diff --git a/Dalamud/EntryPoint.cs b/Dalamud/EntryPoint.cs
index 33e09e221..26ff396d1 100644
--- a/Dalamud/EntryPoint.cs
+++ b/Dalamud/EntryPoint.cs
@@ -8,6 +8,7 @@ using System.Threading.Tasks;
 
 using Dalamud.Configuration.Internal;
 using Dalamud.Logging.Internal;
+using Dalamud.Logging.Retention;
 using Dalamud.Plugin.Internal;
 using Dalamud.Support;
 using Dalamud.Utility;
@@ -88,58 +89,35 @@ public sealed class EntryPoint
         var logFileName = logName.IsNullOrEmpty() ? "dalamud" : $"dalamud-{logName}";
 
 #if DEBUG
-        var logPath = Path.Combine(baseDirectory, $"{logFileName}.log");
-        var oldPath = Path.Combine(baseDirectory, $"{logFileName}.old.log");
-        var oldPathOld = Path.Combine(baseDirectory, $"{logFileName}.log.old");
+        var logPath = new FileInfo(Path.Combine(baseDirectory, $"{logFileName}.log"));
+        var oldPath = new FileInfo(Path.Combine(baseDirectory, $"{logFileName}.old.log"));
 #else
         var logPath = Path.Combine(baseDirectory, "..", "..", "..", $"{logFileName}.log");
         var oldPath = Path.Combine(baseDirectory, "..", "..", "..", $"{logFileName}.old.log");
-        var oldPathOld = Path.Combine(baseDirectory, "..", "..", "..", $"{logFileName}.log.old");
 #endif
         Log.CloseAndFlush();
-        
-#if DEBUG
-        var oldFileOld = new FileInfo(oldPathOld);
-        if (oldFileOld.Exists)
-        {
-            var oldFile = new FileInfo(oldPath);
-            if (oldFile.Exists)
-                oldFileOld.Delete();
-            else
-                oldFileOld.MoveTo(oldPath);
-        }
 
-        CullLogFile(logPath, 1 * 1024 * 1024, oldPath, 10 * 1024 * 1024);
+        RetentionBehaviour behaviour;
+#if DEBUG
+        behaviour = new DebugRetentionBehaviour();
 #else
-        try
-        {
-            if (File.Exists(logPath))
-                File.Delete(logPath);
-            
-            if (File.Exists(oldPath))
-                File.Delete(oldPath);
-            
-            if (File.Exists(oldPathOld))
-                File.Delete(oldPathOld);
-        }
-        catch
-        {
-            // ignored
-        }
+        behaviour = new ReleaseRetentionBehaviour();
 #endif
 
+        behaviour.Apply(logPath, oldPath);
+
         var config = new LoggerConfiguration()
                      .WriteTo.Sink(SerilogEventSink.Instance)
                      .MinimumLevel.ControlledBy(LogLevelSwitch);
 
         if (logSynchronously)
         {
-            config = config.WriteTo.File(logPath, fileSizeLimitBytes: null);
+            config = config.WriteTo.File(logPath.FullName, fileSizeLimitBytes: null);
         }
         else
         {
             config = config.WriteTo.Async(a => a.File(
-                                              logPath,
+                                              logPath.FullName,
                                               fileSizeLimitBytes: null,
                                               buffered: false,
                                               flushToDiskInterval: TimeSpan.FromSeconds(1)));
@@ -265,86 +243,6 @@ public sealed class EntryPoint
         }
     }
 
