result is None:
                     LOG.error(
-                        "Task handler returned no result.",
+                        "Handler '%s' returned no result for task '%s'.",
+                        handler.__name__,
+                        task.name,
                         extra={"task_id": task.id, "task_name": task.name, "handler_name": handler.__name__},
                     )
 
@@ -166,7 +168,7 @@ class TaskHandle:
 
         if len(tasks) > 0:
             LOG.info(
-                "Task handler summary: handled %s, unhandled %s, disabled %s, failed %s.",
+                "Task dispatch finished: %s handled, %s unhandled, %s disabled, %s failed.",
                 len(s["h"]),
                 len(s["u"]),
                 len(s["d"]),
@@ -296,14 +298,20 @@ class TaskHandle:
                 msg = f"{msg} {extraction.error}"
 
             LOG.error(
-                "Task handler failed to extract items.",
+                "Handler '%s' failed to extract items for task '%s' because %s.",
+                handler.__name__,
+                task.name,
+                msg,
                 extra={"task_id": task.id, "task_name": task.name, "handler_name": handler.__name__, "error": msg},
             )
             return extraction
 
         if not isinstance(extraction, TaskResult):
             LOG.error(
-                "Task handler returned unexpected result type.",
+                "Handler '%s' returned unexpected result type '%s' for task '%s'.",
+                handler.__name__,
+                type(extraction).__name__,
+                task.name,
                 extra={
                     "task_id": task.id,
                     "task_name": task.name,
@@ -338,7 +346,10 @@ class TaskHandle:
         for item in raw_items:
             if not isinstance(item, TaskItem):
                 LOG.warning(
-                    "Task handler returned unexpected item type.",
+                    "Handler '%s' returned unexpected item type '%s' for task '%s'.",
+                    handler.__name__,
+                    type(item).__name__,
+                    task.name,
                     extra={
                         "task_id": task.id,
                         "task_name": task.name,
@@ -355,7 +366,10 @@ class TaskHandle:
             archive_id: str | None = item.archive_id
             if not archive_id:
                 LOG.warning(
-                    "Task handler item is missing an archive ID.",
+                    "Handler '%s' skipped '%s' for task '%s' because it has no archive ID.",
+                    handler.__name__,
+                    url,
+                    task.name,
                     extra={"task_id": task.id, "task_name": task.name, "handler_name": handler.__name__, "url": url},
                 )
                 continue
@@ -386,7 +400,10 @@ class TaskHandle:
         if not filtered:
             if raw_items:
                 LOG.debug(
-                    "Task handler produced items, but none were queued after filtering.",
+                    "Handler '%s' found %s item(s) for task '%s', but none were queued.",
+                    handler.__name__,
+                    len(raw_items),
+                    task.name,
                     extra={
                         "task_id": task.id,
                         "task_name": task.name,
@@ -397,7 +414,10 @@ class TaskHandle:
             return TaskResult(items=[], metadata=metadata)
 
         LOG.info(
-            "Task handler found new items.",
+            "Handler '%s' found %s new item(s) for task '%s'.",
+            handler.__name__,
+            len(filtered),
+            task.name,
             extra={
                 "task_id": task.id,
                 "task_name": task.name,
@@ -548,7 +568,10 @@ class TaskHandle:
 
         if not isinstance(extraction, TaskResult):
             LOG.error(
-                "Task handler returned unexpected result type during inspection.",
+                "Handler '%s' returned unexpected result type '%s' while inspecting '%s'.",
+                handler_cls.__name__,
+                type(extraction).__name__,
+                url,
                 extra={"handler_name": handler_cls.__name__, "url": url, "result_type": type(extraction).__name__},
             )
             extraction = TaskResult()
diff --git a/app/features/tasks/router.py b/app/features/tasks/router.py
index aa601e23..9728ae0e 100644
--- a/app/features/tasks/router.py
+++ b/app/features/tasks/router.py
@@ -144,7 +144,12 @@ async def _get_info(url: str, preset: str) -> tuple[str | None, str | None]:
         LOG.debug("Timeout while inferring name from '%s'.", url, extra={"url": url, "preset": preset})
         return (None, None)
     except Exception as e:
-        LOG.debug("Failed to infer task name from URL.", extra={"url": url, "preset": preset, "error": str(e)})
+        LOG.debug(
+            "Failed to infer a task name from '%s' because %s.",
+            url,
+            e,
+            extra={"url": url, "preset": preset, "error": str(e)},
+        )
         return (None, None)
 
