diff --git a/Jellyfin.Api/Controllers/DynamicHlsController.cs b/Jellyfin.Api/Controllers/DynamicHlsController.cs
index 590cdc33f0..d70c51b86f 100644
--- a/Jellyfin.Api/Controllers/DynamicHlsController.cs
+++ b/Jellyfin.Api/Controllers/DynamicHlsController.cs
@@ -1604,7 +1604,7 @@ public class DynamicHlsController : BaseJellyfinApiController
                 Path.GetFileNameWithoutExtension(outputPath));
         }
 
-        var hlsArguments = GetHlsArguments(isEventPlaylist, state.SegmentLength);
+        var hlsArguments = string.Format(CultureInfo.InvariantCulture, "-hls_playlist_type {0} -hls_list_size 0", isEventPlaylist ? "event" : "vod");
 
         return string.Format(
             CultureInfo.InvariantCulture,
@@ -1625,33 +1625,6 @@ public class DynamicHlsController : BaseJellyfinApiController
             EncodingUtils.NormalizePath(outputPath)).Trim();
     }
 
-    /// <summary>
-    /// Gets the HLS arguments for transcoding.
-    /// </summary>
-    /// <returns>The command line arguments for HLS transcoding.</returns>
-    private string GetHlsArguments(bool isEventPlaylist, int segmentLength)
-    {
-        var enableThrottling = _encodingOptions.EnableThrottling;
-        var enableSegmentDeletion = _encodingOptions.EnableSegmentDeletion;
-
-        // Only enable segment deletion when throttling is enabled
-        if (enableThrottling && enableSegmentDeletion)
-        {
-            // Store enough segments for configured seconds of playback; this needs to be above throttling settings
-            var segmentCount = _encodingOptions.SegmentKeepSeconds / segmentLength;
-
-            _logger.LogDebug("Using throttling and segment deletion, keeping {0} segments", segmentCount);
-
-            return string.Format(CultureInfo.InvariantCulture, "-hls_list_size {0} -hls_flags delete_segments", segmentCount.ToString(CultureInfo.InvariantCulture));
-        }
-        else
-        {
-            _logger.LogDebug("Using normal playback, is event playlist? {0}", isEventPlaylist);
-
-            return string.Format(CultureInfo.InvariantCulture, "-hls_playlist_type {0} -hls_list_size 0", isEventPlaylist ? "event" : "vod");
-        }
-    }
-
     /// <summary>
     /// Gets the audio arguments for transcoding.
     /// </summary>
diff --git a/MediaBrowser.Controller/MediaEncoding/TranscodingJob.cs b/MediaBrowser.Controller/MediaEncoding/TranscodingJob.cs
index 1e6d5933c8..2b6540ea88 100644
--- a/MediaBrowser.Controller/MediaEncoding/TranscodingJob.cs
+++ b/MediaBrowser.Controller/MediaEncoding/TranscodingJob.cs
@@ -136,6 +136,11 @@ public sealed class TranscodingJob : IDisposable
     /// </summary>
     public TranscodingThrottler? TranscodingThrottler { get; set; }
 
+    /// <summary>
+    /// Gets or sets transcoding segment cleaner.
+    /// </summary>
+    public TranscodingSegmentCleaner? TranscodingSegmentCleaner { get; set; }
+
     /// <summary>
     /// Gets or sets last ping date.
     /// </summary>
@@ -239,6 +244,7 @@ public sealed class TranscodingJob : IDisposable
         {
 #pragma warning disable CA1849 // Can't await in lock block
             TranscodingThrottler?.Stop().GetAwaiter().GetResult();
+            TranscodingSegmentCleaner?.Stop();
 
             var process = Process;
 