-    /// <summary>
-    /// Trim existing log file to a specified length, and optionally move the excess data to another file.
-    /// </summary>
-    /// <param name="logPath">Target log file to trim.</param>
-    /// <param name="logMaxSize">Maximum size of target log file.</param>
-    /// <param name="oldPath">.old file to move excess data to.</param>
-    /// <param name="oldMaxSize">Maximum size of .old file.</param>
-    private static void CullLogFile(string logPath, int logMaxSize, string oldPath, int oldMaxSize)
-    {
-        var logFile = new FileInfo(logPath);
-        var oldFile = new FileInfo(oldPath);
-        var targetFiles = new[]
-        {
-            (logFile, logMaxSize),
-            (oldFile, oldMaxSize),
-        };
-        var buffer = new byte[4096];
-
-        try
-        {
-            if (!logFile.Exists)
-                logFile.Create().Close();
-
-            // 1. Move excess data from logFile to oldFile
-            if (logFile.Length > logMaxSize)
-            {
-                using var reader = logFile.Open(FileMode.Open, FileAccess.Read, FileShare.ReadWrite);
-                using var writer = oldFile.Open(FileMode.Append, FileAccess.Write, FileShare.ReadWrite);
-
-                var amountToMove = (int)Math.Min(logFile.Length - logMaxSize, oldMaxSize);
-                reader.Seek(-(logMaxSize + amountToMove), SeekOrigin.End);
-
-                for (var i = 0; i < amountToMove; i += buffer.Length)
-                    writer.Write(buffer, 0, reader.Read(buffer, 0, Math.Min(buffer.Length, amountToMove - i)));
-            }
-
-            // 2. Cull each of .log and .old files
-            foreach (var (file, maxSize) in targetFiles)
-            {
-                if (!file.Exists || file.Length <= maxSize)
-                    continue;
-
-                using var reader = file.Open(FileMode.Open, FileAccess.Read, FileShare.ReadWrite);
-                using var writer = file.Open(FileMode.Open, FileAccess.Write, FileShare.ReadWrite);
-
-                reader.Seek(file.Length - maxSize, SeekOrigin.Begin);
-                for (int read; (read = reader.Read(buffer, 0, buffer.Length)) > 0;)
-                    writer.Write(buffer, 0, read);
-
-                writer.SetLength(maxSize);
-            }
-        }
-        catch (Exception ex)
-        {
-            if (ex is IOException)
-            {
-                foreach (var (file, _) in targetFiles)
-                {
-                    try
-                    {
-                        if (file.Exists)
-                            file.Delete();
-                    }
-                    catch (Exception ex2)
-                    {
-                        Log.Error(ex2, "Failed to delete {file}", file.FullName);
-                    }
-                }
-            }
-
-            Log.Error(ex, "Log cull failed");
-
-            /*
-            var caption = "XIVLauncher Error";
-            var message = $"Log cull threw an exception: {ex.Message}\n{ex.StackTrace ?? string.Empty}";
-            _ = MessageBoxW(IntPtr.Zero, message, caption, MessageBoxType.IconError | MessageBoxType.Ok);
-            */
-        }
-    }
-
     private static void OnUnhandledException(object sender, UnhandledExceptionEventArgs args)
     {
         switch (args.ExceptionObject)
diff --git a/Dalamud/Logging/Retention/DebugRetentionBehaviour.cs b/Dalamud/Logging/Retention/DebugRetentionBehaviour.cs
new file mode 100644
index 000000000..719ff8ece
--- /dev/null
+++ b/Dalamud/Logging/Retention/DebugRetentionBehaviour.cs
@@ -0,0 +1,15 @@
+using System.IO;
+
+namespace Dalamud.Logging.Retention;
+
+/// <summary>
+/// Class implementing log retention behaviour for debug builds.
+/// </summary>
+internal class DebugRetentionBehaviour : RetentionBehaviour
+{
+    /// <inheritdoc/>
+    public override void Apply(FileInfo logFile, FileInfo rolloverFile)
+    {
+        CullLogFile(logFile, 1 * 1024 * 1024, rolloverFile, 10 * 1024 * 1024);
+    }
+}
diff --git a/Dalamud/Logging/Retention/ReleaseRetentionBehaviour.cs b/Dalamud/Logging/Retention/ReleaseRetentionBehaviour.cs
new file mode 100644
