diff --git a/CHANGELOG.md b/CHANGELOG.md
index b016e34b..1a7dd6f6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,12 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## [Unreleased]
 
+### Changed
+
+- Log files are restructured. They are now under `logs/cli`.
+- Log files are split. There is now a `verbose.log` and `debug.log` for every run. The time stamps
+  between the two will be identical.
+
 ## [4.3.0] - 2023-01-22
 
 ### Added
diff --git a/src/Recyclarr.Cli/Logging/LoggerFactory.cs b/src/Recyclarr.Cli/Logging/LoggerFactory.cs
index 544806e3..22ce25b4 100644
--- a/src/Recyclarr.Cli/Logging/LoggerFactory.cs
+++ b/src/Recyclarr.Cli/Logging/LoggerFactory.cs
@@ -1,4 +1,5 @@
 using System.IO.Abstractions;
+using Recyclarr.Common.Extensions;
 using Recyclarr.Common.Serilog;
 using Recyclarr.TrashLib;
 using Recyclarr.TrashLib.Startup;
@@ -47,13 +48,24 @@ public class LoggerFactory
 
     public ILogger Create()
     {
-        var logPath = _paths.LogDirectory.File($"trash_{DateTime.Now:yyyy-MM-dd_HH-mm-ss}.log");
+        var logFilePrefix = $"recyclarr_{DateTime.Now:yyyy-MM-dd_HH-mm-ss}";
+        var logDir = _paths.LogDirectory.SubDir("cli");
+
+        string LogFilePath(string type)
+        {
+            return logDir.File($"{logFilePrefix}.{type}.log").FullName;
+        }
 
         return new LoggerConfiguration()
-            .MinimumLevel.Is(LogEventLevel.Debug)
+            .MinimumLevel.Is(LogEventLevel.Verbose)
             .Enrich.With<ExceptionMessageEnricher>()
             .WriteTo.Console(GetConsoleTemplate(), levelSwitch: _levelSwitch)
-            .WriteTo.File(GetFileTemplate(), logPath.FullName)
+            .WriteTo.Logger(c => c
+                .MinimumLevel.Debug()
+                .WriteTo.File(GetFileTemplate(), LogFilePath("debug")))
+            .WriteTo.Logger(c => c
+                .Filter.ByIncludingOnly(e => e.Level == LogEventLevel.Verbose)
+                .WriteTo.File(GetFileTemplate(), LogFilePath("verbose")))
             .Enrich.FromLogContext()
             .CreateLogger();
     }
diff --git a/src/Recyclarr.Common/Extensions/FileSystemExtensions.cs b/src/Recyclarr.Common/Extensions/FileSystemExtensions.cs
index f4b128f8..897e27ca 100644
--- a/src/Recyclarr.Common/Extensions/FileSystemExtensions.cs
+++ b/src/Recyclarr.Common/Extensions/FileSystemExtensions.cs
@@ -62,4 +62,10 @@ public static class FileSystemExtensions
     {
         return Regex.Replace(path, $"^{Regex.Escape(oldDir)}", newDir);
     }
+
+    public static IDirectoryInfo SubDir(this IDirectoryInfo dir, params string[] subdirectories)
+    {
+        return subdirectories.Aggregate(dir,
+            (d, s) => d.FileSystem.DirectoryInfo.New(d.FileSystem.Path.Combine(d.FullName, s)));
+    }
 }
diff --git a/src/Recyclarr.TrashLib/Http/FlurlLogging.cs b/src/Recyclarr.TrashLib/Http/FlurlLogging.cs
index 500b0a01..322674f3 100644
--- a/src/Recyclarr.TrashLib/Http/FlurlLogging.cs
+++ b/src/Recyclarr.TrashLib/Http/FlurlLogging.cs
@@ -14,7 +14,7 @@ public static class FlurlLogging
         {
             var url = urlInterceptor(call.Request.Url.Clone());
             log.Debug("HTTP Request: {Method} {Url}", call.HttpRequestMessage.Method, url);
-            LogBody(log, call.RequestBody);
+            LogBody(log, url, call.RequestBody);
         };
 
         settings.AfterCallAsync = async call =>
@@ -26,7 +26,7 @@ public static class FlurlLogging
             var content = call.Response?.ResponseMessage.Content;
             if (content is not null)
             {
-                LogBody(log, await content.ReadAsStringAsync());
+                LogBody(log, url, await content.ReadAsStringAsync());
             }
         };
 
@@ -42,7 +42,7 @@ public static class FlurlLogging
         };
     }
 
-    private static void LogBody(ILogger log, string? body)
+    private static void LogBody(ILogger log, Url url, string? body)
     {
         if (body is null)
         {
@@ -50,7 +50,7 @@ public static class FlurlLogging
         }
 
         body = JsonConvert.SerializeObject(JsonConvert.DeserializeObject(body));
-        log.Debug("HTTP Body: {Body}", body);
+        log.Verbose("HTTP Body: {Url} {Body}", url, body);
     }
 
     public static Url SanitizeUrl(Url url)