@@ -276,5 +282,7 @@ public sealed class TranscodingJob : IDisposable
         CancellationTokenSource = null;
         TranscodingThrottler?.Dispose();
         TranscodingThrottler = null;
+        TranscodingSegmentCleaner?.Dispose();
+        TranscodingSegmentCleaner = null;
     }
 }
diff --git a/MediaBrowser.Controller/MediaEncoding/TranscodingSegmentCleaner.cs b/MediaBrowser.Controller/MediaEncoding/TranscodingSegmentCleaner.cs
new file mode 100644
index 0000000000..6cbda8e0a7
--- /dev/null
+++ b/MediaBrowser.Controller/MediaEncoding/TranscodingSegmentCleaner.cs
@@ -0,0 +1,188 @@
+using System;
+using System.Collections.Generic;
+using System.IO;
+using System.Linq;
+using System.Threading;
+using System.Threading.Tasks;
+using MediaBrowser.Common.Configuration;
+using MediaBrowser.Model.Configuration;
+using MediaBrowser.Model.IO;
+using Microsoft.Extensions.Logging;
+
+namespace MediaBrowser.Controller.MediaEncoding;
+
+/// <summary>
+/// Transcoding segment cleaner.
+/// </summary>
+public class TranscodingSegmentCleaner : IDisposable
+{
+    private readonly TranscodingJob _job;
+    private readonly ILogger<TranscodingSegmentCleaner> _logger;
+    private readonly IConfigurationManager _config;
+    private readonly IFileSystem _fileSystem;
+    private readonly IMediaEncoder _mediaEncoder;
+    private Timer? _timer;
+    private int _segmentLength;
+
+    /// <summary>
+    /// Initializes a new instance of the <see cref="TranscodingSegmentCleaner"/> class.
+    /// </summary>
+    /// <param name="job">Transcoding job dto.</param>
+    /// <param name="logger">Instance of the <see cref="ILogger{TranscodingSegmentCleaner}"/> interface.</param>
+    /// <param name="config">Instance of the <see cref="IConfigurationManager"/> interface.</param>
+    /// <param name="fileSystem">Instance of the <see cref="IFileSystem"/> interface.</param>
+    /// <param name="mediaEncoder">Instance of the <see cref="IMediaEncoder"/> interface.</param>
+    /// <param name="segmentLength">The segment length of this transcoding job.</param>
+    public TranscodingSegmentCleaner(TranscodingJob job, ILogger<TranscodingSegmentCleaner> logger, IConfigurationManager config, IFileSystem fileSystem, IMediaEncoder mediaEncoder, int segmentLength)
+    {
+        _job = job;
+        _logger = logger;
+        _config = config;
+        _fileSystem = fileSystem;
+        _mediaEncoder = mediaEncoder;
+        _segmentLength = segmentLength;
+    }
+
+    /// <summary>
+    /// Start timer.
+    /// </summary>
+    public void Start()
+    {
+        _timer = new Timer(TimerCallback, null, 20000, 20000);
+    }
+
+    /// <summary>
+    /// Stop cleaner.
+    /// </summary>
+    public void Stop()
+    {
+        DisposeTimer();
+    }
+
+    /// <summary>
+    /// Dispose cleaner.
+    /// </summary>
+    public void Dispose()
+    {
+        Dispose(true);
+        GC.SuppressFinalize(this);
+    }
+
+    /// <summary>
+    /// Dispose cleaner.
+    /// </summary>
+    /// <param name="disposing">Disposing.</param>
+    protected virtual void Dispose(bool disposing)
+    {
+        if (disposing)
+        {
+            DisposeTimer();
+        }
+    }
+
+    private EncodingOptions GetOptions()
+    {
+        return _config.GetEncodingOptions();
+    }
+
+    private async void TimerCallback(object? state)
+    {
+        if (_job.HasExited)
+        {
+            DisposeTimer();
+            return;
+        }
+
+        var options = GetOptions();
+        var enableSegmentDeletion = options.EnableSegmentDeletion;
+        var segmentKeepSeconds = Math.Max(options.SegmentKeepSeconds, 20);
+
+        if (enableSegmentDeletion)
+        {
+            var downloadPositionTicks = _job.DownloadPositionTicks ?? 0;
+            var downloadPositionSeconds = Convert.ToInt64(TimeSpan.FromTicks(downloadPositionTicks).TotalSeconds);
+
+            if (downloadPositionSeconds > 0 && segmentKeepSeconds > 0 && downloadPositionSeconds > segmentKeepSeconds)
+            {
+                var idxMaxToRemove = (downloadPositionSeconds - segmentKeepSeconds) / _segmentLength;
+
+                if (idxMaxToRemove > 0)
+                {
+                    await DeleteSegmentFiles(_job, 0, idxMaxToRemove, 0, 1500).ConfigureAwait(false);
