diff --git a/unshackle/core/downloaders/aria2c.py b/unshackle/core/downloaders/aria2c.py
index bc43460..6f5b5d0 100644
--- a/unshackle/core/downloaders/aria2c.py
+++ b/unshackle/core/downloaders/aria2c.py
@@ -19,7 +19,7 @@ from unshackle.core import binaries
 from unshackle.core.config import config
 from unshackle.core.console import console
 from unshackle.core.constants import DOWNLOAD_CANCELLED
-from unshackle.core.utilities import get_extension, get_free_port
+from unshackle.core.utilities import get_debug_logger, get_extension, get_free_port
 
 
 def rpc(caller: Callable, secret: str, method: str, params: Optional[list[Any]] = None) -> Any:
@@ -58,6 +58,8 @@ def download(
     proxy: Optional[str] = None,
     max_workers: Optional[int] = None,
 ) -> Generator[dict[str, Any], None, None]:
+    debug_logger = get_debug_logger()
+
     if not urls:
         raise ValueError("urls must be provided and not empty")
     elif not isinstance(urls, (str, dict, list)):
@@ -91,6 +93,13 @@ def download(
         urls = [urls]
 
     if not binaries.Aria2:
+        if debug_logger:
+            debug_logger.log(
+                level="ERROR",
+                operation="downloader_aria2c_binary_missing",
+                message="Aria2c executable not found in PATH or local binaries directory",
+                context={"searched_names": ["aria2c", "aria2"]},
+            )
         raise EnvironmentError("Aria2c executable not found...")
 
     if proxy and not proxy.lower().startswith("http://"):
@@ -180,6 +189,28 @@ def download(
             continue
         arguments.extend(["--header", f"{header}: {value}"])
 
+    if debug_logger:
+        first_url = urls[0] if isinstance(urls[0], str) else urls[0].get("url", "")
+        url_display = first_url[:200] + "..." if len(first_url) > 200 else first_url
+        debug_logger.log(
+            level="DEBUG",
+            operation="downloader_aria2c_start",
+            message="Starting Aria2c download",
+            context={
+                "binary_path": str(binaries.Aria2),
+                "url_count": len(urls),
+                "first_url": url_display,
+                "output_dir": str(output_dir),
+                "filename": filename,
+                "max_concurrent_downloads": max_concurrent_downloads,
+                "max_connection_per_server": max_connection_per_server,
+                "split": split,
+                "file_allocation": file_allocation,
+                "has_proxy": bool(proxy),
+                "rpc_port": rpc_port,
+            },
+        )
+
     yield dict(total=len(urls))
 
     try:
@@ -226,6 +257,20 @@ def download(
                         textwrap.wrap(error, width=console.width - 20, initial_indent="")
                     )
                     console.log(Text.from_ansi("\n[Aria2c]: " + error_pretty))
+                    if debug_logger:
+                        debug_logger.log(
+                            level="ERROR",
+                            operation="downloader_aria2c_download_error",
+                            message=f"Aria2c download failed: {dl['errorMessage']}",
+                            context={
+                                "gid": dl["gid"],
+                                "error_code": dl["errorCode"],
+                                "error_message": dl["errorMessage"],
+                                "used_uri": used_uri[:200] + "..." if len(used_uri) > 200 else used_uri,
+                                "completed_length": dl.get("completedLength"),
+                                "total_length": dl.get("totalLength"),
+                            },
+                        )
                     raise ValueError(error)
 
             if number_stopped == len(urls):
@@ -237,7 +282,31 @@ def download(
         p.wait()
 