 
@@ -301,7 +306,6 @@ async def tasks_add(
                 "Failed to create task from request item %s.",
                 idx,
                 extra={"index": idx, "error": str(exc), "exception_type": type(exc).__name__},
-                exc_info=True,
             )
             continue
 
@@ -650,7 +654,8 @@ async def task_metadata(request: Request, repo: TasksRepository, config: Config,
                         save_path.mkdir(parents=True, exist_ok=True)
             except Exception as e:
                 LOG.warning(
-                    "Failed to resolve task metadata path from output template.",
+                    "Failed to resolve the metadata output path for task '%s'.",
+                    task.name,
                     extra={"task_id": task.id, "task_name": task.name, "error": str(e)},
                     exc_info=True,
                 )
@@ -734,7 +739,9 @@ async def task_metadata(request: Request, repo: TasksRepository, config: Config,
                 try:
                     url = thumbnails.get(key)
                     LOG.info(
-                        "Fetching task metadata thumbnail.",
+                        "Fetching '%s' thumbnail for task '%s'.",
+                        key,
+                        task.name,
                         extra={"task_id": task.id, "task_name": task.name, "thumbnail": key, "url": url},
                     )
                     if not url:
@@ -742,9 +749,12 @@ async def task_metadata(request: Request, repo: TasksRepository, config: Config,
 
                     try:
                         await asyncio.to_thread(validate_url, url, config.allow_internal_urls)
-                    except ValueError:
+                    except ValueError as exc:
                         LOG.warning(
-                            "Invalid task metadata thumbnail URL.",
+                            "Task '%s' has an invalid '%s' thumbnail URL because %s.",
+                            task.name,
+                            key,
+                            exc,
                             extra={"task_id": task.id, "task_name": task.name, "thumbnail": key, "url": url},
                         )
                         continue
@@ -761,7 +771,9 @@ async def task_metadata(request: Request, repo: TasksRepository, config: Config,
                     thumbnails[key] = str(img_file.relative_to(config.download_path))
                 except Exception as e:
                     LOG.warning(
-                        "Failed to fetch task metadata thumbnail.",
+                        "Failed to fetch '%s' thumbnail for task '%s'.",
+                        key,
+                        task.name,
                         extra={
                             "task_id": task.id,
                             "task_name": task.name,
@@ -774,7 +786,8 @@ async def task_metadata(request: Request, repo: TasksRepository, config: Config,
                     continue
         except Exception as e:
             LOG.warning(
-                "Failed to fetch task metadata thumbnails.",
+                "Failed to fetch metadata thumbnails for task '%s'.",
+                task.name,
                 extra={"task_id": task.id, "task_name": task.name, "error": str(e)},
                 exc_info=True,
             )
diff --git a/app/features/ytdlp/router.py b/app/features/ytdlp/router.py
index 7a3707b0..61f0bfae 100644
--- a/app/features/ytdlp/router.py
+++ b/app/features/ytdlp/router.py
@@ -38,8 +38,9 @@ def _get_preset_archive(preset: str) -> str | None:
         opts: dict = YTDLPOpts.get_instance().preset(preset).get_all()
     except Exception as e:
         LOG.exception(
-            "Failed to build yt-dlp options for preset '%s'.",
+            "Failed to build yt-dlp options for preset '%s': %s.",
             preset,
+            e,
             extra={"preset": preset, "exception_type": type(e).__name__},
         )
         return None
@@ -130,9 +131,10 @@ async def archiver_get(request: Request) -> Response:
         )
     except Exception as e:
         LOG.exception(
-            "Failed to read archive file '%s' for preset '%s'.",
+            "Failed to read archive file '%s' for preset '%s': %s.",
             archive_file,
             preset,
+            e,
             extra={
                 "route": "api/archiver/",
                 "action": "read_archive",
@@ -187,10 +189,11 @@ async def archiver_add(request: Request) -> Response:
         )
     except Exception as e:
         LOG.exception(
-            "Failed to add %s item(s) to archive file '%s' for preset '%s'.",
+            "Failed to add %s item(s) to archive file '%s' for preset '%s': %s.",
             len(items),
             archive_file,
             preset,
+            e,
             extra={
                 "route": "api/archiver/",
                 "action": "add_archive_items",
@@ -244,10 +247,11 @@ async def archiver_delete(request: Request) -> Response:
         )
     except Exception as e:
         LOG.exception(
-            "Failed to delete %s item(s) from archive file '%s' for preset '%s'.",
+            "Failed to delete %s item(s) from archive file '%s' for preset '%s': %s.",
             len(items),
             archive_file,
             preset,
+            e,
             extra={
                 "route": "api/archiver/",
                 "action": "delete_archive_items",
@@ -448,8 +452,9 @@ async def get_info(request: Request, cache: Cache, config: Config) -> Response:
         return web.json_response(body=json.dumps(data, indent=4, default=str), status=web.HTTPOk.status_code)
     except Exception as e:
         LOG.exception(
-            "Failed to get video info for '%s'.",
+            "Failed to get video info for '%s': %s.",
             url,
+            e,
             extra={
                 "route": "api/yt-dlp/url/info/",
                 "action": "get_video_info",
@@ -547,8 +552,9 @@ async def make_command(request: Request, config: Config, encoder: Encoder) -> Re
         command, info = YTDLPCli(item=it, config=config).build()
     except Exception as e:
         LOG.exception(
-            "Failed to build yt-dlp command for '%s'.",
+            "Failed to build yt-dlp command for '%s': %s.",
             it.url,
+            e,
             extra={
                 "route": "api/yt-dlp/command/",
                 "action": "build_command",
diff --git a/app/features/ytdlp/tests/test_ytdlp_opts.py b/app/features/ytdlp/tests/test_ytdlp_opts.py
index 7b728b2d..a9ed5f62 100644
--- a/app/features/ytdlp/tests/test_ytdlp_opts.py
+++ b/app/features/ytdlp/tests/test_ytdlp_opts.py
@@ -442,7 +442,7 @@ class TestYTDLPOpts:
             opts = YTDLPOpts()
             opts.get_all(keep=True)
 
