diff --git a/LightlessSync/FileCache/FileCompactor.cs b/LightlessSync/FileCache/FileCompactor.cs
index 2e32a3e..a8170f4 100644
--- a/LightlessSync/FileCache/FileCompactor.cs
+++ b/LightlessSync/FileCache/FileCompactor.cs
@@ -1,6 +1,5 @@
 using LightlessSync.LightlessConfiguration;
 using LightlessSync.Services;
-using LightlessSync.Utils;
 using Microsoft.Extensions.Logging;
 using System.Collections.Concurrent;
 using System.Diagnostics;
@@ -191,6 +190,16 @@ public sealed class FileCompactor : IDisposable
         }
     }
 
+    private static string ConvertWinePathToLinux(string winePath)
+    {
+        if (winePath.StartsWith("Z:\\", StringComparison.OrdinalIgnoreCase))
+            return "/" + winePath.Substring(3).Replace('\\', '/');
+        if (winePath.StartsWith("C:\\", StringComparison.OrdinalIgnoreCase))
+            return Path.Combine(Environment.GetFolderPath(Environment.SpecialFolder.Personal),
+                winePath.Substring(3).Replace('\\', '/')).Replace('\\', '/');
+        return winePath.Replace('\\', '/');
+    }
+
     [DllImport("kernel32.dll")]
     private static extern int DeviceIoControl(IntPtr hDevice, uint dwIoControlCode, IntPtr lpInBuffer, uint nInBufferSize, IntPtr lpOutBuffer, uint nOutBufferSize, out IntPtr lpBytesReturned, out IntPtr lpOverlapped);
 
@@ -347,18 +356,42 @@ public sealed class FileCompactor : IDisposable
                 var mountOptions = GetMountOptionsForPath(path);
                 if (mountOptions.Contains("compress", StringComparison.OrdinalIgnoreCase))
                 {
-                    _logger.LogWarning("Cannot safely decompress {file}: filesystem mounted with compression ({opts}). Remount with 'compress=no' before running decompression.", path, mountOptions);
+                    _logger.LogWarning(
+                        "Cannot safely decompress {file}: filesystem mounted with compression ({opts}). Remount with 'compress=no' before running decompression.",
+                        path, mountOptions);
                     return;
                 }
 
-                _logger.LogDebug("Rewriting {file} to remove btrfs compression...", path);
-
-                var psi = new ProcessStartInfo("btrfs", $"filesystem defragment -- \"{path}\"")
+                string realPath = path;
+                bool isWine = _dalamudUtilService?.IsWine ?? false;
+                if (isWine)
                 {
+                    if (path.StartsWith("Z:\\", StringComparison.OrdinalIgnoreCase))
+                    {
+                        realPath = "/" + path.Substring(3).Replace('\\', '/');
+                    }
+                    else if (path.StartsWith("C:\\", StringComparison.OrdinalIgnoreCase))
+                    {
+                        // fallback for Wine's C:\ mapping
+                        realPath = Path.Combine(
+                            Environment.GetFolderPath(Environment.SpecialFolder.Personal),
+                            path.Substring(3).Replace('\\', '/')
+                        ).Replace('\\', '/');
+                    }
+
+                    _logger.LogTrace("Detected Wine environment. Converted path for decompression: {realPath}", realPath);
+                }
+
+                string command = $"btrfs filesystem defragment -- \"{realPath}\"";
+                var psi = new ProcessStartInfo
+                {
+                    FileName = isWine ? "/bin/bash" : "btrfs",
+                    Arguments = isWine ? $"-c \"{command}\"" : $"filesystem defragment -- \"{realPath}\"",
                     RedirectStandardOutput = true,
                     RedirectStandardError = true,
                     UseShellExecute = false,
-                    CreateNoWindow = true
+                    CreateNoWindow = true,
+                    WorkingDirectory = "/"
                 };
 
                 using var proc = Process.Start(psi);
@@ -368,7 +401,7 @@ public sealed class FileCompactor : IDisposable
                     return;
                 }
 