         if p.returncode != 0:
+            if debug_logger:
+                debug_logger.log(
+                    level="ERROR",
+                    operation="downloader_aria2c_failed",
+                    message=f"Aria2c exited with code {p.returncode}",
+                    context={
+                        "returncode": p.returncode,
+                        "url_count": len(urls),
+                        "output_dir": str(output_dir),
+                    },
+                )
             raise subprocess.CalledProcessError(p.returncode, arguments)
+
+        if debug_logger:
+            debug_logger.log(
+                level="DEBUG",
+                operation="downloader_aria2c_complete",
+                message="Aria2c download completed successfully",
+                context={
+                    "url_count": len(urls),
+                    "output_dir": str(output_dir),
+                    "filename": filename,
+                },
+            )
+
     except ConnectionResetError:
         # interrupted while passing URI to download
         raise KeyboardInterrupt()
@@ -251,9 +320,20 @@ def download(
         DOWNLOAD_CANCELLED.set()  # skip pending track downloads
         yield dict(downloaded="[yellow]CANCELLED")
         raise
-    except Exception:
+    except Exception as e:
         DOWNLOAD_CANCELLED.set()  # skip pending track downloads
         yield dict(downloaded="[red]FAILED")
+        if debug_logger and not isinstance(e, (subprocess.CalledProcessError, ValueError)):
+            debug_logger.log(
+                level="ERROR",
+                operation="downloader_aria2c_exception",
+                message=f"Unexpected error during Aria2c download: {e}",
+                error=e,
+                context={
+                    "url_count": len(urls),
+                    "output_dir": str(output_dir),
+                },
+            )
         raise
     finally:
         rpc(caller=partial(rpc_session.post, url=rpc_uri), secret=rpc_secret, method="aria2.shutdown")
diff --git a/unshackle/core/downloaders/curl_impersonate.py b/unshackle/core/downloaders/curl_impersonate.py
index 52dab7a..d278e91 100644
--- a/unshackle/core/downloaders/curl_impersonate.py
+++ b/unshackle/core/downloaders/curl_impersonate.py
@@ -11,7 +11,7 @@ from rich import filesize
 
 from unshackle.core.config import config
 from unshackle.core.constants import DOWNLOAD_CANCELLED
-from unshackle.core.utilities import get_extension
+from unshackle.core.utilities import get_debug_logger, get_extension
 
 MAX_ATTEMPTS = 5
 RETRY_WAIT = 2
@@ -189,6 +189,8 @@ def curl_impersonate(
     if not isinstance(max_workers, (int, type(None))):
         raise TypeError(f"Expected max_workers to be {int}, not {type(max_workers)}")
 
+    debug_logger = get_debug_logger()
+
     if not isinstance(urls, list):
         urls = [urls]
 
@@ -209,6 +211,24 @@ def curl_impersonate(
     if proxy:
         session.proxies.update({"all": proxy})
 
+    if debug_logger:
+        first_url = urls[0].get("url", "") if urls else ""
+        url_display = first_url[:200] + "..." if len(first_url) > 200 else first_url
+        debug_logger.log(
+            level="DEBUG",
+            operation="downloader_curl_impersonate_start",
+            message="Starting curl_impersonate download",
+            context={
+                "url_count": len(urls),
+                "first_url": url_display,
+                "output_dir": str(output_dir),
+                "filename": filename,
+                "max_workers": max_workers,
+                "browser": BROWSER,
+                "has_proxy": bool(proxy),
+            },
+        )
+
     yield dict(total=len(urls))
 
     download_sizes = []
@@ -235,11 +255,23 @@ def curl_impersonate(
                 # tell dl that it was cancelled
                 # the pool is already shut down, so exiting loop is fine
                 raise
-            except Exception:
+            except Exception as e:
                 DOWNLOAD_CANCELLED.set()  # skip pending track downloads
                 yield dict(downloaded="[red]FAILING")
                 pool.shutdown(wait=True, cancel_futures=True)
                 yield dict(downloaded="[red]FAILED")
+                if debug_logger:
+                    debug_logger.log(
+                        level="ERROR",
+                        operation="downloader_curl_impersonate_failed",
+                        message=f"curl_impersonate download failed: {e}",
+                        error=e,
+                        context={
+                            "url_count": len(urls),
+                            "output_dir": str(output_dir),
+                            "browser": BROWSER,
+                        },
+                    )
                 # tell dl that it failed
                 # the pool is already shut down, so exiting loop is fine
                 raise
@@ -260,5 +292,17 @@ def curl_impersonate(
                     last_speed_refresh = now
                     download_sizes.clear()
 
+    if debug_logger:
+        debug_logger.log(
+            level="DEBUG",
+            operation="downloader_curl_impersonate_complete",
+            message="curl_impersonate download completed successfully",
+            context={
+                "url_count": len(urls),
+                "output_dir": str(output_dir),
+                "filename": filename,
+            },
+        )
+
 