-            mock_log.debug.assert_called_once_with("Final yt-dlp options", extra={"ytdlp_options": test_data})
+            mock_log.debug.assert_called_once_with("Prepared final yt-dlp options.", extra={"ytdlp_options": test_data})
 
     def test_cookie_loading_error_handling(self):
         """Test error handling when cookie loading fails."""
diff --git a/app/features/ytdlp/ytdlp_opts.py b/app/features/ytdlp/ytdlp_opts.py
index 5f4d094e..d0d7e2b4 100644
--- a/app/features/ytdlp/ytdlp_opts.py
+++ b/app/features/ytdlp/ytdlp_opts.py
@@ -336,8 +336,9 @@ class YTDLPOpts:
                     self._preset_opts["cookiefile"] = str(file)
             except ValueError as e:
                 LOG.exception(
-                    "Failed to load cookies for preset '%s'.",
+                    "Failed to load cookies for preset '%s': %s.",
                     preset.name,
+                    e,
                     extra={"preset": preset.name, "has_cookies": True, "exception_type": type(e).__name__},
                 )
 
@@ -407,7 +408,7 @@ class YTDLPOpts:
                 data["format"] = data["format"][1:]
 
         if self._config.debug:
-            LOG.debug("Final yt-dlp options", extra={"ytdlp_options": data})
+            LOG.debug("Prepared final yt-dlp options.", extra={"ytdlp_options": data})
 
         return data
 
diff --git a/app/library/BackgroundWorker.py b/app/library/BackgroundWorker.py
index b5770b13..a66974f2 100644
--- a/app/library/BackgroundWorker.py
+++ b/app/library/BackgroundWorker.py
@@ -39,14 +39,14 @@ class BackgroundWorker(metaclass=Singleton):
         Services.get_instance().add("background_worker", self)
         app.on_shutdown.append(self.on_shutdown)
 