-                //End stream of process to read the files
+                // 4️⃣ Read process output
                 var stdout = proc.StandardOutput.ReadToEnd();
                 var stderr = proc.StandardError.ReadToEnd();
                 proc.WaitForExit();
@@ -495,12 +528,36 @@ public sealed class FileCompactor : IDisposable
     {
         try
         {
-            var psi = new ProcessStartInfo("filefrag", $"-v \"{path}\"")
+            bool isWine = _dalamudUtilService?.IsWine ?? false;
+            string realPath = path;
+
+            if (isWine)
             {
+                if (path.StartsWith("Z:\\", StringComparison.OrdinalIgnoreCase))
+                {
+                    realPath = "/" + path.Substring(3).Replace('\\', '/');
+                }
+                else if (path.StartsWith("C:\\", StringComparison.OrdinalIgnoreCase))
+                {
+                    realPath = Path.Combine(
+                        Environment.GetFolderPath(Environment.SpecialFolder.Personal),
+                        path.Substring(3).Replace('\\', '/')
+                    ).Replace('\\', '/');
+                }
+
+                _logger.LogTrace("Detected Wine environment. Converted path for filefrag: {realPath}", realPath);
+            }
+
+            string command = $"filefrag -v -- \"{realPath}\"";
+            var psi = new ProcessStartInfo
+            {
+                FileName = isWine ? "/bin/bash" : "filefrag",
+                Arguments = isWine ? $"-c \"{command}\"" : $"-v -- \"{realPath}\"",
                 RedirectStandardOutput = true,
                 RedirectStandardError = true,
                 UseShellExecute = false,
-                CreateNoWindow = true
+                CreateNoWindow = true,
+                WorkingDirectory = "/"
             };
 
             using var proc = Process.Start(psi);
@@ -511,10 +568,17 @@ public sealed class FileCompactor : IDisposable
             }
 
             string output = proc.StandardOutput.ReadToEnd();
+            string stderr = proc.StandardError.ReadToEnd();
             proc.WaitForExit();
 
-            bool compressed = output.Contains("flags: compressed", StringComparison.OrdinalIgnoreCase);
+            if (proc.ExitCode != 0)
+            {
+                _logger.LogDebug("filefrag exited with {code} for {file}. stderr: {stderr}",
+                    proc.ExitCode, path, stderr);
+                return false;
+            }
 
+            bool compressed = output.Contains("flags: compressed", StringComparison.OrdinalIgnoreCase);
             _logger.LogTrace("Btrfs compression check for {file}: {compressed}", path, compressed);
             return compressed;
         }
@@ -567,7 +631,20 @@ public sealed class FileCompactor : IDisposable
     {
         try
         {
-            var psi = new ProcessStartInfo("btrfs", $"filesystem defragment -czstd -- \"{path}\"")
+            string realPath = path;
+            if (_dalamudUtilService.IsWine)
+            {
+                realPath = ConvertWinePathToLinux(path);
+                _logger.LogTrace("Detected Wine environment, remapped path: {realPath}", realPath);
+            }
+
+            if (!File.Exists("/usr/bin/btrfs") && !File.Exists("/bin/btrfs"))
+            {
+                _logger.LogWarning("Skipping Btrfs compression — btrfs binary not found");
+                return false;
+            }
+
+            var psi = new ProcessStartInfo("btrfs", $"filesystem defragment -czstd -- \"{realPath}\"")
             {
                 RedirectStandardOutput = true,
                 RedirectStandardError = true,
@@ -578,7 +655,7 @@ public sealed class FileCompactor : IDisposable
             using var proc = Process.Start(psi);
             if (proc == null)
             {
-                _logger.LogWarning("Failed to start btrfs process for {file}", path);
+                _logger.LogWarning("Failed to start btrfs process for {file}", realPath);
                 return false;
             }
 
@@ -588,7 +665,7 @@ public sealed class FileCompactor : IDisposable
 
             if (proc.ExitCode != 0)
             {
-                _logger.LogWarning("btrfs defrag returned {code} for {file}: {err}", proc.ExitCode, path, stderr);
+                _logger.LogWarning("btrfs defrag returned {code} for {file}: {err}", proc.ExitCode, realPath, stderr);
                 return false;
             }
 
@@ -597,7 +674,7 @@ public sealed class FileCompactor : IDisposable
         }
         catch (Exception ex)
         {
-            _logger.LogWarning(ex, "Error running btrfs defragment for {file}", path);
+            _logger.LogWarning(ex, "Error running btrfs defragment for {file}", realPath);
             return false;
         }
     }