 __all__ = ("curl_impersonate",)
diff --git a/unshackle/core/downloaders/n_m3u8dl_re.py b/unshackle/core/downloaders/n_m3u8dl_re.py
index 7472c59..815c697 100644
--- a/unshackle/core/downloaders/n_m3u8dl_re.py
+++ b/unshackle/core/downloaders/n_m3u8dl_re.py
@@ -13,6 +13,7 @@ from unshackle.core import binaries
 from unshackle.core.config import config
 from unshackle.core.console import console
 from unshackle.core.constants import DOWNLOAD_CANCELLED
+from unshackle.core.utilities import get_debug_logger
 
 PERCENT_RE = re.compile(r"(\d+\.\d+%)")
 SPEED_RE = re.compile(r"(\d+\.\d+(?:MB|KB)ps)")
@@ -176,7 +177,6 @@ def build_download_args(
         "--thread-count": thread_count,
         "--download-retry-count": retry_count,
         "--write-meta-json": False,
-        "--no-log": True,
     }
     if proxy:
         args["--custom-proxy"] = proxy
@@ -224,6 +224,8 @@ def download(
     content_keys: dict[str, Any] | None,
     skip_merge: bool | None = False,
 ) -> Generator[dict[str, Any], None, None]:
+    debug_logger = get_debug_logger()
+
     if not urls:
         raise ValueError("urls must be provided and not empty")
     if not isinstance(urls, (str, dict, list)):
@@ -275,7 +277,39 @@ def download(
         skip_merge=skip_merge,
         ad_keyword=ad_keyword,
     )
-    arguments.extend(get_track_selection_args(track))
+    selection_args = get_track_selection_args(track)
+    arguments.extend(selection_args)
+
+    log_file_path: Path | None = None
+    if debug_logger:
+        log_file_path = output_dir / f".n_m3u8dl_re_{filename}.log"
+        arguments.extend(["--log-file-path", str(log_file_path)])
+
+        track_url_display = track.url[:200] + "..." if len(track.url) > 200 else track.url
+        debug_logger.log(
+            level="DEBUG",
+            operation="downloader_n_m3u8dl_re_start",
+            message="Starting N_m3u8DL-RE download",
+            context={
+                "binary_path": str(binaries.N_m3u8DL_RE),
+                "track_id": getattr(track, "id", None),
+                "track_type": track.__class__.__name__,
+                "track_url": track_url_display,
+                "output_dir": str(output_dir),
+                "filename": filename,
+                "thread_count": thread_count,
+                "retry_count": retry_count,
+                "has_content_keys": bool(content_keys),
+                "content_key_count": len(content_keys) if content_keys else 0,
+                "has_proxy": bool(proxy),
+                "skip_merge": skip_merge,
+                "has_custom_args": bool(track.downloader_args),
+                "selection_args": selection_args,
+                "descriptor": track.descriptor.name if hasattr(track, "descriptor") else None,
+            },
+        )
+    else:
+        arguments.extend(["--no-log", "true"])
 
     yield {"total": 100}
     yield {"downloaded": "Parsing streams..."}
@@ -310,11 +344,45 @@ def download(
                     yield {"completed": progress} if progress < 100 else {"downloaded": "Merging"}
 
             process.wait()
+
         if process.returncode != 0:
+            if debug_logger and log_file_path:
+                log_contents = ""
+                if log_file_path.exists():
+                    try:
+                        log_contents = log_file_path.read_text(encoding="utf-8", errors="replace")
+                    except Exception:
+                        log_contents = "<failed to read log file>"
+
+                debug_logger.log(
+                    level="ERROR",
+                    operation="downloader_n_m3u8dl_re_failed",
+                    message=f"N_m3u8DL-RE exited with code {process.returncode}",
+                    context={
+                        "returncode": process.returncode,
+                        "track_id": getattr(track, "id", None),
+                        "track_type": track.__class__.__name__,
+                        "last_line": last_line,
+                        "log_file_contents": log_contents,
+                    },
+                )
             if error_match := ERROR_RE.search(last_line):
                 raise ValueError(f"[N_m3u8DL-RE]: {error_match.group(1)}")
             raise subprocess.CalledProcessError(process.returncode, arguments)
 