-        LOG.debug("Starting background worker thread.")
+        LOG.debug("Started background worker thread.")
         self.thread = threading.Thread(target=self._run, daemon=True)
         self.thread.start()
 
     async def on_shutdown(self, _: web.Application):
         self.running = False
         try:
-            LOG.debug("Shutting down background worker thread...")
+            LOG.debug("Stopping background worker thread.")
             self.queue.put((CloseThread, (), {}))
             self.thread.join(timeout=5)
             LOG.debug("Background worker thread has been shut down.")
@@ -99,7 +99,7 @@ class BackgroundWorker(metaclass=Singleton):
             loop.call_soon_threadsafe(loop.stop)
             loop_thread.join(timeout=5)
             loop.close()
-            LOG.debug("Event loop has been stopped and closed.")
+            LOG.debug("Stopped background worker event loop.")
         except Exception as e:
             LOG.exception(
                 "Failed to stop background worker event loop.",
diff --git a/app/library/Events.py b/app/library/Events.py
index b1ea9fc6..d8c35819 100644
--- a/app/library/Events.py
+++ b/app/library/Events.py
@@ -327,7 +327,7 @@ class EventBus(metaclass=Singleton):
 
         if self.debug or event not in Events.only_debug():
             LOG.debug(
-                "Emitting '%s' event to %s listener(s).",
+                "Delivering '%s' event to %s listener(s).",
                 ev.event,
                 len(self._listeners[event]),
                 extra={
diff --git a/app/library/HttpSocket.py b/app/library/HttpSocket.py
index 6b419f46..eca2c6d2 100644
--- a/app/library/HttpSocket.py
+++ b/app/library/HttpSocket.py
@@ -145,7 +145,10 @@ class HttpSocket:
         for route in socket_routes.values():
             if self.config.debug:
                 LOG.debug(
-                    f"Add ({route.name}) {route.method.value if isinstance(route.method, RouteType) else route.method}: {route.path}."
+                    "Registered socket route '%s' for %s %s.",
+                    route.name,
+                    route.method.value if isinstance(route.method, RouteType) else route.method,
+                    route.path,
                 )
 
         async def handle_message(sid: str, message: str) -> None:
@@ -221,6 +224,6 @@ class HttpSocket:
             return ws
 
         if self.config.debug:
-            LOG.debug("Add (ws) GET: %s.", ws_path, extra={"method": "GET", "path": ws_path})
+            LOG.debug("Registered WebSocket endpoint at '%s'.", ws_path, extra={"method": "GET", "path": ws_path})
 
         app.router.add_get(ws_path, ws_handler, name="ws")
diff --git a/app/library/PackageInstaller.py b/app/library/PackageInstaller.py
index 9b796015..a643a50a 100644
--- a/app/library/PackageInstaller.py
+++ b/app/library/PackageInstaller.py
@@ -181,7 +181,7 @@ class PackageInstaller:
         if not pkgs.has_packages() or not self.user_site:
             return
 
-        LOG.info("Checking user pip packages: %s", ", ".join(pkgs.packages), extra={"packages": pkgs.packages})
+        LOG.info("Checking configured user pip packages.", extra={"packages": pkgs.packages})
         for package in pkgs.packages:
             try:
                 self.action(package, upgrade=pkgs.allow_upgrade())
diff --git a/app/library/TerminalSessionManager.py b/app/library/TerminalSessionManager.py
index 1a6b8c00..ac064cca 100644
--- a/app/library/TerminalSessionManager.py
+++ b/app/library/TerminalSessionManager.py
@@ -296,7 +296,7 @@ class TerminalSessionManager(metaclass=Singleton):
         master_fd: int | None = None
 
         try:
-            LOG.info("Cli command from client. '%s'", command)
+            LOG.info("Starting terminal session '%s' command.", session_id, extra={"session_id": session_id})
             args = ["yt-dlp", *shlex.split(command, posix=os.name != "nt")]
             env_vars = self._build_env()
 
@@ -377,7 +377,7 @@ class TerminalSessionManager(metaclass=Singleton):
                     try:
                         return_code = await asyncio.wait_for(proc.wait(), timeout=self._shutdown_timeout)
                     except TimeoutError:
-                        LOG.warning("Terminal session '%s' process did not exit cleanly.", session_id)
+                        LOG.warning("Terminal session '%s' did not exit after repeated shutdown attempts.", session_id)
 
             if proc is not None:
                 proc_returncode = getattr(proc, "returncode", None)
diff --git a/app/library/UpdateChecker.py b/app/library/UpdateChecker.py
index be857359..76b29deb 100644
--- a/app/library/UpdateChecker.py
+++ b/app/library/UpdateChecker.py
@@ -146,7 +146,7 @@ class UpdateChecker(metaclass=Singleton):
     ) -> tuple[str, str | None]:
         try:
             LOG.info(
-                "Checking for %s updates...",
+                "Checking whether %s has an update available.",
                 name,
                 extra={"target_name": name, "api_url": api_url, "current_version": current_version},
             )
@@ -183,7 +183,7 @@ class UpdateChecker(metaclass=Singleton):
 
             if self._compare_versions(compare_current, compare_latest):
                 LOG.warning(
-                    "%s update available: %s -> %s",
+                    "%s has an update available: %s -> %s.",
                     name,
                     current_version,
                     latest_tag,
@@ -194,7 +194,7 @@ class UpdateChecker(metaclass=Singleton):
                 return result
 