index 000000000..79f272c46
--- /dev/null
+++ b/Dalamud/Logging/Retention/ReleaseRetentionBehaviour.cs
@@ -0,0 +1,15 @@
+using System.IO;
+
+namespace Dalamud.Logging.Retention;
+
+/// <summary>
+/// Class implementing log retention behaviour for release builds.
+/// </summary>
+internal class ReleaseRetentionBehaviour : RetentionBehaviour
+{
+    /// <inheritdoc/>
+    public override void Apply(FileInfo logFile, FileInfo rolloverFile)
+    {
+        CullLogFile(logFile, 0, rolloverFile, 10 * 1024 * 1024);
+    }
+}
diff --git a/Dalamud/Logging/Retention/RetentionBehaviour.cs b/Dalamud/Logging/Retention/RetentionBehaviour.cs
new file mode 100644
index 000000000..66c4c5f97
--- /dev/null
+++ b/Dalamud/Logging/Retention/RetentionBehaviour.cs
@@ -0,0 +1,91 @@
+using System;
+using System.IO;
+
+using Serilog;
+
+namespace Dalamud.Logging.Retention;
+
+/// <summary>
+/// Class implementing retention behaviour for log files.
+/// </summary>
+internal abstract class RetentionBehaviour
+{
+    /// <summary>
+    /// Apply the specified retention behaviour to log files.
+    /// </summary>
+    /// <param name="logFile">The regular log file path.</param>
+    /// <param name="rolloverFile">The rollover "old" log file path.</param>
+    public abstract void Apply(FileInfo logFile, FileInfo rolloverFile);
+    
+    /// <summary>
+    /// Trim existing log file to a specified length, and optionally move the excess data to another file.
+    /// </summary>
+    /// <param name="logFile">Target log file to trim.</param>
+    /// <param name="logMaxSize">Maximum size of target log file.</param>
+    /// <param name="oldFile">.old file to move excess data to.</param>
+    /// <param name="oldMaxSize">Maximum size of .old file.</param>
+    protected static void CullLogFile(FileInfo logFile, int logMaxSize, FileInfo oldFile, int oldMaxSize)
+    {
+        var targetFiles = new[]
+        {
+            (logFile, logMaxSize),
+            (oldFile, oldMaxSize),
+        };
+        var buffer = new byte[4096];
+
+        try
+        {
+            if (!logFile.Exists)
+                logFile.Create().Close();
+
+            // 1. Move excess data from logFile to oldFile
+            if (logFile.Length > logMaxSize)
+            {
+                using var reader = logFile.Open(FileMode.Open, FileAccess.Read, FileShare.ReadWrite);
+                using var writer = oldFile.Open(FileMode.Append, FileAccess.Write, FileShare.ReadWrite);
+
+                var amountToMove = (int)Math.Min(logFile.Length - logMaxSize, oldMaxSize);
+                reader.Seek(-(logMaxSize + amountToMove), SeekOrigin.End);
+
+                for (var i = 0; i < amountToMove; i += buffer.Length)
+                    writer.Write(buffer, 0, reader.Read(buffer, 0, Math.Min(buffer.Length, amountToMove - i)));
+            }
+
+            // 2. Cull each of .log and .old files
+            foreach (var (file, maxSize) in targetFiles)
+            {
+                if (!file.Exists || file.Length <= maxSize)
+                    continue;
+
+                using var reader = file.Open(FileMode.Open, FileAccess.Read, FileShare.ReadWrite);
+                using var writer = file.Open(FileMode.Open, FileAccess.Write, FileShare.ReadWrite);
+
+                reader.Seek(file.Length - maxSize, SeekOrigin.Begin);
+                for (int read; (read = reader.Read(buffer, 0, buffer.Length)) > 0;)
+                    writer.Write(buffer, 0, read);
+
+                writer.SetLength(maxSize);
+            }
+        }
+        catch (Exception ex)
+        {
+            if (ex is IOException)
+            {
+                foreach (var (file, _) in targetFiles)
+                {
+                    try
+                    {
+                        if (file.Exists)
+                            file.Delete();
+                    }
+                    catch (Exception ex2)
+                    {
+                        Log.Error(ex2, "Failed to delete {file}", file.FullName);
+                    }
+                }
+            }
+
+            Log.Error(ex, "Log cull failed");
+        }
+    }
+}