+        if debug_logger:
+            debug_logger.log(
+                level="DEBUG",
+                operation="downloader_n_m3u8dl_re_complete",
+                message="N_m3u8DL-RE download completed successfully",
+                context={
+                    "track_id": getattr(track, "id", None),
+                    "track_type": track.__class__.__name__,
+                    "output_dir": str(output_dir),
+                    "filename": filename,
+                },
+            )
+
     except ConnectionResetError:
         # interrupted while passing URI to download
         raise KeyboardInterrupt()
@@ -322,10 +390,35 @@ def download(
         DOWNLOAD_CANCELLED.set()  # skip pending track downloads
         yield {"downloaded": "[yellow]CANCELLED"}
         raise
-    except Exception:
+    except Exception as e:
         DOWNLOAD_CANCELLED.set()  # skip pending track downloads
         yield {"downloaded": "[red]FAILED"}
+        if debug_logger and log_file_path and not isinstance(e, (subprocess.CalledProcessError, ValueError)):
+            log_contents = ""
+            if log_file_path.exists():
+                try:
+                    log_contents = log_file_path.read_text(encoding="utf-8", errors="replace")
+                except Exception:
+                    log_contents = "<failed to read log file>"
+
+            debug_logger.log(
+                level="ERROR",
+                operation="downloader_n_m3u8dl_re_exception",
+                message=f"Unexpected error during N_m3u8DL-RE download: {e}",
+                error=e,
+                context={
+                    "track_id": getattr(track, "id", None),
+                    "track_type": track.__class__.__name__,
+                    "log_file_contents": log_contents,
+                },
+            )
         raise
+    finally:
+        if log_file_path and log_file_path.exists():
+            try:
+                log_file_path.unlink()
+            except Exception:
+                pass
 
 
 def n_m3u8dl_re(
diff --git a/unshackle/core/downloaders/requests.py b/unshackle/core/downloaders/requests.py
index 49c1759..06cab3d 100644
--- a/unshackle/core/downloaders/requests.py
+++ b/unshackle/core/downloaders/requests.py
@@ -12,7 +12,7 @@ from requests.adapters import HTTPAdapter
 from rich import filesize
 
 from unshackle.core.constants import DOWNLOAD_CANCELLED
-from unshackle.core.utilities import get_extension
+from unshackle.core.utilities import get_debug_logger, get_extension
 
 MAX_ATTEMPTS = 5
 RETRY_WAIT = 2
@@ -215,6 +215,8 @@ def requests(
     if not isinstance(max_workers, (int, type(None))):
         raise TypeError(f"Expected max_workers to be {int}, not {type(max_workers)}")
 
+    debug_logger = get_debug_logger()
+
     if not isinstance(urls, list):
         urls = [urls]
 
@@ -241,6 +243,23 @@ def requests(
     if proxy:
         session.proxies.update({"all": proxy})
 
+    if debug_logger:
+        first_url = urls[0].get("url", "") if urls else ""
+        url_display = first_url[:200] + "..." if len(first_url) > 200 else first_url
+        debug_logger.log(
+            level="DEBUG",
+            operation="downloader_requests_start",
+            message="Starting requests download",
+            context={
+                "url_count": len(urls),
+                "first_url": url_display,
+                "output_dir": str(output_dir),
+                "filename": filename,
+                "max_workers": max_workers,
+                "has_proxy": bool(proxy),
+            },
+        )
+
     yield dict(total=len(urls))
 
     try:
@@ -256,14 +275,37 @@ def requests(
                     # tell dl that it was cancelled
                     # the pool is already shut down, so exiting loop is fine
                     raise
-                except Exception:
+                except Exception as e:
                     DOWNLOAD_CANCELLED.set()  # skip pending track downloads
                     yield dict(downloaded="[red]FAILING")
                     pool.shutdown(wait=True, cancel_futures=True)
                     yield dict(downloaded="[red]FAILED")
+                    if debug_logger:
+                        debug_logger.log(
+                            level="ERROR",
+                            operation="downloader_requests_failed",
+                            message=f"Requests download failed: {e}",
+                            error=e,
+                            context={
+                                "url_count": len(urls),
+                                "output_dir": str(output_dir),
+                            },
+                        )
                     # tell dl that it failed
                     # the pool is already shut down, so exiting loop is fine
                     raise
+
+        if debug_logger:
+            debug_logger.log(
+                level="DEBUG",
+                operation="downloader_requests_complete",
+                message="Requests download completed successfully",
+                context={
+                    "url_count": len(urls),
+                    "output_dir": str(output_dir),
+                    "filename": filename,
+                },
+            )
     finally:
         DOWNLOAD_SIZES.clear()
 