             LOG.info(
-                "No %s updates available.",
+                "%s is already up to date.",
                 name,
                 extra={"target_name": name, "current_version": current_version},
             )
@@ -203,7 +203,7 @@ class UpdateChecker(metaclass=Singleton):
             return result
         except Exception as e:
             LOG.exception(
-                "Failed to check for %s updates.",
+                "Failed to check whether %s has an update available.",
                 name,
                 extra={
                     "target_name": name,
@@ -234,7 +234,7 @@ class UpdateChecker(metaclass=Singleton):
     async def _check_ytdlp_version(self) -> tuple[str, str | None]:
         current_version: str = self._config._ytdlp_version()
         if not current_version or "0.0.0" == current_version:
-            LOG.warning("Could not determine yt-dlp version, skipping yt-dlp update check.")
+            LOG.warning("Skipping the yt-dlp update check because the current version could not be determined.")
             return ("error", None)
 
         status, new_version = await self._check_github_version(
@@ -270,7 +270,7 @@ class UpdateChecker(metaclass=Singleton):
             return parse_version(latest) > parse_version(current)
         except Exception as e:
             LOG.warning(
-                "Error comparing versions '%s' vs '%s': %s",
+                "Failed to compare versions '%s' and '%s' because %s.",
                 current,
                 latest,
                 e,
diff --git a/app/library/config.py b/app/library/config.py
index e671be31..55499a7a 100644
--- a/app/library/config.py
+++ b/app/library/config.py
@@ -443,7 +443,7 @@ class Config(metaclass=Singleton):
                     extra={"host": "0.0.0.0", "port": self.debugpy_port},
                 )
             except ImportError:
-                LOG.exception("debugpy package not found; install it with 'uv sync'.")
+                LOG.error("debugpy package not found; install it with 'uv sync'.")
             except Exception as e:
                 LOG.exception(
                     "Failed to start debugpy server.",
@@ -458,7 +458,7 @@ class Config(metaclass=Singleton):
 
         if self.auth_password and self.auth_username:
             LOG.info(
-                "Authentication enabled with username '%s'.",
+                "Basic authentication is enabled for user '%s'.",
                 self.auth_username,
                 extra={"auth_username": self.auth_username},
             )
diff --git a/app/library/downloads/hooks.py b/app/library/downloads/hooks.py
index dd446230..3dae6d4d 100644
--- a/app/library/downloads/hooks.py
+++ b/app/library/downloads/hooks.py
@@ -34,7 +34,7 @@ class HookHandlers:
             try:
                 d_safe = create_debug_safe_dict(data)
                 self.logger.debug(
-                    "Received progress hook for download '%s'.",
+                    "Received a yt-dlp progress update for download '%s'.",
                     self.id,
                     extra={"download": {"download_id": self.id, "hook": "progress", "status": d_safe}},
                 )
@@ -73,7 +73,7 @@ class HookHandlers:
                 d_safe = create_debug_safe_dict(data)
                 d_safe["postprocessor"] = data.get("postprocessor")
                 self.logger.debug(
-                    "Received postprocessor hook for download '%s'.",
+                    "Received a yt-dlp post-processing update for download '%s'.",
                     self.id,
                     extra={"download": {"download_id": self.id, "hook": "postprocessor", "status": d_safe}},
                 )
diff --git a/app/library/downloads/monitors.py b/app/library/downloads/monitors.py
index c13736d5..c18da55f 100644
--- a/app/library/downloads/monitors.py
+++ b/app/library/downloads/monitors.py
@@ -290,8 +290,9 @@ async def delete_old_history(queue: "DownloadQueue") -> None:
 
     if titles:
         LOG.info(
-            "Automatically cleared %s old history item(s).",
+            "Automatically cleared %s old history item(s), including '%s'.",
             len(titles),
+            titles[0],
             extra={"deleted_count": len(titles), "titles": titles},
         )
 