+                }
+            }
+        }
+    }
+
+    private async Task DeleteSegmentFiles(TranscodingJob job, long idxMin, long idxMax, int retryCount, int delayMs)
+    {
+        if (retryCount >= 10)
+        {
+            return;
+        }
+
+        var path = job.Path ?? throw new ArgumentException("Path can't be null.");
+
+        _logger.LogDebug("Deleting segment file(s) index {Min} to {Max} from {Path}", idxMin, idxMax, path);
+
+        await Task.Delay(delayMs).ConfigureAwait(false);
+
+        try
+        {
+            if (job.Type == TranscodingJobType.Hls)
+            {
+                DeleteHlsSegmentFiles(path, idxMin, idxMax);
+            }
+        }
+        catch (IOException ex)
+        {
+            _logger.LogError(ex, "Error deleting segment file(s) {Path}", path);
+
+            await DeleteSegmentFiles(job, idxMin, idxMax, retryCount + 1, 500).ConfigureAwait(false);
+        }
+        catch (Exception ex)
+        {
+            _logger.LogError(ex, "Error deleting segment file(s) {Path}", path);
+        }
+    }
+
+    private void DeleteHlsSegmentFiles(string outputFilePath, long idxMin, long idxMax)
+    {
+        var directory = Path.GetDirectoryName(outputFilePath)
+                        ?? throw new ArgumentException("Path can't be a root directory.", nameof(outputFilePath));
+
+        var name = Path.GetFileNameWithoutExtension(outputFilePath);
+
+        var filesToDelete = _fileSystem.GetFilePaths(directory)
+            .Where(f => long.TryParse(Path.GetFileNameWithoutExtension(f).Replace(name, string.Empty, StringComparison.Ordinal), out var idx) && idx >= idxMin && idx <= idxMax);
+
+        List<Exception>? exs = null;
+        foreach (var file in filesToDelete)
+        {
+            try
+            {
+                _logger.LogDebug("Deleting HLS segment file {0}", file);
+                _fileSystem.DeleteFile(file);
+            }
+            catch (IOException ex)
+            {
+                (exs ??= new List<Exception>(4)).Add(ex);
+                _logger.LogError(ex, "Error deleting HLS segment file {Path}", file);
+            }
+        }
+
+        if (exs is not null)
+        {
+            throw new AggregateException("Error deleting HLS segment files", exs);
+        }
+    }
+
+    private void DisposeTimer()
+    {
+        if (_timer is not null)
+        {
+            _timer.Dispose();
+            _timer = null;
+        }
+    }
+}
diff --git a/MediaBrowser.MediaEncoding/Transcoding/TranscodeManager.cs b/MediaBrowser.MediaEncoding/Transcoding/TranscodeManager.cs
index 8bace15c65..2a72cacdc9 100644
--- a/MediaBrowser.MediaEncoding/Transcoding/TranscodeManager.cs
+++ b/MediaBrowser.MediaEncoding/Transcoding/TranscodeManager.cs
@@ -546,6 +546,7 @@ public sealed class TranscodeManager : ITranscodeManager, IDisposable
         if (!transcodingJob.HasExited)
         {
             StartThrottler(state, transcodingJob);
+            StartSegmentCleaner(state, transcodingJob);
         }
         else if (transcodingJob.ExitCode != 0)
         {
@@ -573,6 +574,22 @@ public sealed class TranscodeManager : ITranscodeManager, IDisposable
            && state.IsInputVideo
            && state.VideoType == VideoType.VideoFile;
 
+    private void StartSegmentCleaner(StreamState state, TranscodingJob transcodingJob)
+    {
+        if (EnableSegmentCleaning(state))
+        {
+            transcodingJob.TranscodingSegmentCleaner = new TranscodingSegmentCleaner(transcodingJob, _loggerFactory.CreateLogger<TranscodingSegmentCleaner>(), _serverConfigurationManager, _fileSystem, _mediaEncoder, state.SegmentLength);
+            transcodingJob.TranscodingSegmentCleaner.Start();
+        }
+    }
+
+    private static bool EnableSegmentCleaning(StreamState state)
+        => state.InputProtocol is MediaProtocol.File or MediaProtocol.Http
+           && state.IsInputVideo
+           && state.TranscodingType == TranscodingJobType.Hls
+           && state.RunTimeTicks.HasValue
+           && state.RunTimeTicks.Value >= TimeSpan.FromMinutes(5).Ticks;
+
     private TranscodingJob OnTranscodeBeginning(
         string path,
         string? playSessionId,