diff --git a/unshackle/core/manifests/dash.py b/unshackle/core/manifests/dash.py
index 442ac96..68fdded 100644
--- a/unshackle/core/manifests/dash.py
+++ b/unshackle/core/manifests/dash.py
@@ -28,7 +28,7 @@ from unshackle.core.downloaders import requests as requests_downloader
 from unshackle.core.drm import DRM_T, PlayReady, Widevine
 from unshackle.core.events import events
 from unshackle.core.tracks import Audio, Subtitle, Tracks, Video
-from unshackle.core.utilities import is_close_match, try_ensure_utf8
+from unshackle.core.utilities import get_debug_logger, is_close_match, try_ensure_utf8
 from unshackle.core.utils.xml import load_xml
 
 
@@ -518,6 +518,24 @@ class DASH:
         if downloader.__name__ == "n_m3u8dl_re":
             downloader_args.update({"filename": track.id, "track": track})
 
+        debug_logger = get_debug_logger()
+        if debug_logger:
+            debug_logger.log(
+                level="DEBUG",
+                operation="manifest_dash_download_start",
+                message="Starting DASH manifest download",
+                context={
+                    "track_id": getattr(track, "id", None),
+                    "track_type": track.__class__.__name__,
+                    "total_segments": len(segments),
+                    "downloader": downloader.__name__,
+                    "has_drm": bool(track.drm),
+                    "drm_types": [drm.__class__.__name__ for drm in (track.drm or [])],
+                    "save_path": str(save_path),
+                    "has_init_data": bool(init_data),
+                },
+            )
+
         for status_update in downloader(**downloader_args):
             file_downloaded = status_update.get("file_downloaded")
             if file_downloaded:
diff --git a/unshackle/core/manifests/hls.py b/unshackle/core/manifests/hls.py
index 6f49c6a..fb0320b 100644
--- a/unshackle/core/manifests/hls.py
+++ b/unshackle/core/manifests/hls.py
@@ -32,7 +32,7 @@ from unshackle.core.downloaders import requests as requests_downloader
 from unshackle.core.drm import DRM_T, ClearKey, PlayReady, Widevine
 from unshackle.core.events import events
 from unshackle.core.tracks import Audio, Subtitle, Tracks, Video
-from unshackle.core.utilities import get_extension, is_close_match, try_ensure_utf8
+from unshackle.core.utilities import get_debug_logger, get_extension, is_close_match, try_ensure_utf8
 
 
 class HLS:
@@ -350,6 +350,24 @@ class HLS:
                 }
             )
 
+        debug_logger = get_debug_logger()
+        if debug_logger:
+            debug_logger.log(
+                level="DEBUG",
+                operation="manifest_hls_download_start",
+                message="Starting HLS manifest download",
+                context={
+                    "track_id": getattr(track, "id", None),
+                    "track_type": track.__class__.__name__,
+                    "total_segments": total_segments,
+                    "downloader": downloader.__name__,
+                    "has_drm": bool(session_drm),
+                    "drm_type": session_drm.__class__.__name__ if session_drm else None,
+                    "skip_merge": skip_merge,
+                    "save_path": str(save_path),
+                },
+            )
+
         for status_update in downloader(**downloader_args):
             file_downloaded = status_update.get("file_downloaded")
             if file_downloaded:
diff --git a/unshackle/core/manifests/ism.py b/unshackle/core/manifests/ism.py
index 346c9e6..8cb6a3b 100644
--- a/unshackle/core/manifests/ism.py
+++ b/unshackle/core/manifests/ism.py
@@ -21,7 +21,7 @@ from unshackle.core.constants import DOWNLOAD_CANCELLED, DOWNLOAD_LICENCE_ONLY,
 from unshackle.core.drm import DRM_T, PlayReady, Widevine
 from unshackle.core.events import events
 from unshackle.core.tracks import Audio, Subtitle, Track, Tracks, Video
-from unshackle.core.utilities import try_ensure_utf8
+from unshackle.core.utilities import get_debug_logger, try_ensure_utf8
 from unshackle.core.utils.xml import load_xml
 
 
@@ -283,6 +283,24 @@ class ISM:
                 }
             )
 
+        debug_logger = get_debug_logger()
+        if debug_logger:
+            debug_logger.log(
+                level="DEBUG",
+                operation="manifest_ism_download_start",
+                message="Starting ISM manifest download",
+                context={
+                    "track_id": getattr(track, "id", None),
+                    "track_type": track.__class__.__name__,
+                    "total_segments": len(segments),
+                    "downloader": downloader.__name__,
+                    "has_drm": bool(session_drm),
+                    "drm_type": session_drm.__class__.__name__ if session_drm else None,
+                    "skip_merge": skip_merge,
+                    "save_path": str(save_path),
+                },
+            )
+
         for status_update in downloader(**downloader_args):
             file_downloaded = status_update.get("file_downloaded")
             if file_downloaded:
diff --git a/unshackle/core/tracks/tracks.py b/unshackle/core/tracks/tracks.py
index eeacd47..fd9d78d 100644
--- a/unshackle/core/tracks/tracks.py
+++ b/unshackle/core/tracks/tracks.py
@@ -22,7 +22,7 @@ from unshackle.core.tracks.chapters import Chapter, Chapters
 from unshackle.core.tracks.subtitle import Subtitle
 from unshackle.core.tracks.track import Track
 from unshackle.core.tracks.video import Video
-from unshackle.core.utilities import is_close_match, sanitize_filename
+from unshackle.core.utilities import get_debug_logger, is_close_match, sanitize_filename
 from unshackle.core.utils.collections import as_list, flatten
 
 
@@ -507,6 +507,35 @@ class Tracks:
         if not output_path:
             raise ValueError("No tracks provided, at least one track must be provided.")
 
+        debug_logger = get_debug_logger()
+        if debug_logger:
+            debug_logger.log(
+                level="DEBUG",
+                operation="mux_start",
+                message="Starting mkvmerge muxing",
+                context={
+                    "title": title,
+                    "output_path": str(output_path),
+                    "video_count": len(self.videos),
+                    "audio_count": len(self.audio),
+                    "subtitle_count": len(self.subtitles),
+                    "attachment_count": len(self.attachments),
+                    "has_chapters": bool(self.chapters),
+                    "video_tracks": [
+                        {"id": v.id, "codec": getattr(v, "codec", None), "language": str(v.language)}
+                        for v in self.videos
+                    ],
+                    "audio_tracks": [
+                        {"id": a.id, "codec": getattr(a, "codec", None), "language": str(a.language)}
+                        for a in self.audio
+                    ],
+                    "subtitle_tracks": [
+                        {"id": s.id, "codec": getattr(s, "codec", None), "language": str(s.language)}
+                        for s in self.subtitles
+                    ],
+                },
+            )
+
         # let potential failures go to caller, caller should handle
         try:
             errors = []
@@ -516,7 +545,33 @@ class Tracks:
                     errors.append(line)
                 if "progress" in line:
                     progress(total=100, completed=int(line.strip()[14:-1]))
-            return output_path, p.wait(), errors
+
+            returncode = p.wait()
+
+            if debug_logger:
+                if returncode != 0 or errors:
+                    debug_logger.log(
+                        level="ERROR",
+                        operation="mux_failed",
+                        message=f"mkvmerge exited with code {returncode}",
+                        context={
+                            "returncode": returncode,
+                            "output_path": str(output_path),
+                            "errors": errors,
+                        },
+                    )
+                else:
+                    debug_logger.log(
+                        level="DEBUG",
+                        operation="mux_complete",
+                        message="mkvmerge muxing completed successfully",
+                        context={
+                            "output_path": str(output_path),
+                            "output_exists": output_path.exists() if output_path else False,
+                        },
+                    )
+
+            return output_path, returncode, errors
         finally:
             if chapters_path:
                 chapters_path.unlink()