diff --git a/app/library/downloads/pool_manager.py b/app/library/downloads/pool_manager.py
index a566c570..91cf215d 100644
--- a/app/library/downloads/pool_manager.py
+++ b/app/library/downloads/pool_manager.py
@@ -79,7 +79,7 @@ class PoolManager:
     async def shutdown(self) -> None:
         if self._active:
             LOG.info(
-                "Cancelling %s active download(s).",
+                "Cancelling active downloads (%s item(s)).",
                 len(self._active),
                 extra={"active_count": len(self._active), "download_ids": list(self._active)},
             )
@@ -91,7 +91,7 @@ class PoolManager:
 
         while True:
             while not self.queue.queue.has_downloads():
-                LOG.info("Waiting for item to download.")
+                LOG.info("Waiting for queued downloads.")
                 await self.event.wait()
                 self.event.clear()
                 adaptive_sleep = 0.2
@@ -165,9 +165,8 @@ class PoolManager:
         """
         filePath: str = calc_download_path(base_path=self.config.download_path, folder=entry.info.folder)
         LOG.info(
-            "Downloading '%s' from '%s' to '%s'.",
+            "Started download for '%s' to '%s'.",
             entry.info.title,
-            entry.info.url,
             filePath,
             extra={
                 "download": {
@@ -246,7 +245,11 @@ class PoolManager:
                 message=nMessage,
             )
         else:
-            LOG.warning("Completed download '%s' was not found in queue.", id, extra={"download_id": id})
+            LOG.warning(
+                "Completed download '%s' was not found in the queue.",
+                entry.info.title or id,
+                extra={"download_id": id, "title": entry.info.title},
+            )
 
         if self.event:
             self.event.set()
diff --git a/app/library/downloads/queue_manager.py b/app/library/downloads/queue_manager.py
index 90fa84ed..a085867c 100644
--- a/app/library/downloads/queue_manager.py
+++ b/app/library/downloads/queue_manager.py
@@ -196,7 +196,7 @@ class DownloadQueue(metaclass=Singleton):
             self.pool.pause()
             if not shutdown:
                 paused_at = datetime.now(tz=UTC).isoformat()
-                LOG.warning("Download queue paused at %s.", paused_at, extra={"paused_at": paused_at})
+                LOG.warning("Paused the download queue.", extra={"paused_at": paused_at})
             return True
 
         return False
@@ -212,7 +212,7 @@ class DownloadQueue(metaclass=Singleton):
         if self.pool.is_paused():
             self.pool.resume()
             resumed_at = datetime.now(tz=UTC).isoformat()
-            LOG.warning("Download queue resumed at %s.", resumed_at, extra={"resumed_at": resumed_at})
+            LOG.warning("Resumed the download queue.", extra={"resumed_at": resumed_at})
             return True
 
         return False
@@ -630,7 +630,7 @@ class DownloadQueue(metaclass=Singleton):
         if deleted_count > 5:
             summary += ", ..."
         LOG.info(
-            "Cleared %s history item(s). %s",
+            "Cleared %s history item(s), including %s.",
             deleted_count,
             summary,
             extra={"deleted_count": deleted_count, "removed_files": removed_files, "titles": deleted_titles[:5]},
diff --git a/app/library/downloads/status_tracker.py b/app/library/downloads/status_tracker.py
index 3514f470..5a29a77c 100644
--- a/app/library/downloads/status_tracker.py
+++ b/app/library/downloads/status_tracker.py
@@ -166,7 +166,7 @@ class StatusTracker:
 
         if self.debug:
             self.logger.debug(
-                "Received status update for '%s'.",
+                "Received a download status update for '%s'.",
                 self.info.title,
                 extra={
                     "download": {
@@ -302,7 +302,9 @@ class StatusTracker:
                 self.update_task.cancel()
         except Exception as e:
             self.logger.exception(
-                f"Failed to cancel progress update task for '{self.info.title}'. {e!s}",
+                "Failed to cancel the progress update task for '%s' because %s.",
+                self.info.title,
+                e,
                 extra={
                     "download": {
                         "download_id": self.id,
diff --git a/app/library/downloads/temp_manager.py b/app/library/downloads/temp_manager.py
index e38c4729..2e309385 100644
--- a/app/library/downloads/temp_manager.py
+++ b/app/library/downloads/temp_manager.py
@@ -136,10 +136,9 @@ class TempManager:
             )
         else:
             self.logger.info(
-                "Temp folder '%s' deletion for '%s' %s.",
+                "Deleted temp folder '%s' for '%s'." if status else "Failed to delete temp folder '%s' for '%s'.",
                 self.temp_path,
                 self.info.title,
-                "succeeded" if status else "failed",
                 extra={
                     "download": {
                         "download_id": self.info._id,
diff --git a/app/library/sqlite_store.py b/app/library/sqlite_store.py
index 8e54a783..fe0766af 100644
--- a/app/library/sqlite_store.py
+++ b/app/library/sqlite_store.py
@@ -627,13 +627,13 @@ class SqliteStore(metaclass=ThreadSafe):
         self._conn = await self._engine.connect()
 
         if version := await migrate.get_version(self._conn):
-            LOG.debug("DB version: '%s'.", version, extra={"db_version": version})
+            LOG.debug("Database schema version is '%s'.", version, extra={"db_version": version})
 
         await migrate.upgrade(self._conn, ROOT_PATH / "migrations")
         if not version:
             migrated_version = await migrate.get_version(self._conn)
             LOG.debug(
-                "DB version after initial migration: '%s'.",
+                "Database schema was initialized at version '%s'.",
                 migrated_version,
                 extra={"db_version": migrated_version},
             )
diff --git a/app/main.py b/app/main.py
index 3a36be01..0fb6836a 100644
--- a/app/main.py
+++ b/app/main.py
@@ -164,7 +164,9 @@ class Main:
                 },
             )
             LOG.info(
-                "Download path: %s", self._config.download_path, extra={"download_path": self._config.download_path}
+                "Using download path '%s'.",
+                self._config.download_path,
+                extra={"download_path": self._config.download_path},
             )
             if self._config.is_native:
                 LOG.info("Running in native mode.")
diff --git a/app/routes/api/browser.py b/app/routes/api/browser.py
index 6c21cef6..b9923ec1 100644
--- a/app/routes/api/browser.py
+++ b/app/routes/api/browser.py
@@ -115,8 +115,9 @@ async def get_file_info(request: Request, config: Config, encoder: Encoder, app:
         return web.json_response(data=response, status=web.HTTPOk.status_code, dumps=encoder.encode)
     except Exception as e:
         LOG.exception(
-            "Failed to load file info for '%s'.",
+            "Failed to load file info for '%s' because %s.",
             file,
+            e,
             extra={"route": "file_info", "file_path": file},
         )
         return web.json_response(data={"error": str(e)}, status=web.HTTPInternalServerError.status_code)
@@ -201,8 +202,9 @@ async def file_browser(request: Request, config: Config, encoder: Encoder) -> Re
         )
     except OSError as e:
         LOG.exception(
-            "Failed to browse file path '%s'.",
+            "Failed to browse file path '%s' because %s.",
             req_path,
+            e,
             extra={"route": "file_browser", "request_path": req_path},
         )
         return web.json_response(data={"error": str(e)}, status=web.HTTPInternalServerError.status_code)
@@ -236,8 +238,11 @@ async def path_actions(request: Request, config: Config, queue: DownloadQueue, n
             return web.json_response(
                 data={"error": "Invalid parameters expecting list of dicts."}, status=web.HTTPBadRequest.status_code
             )
-    except Exception:
-        LOG.exception("Failed to parse file browser actions request.", extra={"route": "browser.file.actions"})
+    except Exception as e:
+        LOG.debug(
+            "Ignoring invalid file browser actions JSON.",
+            extra={"route": "browser.file.actions", "error": str(e)},
+        )
         return web.json_response(data={"error": "Invalid JSON."}, status=web.HTTPBadRequest.status_code)
 
     # validate each action before performing any operations
@@ -338,9 +343,10 @@ async def path_actions(request: Request, config: Config, queue: DownloadQueue, n
                 continue
         except Exception as e:
             LOG.exception(
-                "Failed to resolve file browser action '%s' for path '%s'.",
+                "Failed to resolve file browser action '%s' for path '%s' because %s.",
                 action,
                 req_path,
+                e,
                 extra={"route": "browser.file.actions", "action": action, "request_path": req_path},
             )
             record(req_path, ok=False, error=str(e), action=action, extra={"item": params})
@@ -391,8 +397,9 @@ async def path_actions(request: Request, config: Config, queue: DownloadQueue, n
                 )
             except OSError as e:
                 LOG.exception(
-                    "Failed to create directory '%s'.",
+                    "Failed to create directory '%s' because %s.",
                     new_dir,
+                    e,
                     extra={
                         "route": "browser.file.actions",
                         "action": action,
@@ -438,8 +445,9 @@ async def path_actions(request: Request, config: Config, queue: DownloadQueue, n
                 )
             except OSError as e:
                 LOG.exception(
-                    "Failed to rename file browser path '%s'.",
+                    "Failed to rename file browser path '%s' because %s.",
                     path.relative_to(config.download_path),
+                    e,
                     extra={
                         "route": "browser.file.actions",
                         "action": action,
@@ -487,8 +495,9 @@ async def path_actions(request: Request, config: Config, queue: DownloadQueue, n
                 )
             except OSError as e:
                 LOG.exception(
-                    "Failed to delete file browser path '%s'.",
+                    "Failed to delete file browser path '%s' because %s.",
                     path.relative_to(config.download_path),
+                    e,
                     extra={
                         "route": "browser.file.actions",
                         "action": action,
@@ -566,8 +575,9 @@ async def path_actions(request: Request, config: Config, queue: DownloadQueue, n
                 )
             except OSError as e:
                 LOG.exception(
-                    "Failed to move file browser path '%s'.",
+                    "Failed to move file browser path '%s' because %s.",
                     path.relative_to(config.download_path),
+                    e,
                     extra={
                         "route": "browser.file.actions",
                         "action": action,
@@ -673,16 +683,14 @@ async def stream_zip_download(request: Request, config: Config, cache: Cache) ->
 
     try:
         LOG.info(
-            "Streaming zip download for token '%s' with %d file(s).",
-            token,
+            "Started streaming a ZIP download with %d file(s).",
             len(files),
             extra={"route": "browser.download.stream", "token": token, "file_count": len(files)},
         )
         for chunk in zs:
             if request.transport is None or request.transport.is_closing():
                 LOG.info(
-                    "Client disconnected, aborting zip download for token '%s'.",
-                    token,
+                    "Stopped streaming the ZIP download because the client disconnected.",
                     extra={"route": "browser.download.stream", "token": token},
                 )
                 break
@@ -690,14 +698,12 @@ async def stream_zip_download(request: Request, config: Config, cache: Cache) ->
         await response.write_eof()
     except asyncio.CancelledError:
         LOG.info(
-            "Download cancelled by client for token '%s'.",
-            token,
+            "Stopped streaming the ZIP download because the client cancelled it.",
             extra={"route": "browser.download.stream", "token": token},
         )
     except Exception as e:
         LOG.exception(
-            "Streaming zip download failed for token '%s'.",
-            token,
+            "Failed to stream the ZIP download.",
             extra={
                 "route": "browser.download.stream",
                 "token": token,
diff --git a/app/routes/api/history.py b/app/routes/api/history.py
index 864e9b74..5ce775c3 100644
--- a/app/routes/api/history.py
+++ b/app/routes/api/history.py
@@ -476,10 +476,9 @@ async def item_update(request: Request, queue: DownloadQueue, encoder: Encoder,
         updated = True
         setattr(item.info, k, v)
         LOG.debug(
-            "Updated '%s' to '%s' for '%s'.",
-            k,
-            v,
+            "Updated history item '%s' field '%s'.",
             item.info.id,
+            k,
             extra={"route": "history.item_update", "item_id": item.info.id, "field": k, "value": v},
         )
 
diff --git a/app/routes/api/logs.py b/app/routes/api/logs.py
index f4ac708a..969f8a53 100644
--- a/app/routes/api/logs.py
+++ b/app/routes/api/logs.py
@@ -215,7 +215,6 @@ async def stream_logs(request: Request, config: Config, encoder: Encoder) -> Res
     )
 
     try:
-        LOG.debug("Log streaming connected.")
         while not log_task.done():
             await asyncio.sleep(1.0)
             if request.transport is None or request.transport.is_closing():
@@ -225,7 +224,6 @@ async def stream_logs(request: Request, config: Config, encoder: Encoder) -> Res
     except asyncio.CancelledError:
         pass
     finally:
-        LOG.debug("Log streaming disconnected.")
         try:
             await response.write_eof()
         except ConnectionResetError: