diff --git a/Moonlight.ApiServer/Extensions/ZipArchiveExtensions.cs b/Moonlight.ApiServer/Extensions/ZipArchiveExtensions.cs
new file mode 100644
index 00000000..95c928d7
--- /dev/null
+++ b/Moonlight.ApiServer/Extensions/ZipArchiveExtensions.cs
@@ -0,0 +1,33 @@
+using System.IO.Compression;
+using System.Text;
+
+namespace Moonlight.ApiServer.Extensions;
+
+public static class ZipArchiveExtensions
+{
+    public static async Task AddBinary(this ZipArchive archive, string name, byte[] bytes)
+    {
+        var entry = archive.CreateEntry(name);
+        await using var dataStream = entry.Open();
+        
+        await dataStream.WriteAsync(bytes);
+        await dataStream.FlushAsync();
+    }
+
+    public static async Task AddText(this ZipArchive archive, string name, string content)
+    {
+        var data = Encoding.UTF8.GetBytes(content);
+        await archive.AddBinary(name, data);
+    }
+
+    public static async Task AddFile(this ZipArchive archive, string name, string path)
+    {
+        var fs = File.Open(path, FileMode.Open, FileAccess.Read, FileShare.ReadWrite);
+        
+        var entry = archive.CreateEntry(name);
+        await using var dataStream = entry.Open();
+
+        await fs.CopyToAsync(dataStream);
+        await dataStream.FlushAsync();
+    }
+}
\ No newline at end of file
diff --git a/Moonlight.ApiServer/Http/Controllers/Admin/Sys/DiagnoseController.cs b/Moonlight.ApiServer/Http/Controllers/Admin/Sys/DiagnoseController.cs
new file mode 100644
index 00000000..94ae9d51
--- /dev/null
+++ b/Moonlight.ApiServer/Http/Controllers/Admin/Sys/DiagnoseController.cs
@@ -0,0 +1,41 @@
+using Microsoft.AspNetCore.Mvc;
+using MoonCore.Attributes;
+using Moonlight.ApiServer.Services;
+using Moonlight.Shared.Http.Requests.Admin.Sys;
+using Moonlight.Shared.Http.Responses.Admin.Sys;
+using Moonlight.Shared.Misc;
+
+
+namespace Moonlight.ApiServer.Http.Controllers.Admin.Sys;
+
+[ApiController]
+[Route("api/admin/system/diagnose")]
+[RequirePermission("admin.system.diagnose")]
+public class DiagnoseController : Controller
+{
+    private readonly DiagnoseService DiagnoseService;
+
+    public DiagnoseController(DiagnoseService diagnoseService)
+    {
+        DiagnoseService = diagnoseService;
+    }
+
+    [HttpPost]
+    public async Task Diagnose([FromBody] GenerateDiagnoseRequest request)
+    {
+        var stream = await DiagnoseService.GenerateDiagnose(request.Providers);
+        
+        await Results.Stream(
+                stream,
+                contentType: "application/zip",
+                fileDownloadName: "diagnose.zip"
+            )
+            .ExecuteAsync(HttpContext);
+    }
+
+    [HttpGet("providers")]
+    public async Task<DiagnoseProvideResponse[]> GetProviders()
+    {
+        return await DiagnoseService.GetProviders();
+    }
+}
\ No newline at end of file
diff --git a/Moonlight.ApiServer/Http/Controllers/Admin/Sys/SystemController.cs b/Moonlight.ApiServer/Http/Controllers/Admin/Sys/SystemController.cs
index b0c9f8d2..e69efc8f 100644
--- a/Moonlight.ApiServer/Http/Controllers/Admin/Sys/SystemController.cs
+++ b/Moonlight.ApiServer/Http/Controllers/Admin/Sys/SystemController.cs
@@ -1,5 +1,6 @@
 using Microsoft.AspNetCore.Mvc;
 using MoonCore.Attributes;
+using Moonlight.ApiServer.Interfaces;
 using Moonlight.ApiServer.Services;
 using Moonlight.Shared.Http.Responses.Admin.Sys;
 
@@ -10,10 +11,13 @@ namespace Moonlight.ApiServer.Http.Controllers.Admin.Sys;
 public class SystemController : Controller
 {
     private readonly ApplicationService ApplicationService;
+    private readonly IEnumerable<IDiagnoseProvider> DiagnoseProviders;
 
-    public SystemController(ApplicationService applicationService)
+
+    public SystemController(ApplicationService applicationService, IEnumerable<IDiagnoseProvider> diagnoseProviders)
     {
         ApplicationService = applicationService;
+        DiagnoseProviders = diagnoseProviders;
     }
 
     [HttpGet]
diff --git a/Moonlight.ApiServer/Implementations/Diagnose/CoreConfigDiagnoseProvider.cs b/Moonlight.ApiServer/Implementations/Diagnose/CoreConfigDiagnoseProvider.cs
new file mode 100644
index 00000000..689148aa
--- /dev/null
+++ b/Moonlight.ApiServer/Implementations/Diagnose/CoreConfigDiagnoseProvider.cs
@@ -0,0 +1,57 @@
+using System.IO.Compression;
+using System.Text.Json;
+using Moonlight.ApiServer.Configuration;
+using Moonlight.ApiServer.Extensions;
+using Moonlight.ApiServer.Interfaces;
+
+namespace Moonlight.ApiServer.Implementations.Diagnose;
+
+public class CoreConfigDiagnoseProvider : IDiagnoseProvider
+{
+    private readonly AppConfiguration Config;
+
+    public CoreConfigDiagnoseProvider(AppConfiguration config)
+    {
+        Config = config;
+    }
+
+    private string CheckForNullOrEmpty(string? content)
+    {
+        return string.IsNullOrEmpty(content)
+            ? "ISEMPTY"
+            : "ISNOTEMPTY";
+    }
+
+    public async Task ModifyZipArchive(ZipArchive archive)
+    {
+        var json = JsonSerializer.Serialize(Config);
+        var config = JsonSerializer.Deserialize<AppConfiguration>(json);
+
+        if (config == null)
+        {
+            await archive.AddText("core/config.txt", "Could not fetch config.");
+            return;
+        }
+
+        config.Database.Password = CheckForNullOrEmpty(config.Database.Password);
+
+        config.Authentication.OAuth2.ClientSecret = CheckForNullOrEmpty(config.Authentication.OAuth2.ClientSecret);
+
+        config.Authentication.OAuth2.Secret = CheckForNullOrEmpty(config.Authentication.OAuth2.Secret);
+
+        config.Authentication.Secret = CheckForNullOrEmpty(config.Authentication.Secret);
+
+        config.Authentication.OAuth2.ClientId = CheckForNullOrEmpty(config.Authentication.OAuth2.ClientId);
+
+        await archive.AddText(
+            "core/config.txt",
+            JsonSerializer.Serialize(
+                config,
+                new JsonSerializerOptions()
+                {
+                    WriteIndented = true
+                }
+            )
+        );
+    }
+}
\ No newline at end of file
diff --git a/Moonlight.ApiServer/Implementations/Diagnose/LogsDiagnoseProvider.cs b/Moonlight.ApiServer/Implementations/Diagnose/LogsDiagnoseProvider.cs
new file mode 100644
index 00000000..0ef1e82b
--- /dev/null
+++ b/Moonlight.ApiServer/Implementations/Diagnose/LogsDiagnoseProvider.cs
@@ -0,0 +1,22 @@
+using System.IO.Compression;
+using Moonlight.ApiServer.Extensions;
+using Moonlight.ApiServer.Interfaces;
+
+namespace Moonlight.ApiServer.Implementations.Diagnose;
+
+public class LogsDiagnoseProvider : IDiagnoseProvider
+{
+    public async Task ModifyZipArchive(ZipArchive archive)
+    {
+        var path = Path.Combine("storage", "logs", "latest.log");
+
+        if (!File.Exists(path))
+        {
+            await archive.AddText("logs.txt", "Logs file latest.log has not been found");
+            return;
+        }
+        
+        var logsContent = await File.ReadAllTextAsync(path);
+        await archive.AddText("logs.txt", logsContent);
+    }
+}
\ No newline at end of file
diff --git a/Moonlight.ApiServer/Implementations/Startup/CoreStartup.cs b/Moonlight.ApiServer/Implementations/Startup/CoreStartup.cs
index b5293345..3f27ab65 100644
--- a/Moonlight.ApiServer/Implementations/Startup/CoreStartup.cs
+++ b/Moonlight.ApiServer/Implementations/Startup/CoreStartup.cs
@@ -1,6 +1,8 @@
 using Microsoft.OpenApi.Models;
 using Moonlight.ApiServer.Configuration;
 using Moonlight.ApiServer.Database;
+using Moonlight.ApiServer.Implementations.Diagnose;
+using Moonlight.ApiServer.Interfaces;
 using Moonlight.ApiServer.Plugins;
 
 namespace Moonlight.ApiServer.Implementations.Startup;
@@ -44,6 +46,13 @@ public class CoreStartup : IPluginStartup
 
         builder.Services.AddDbContext<CoreDataContext>();
 
+        #endregion
+
+        #region Diagnose
+
+        builder.Services.AddSingleton<IDiagnoseProvider, CoreConfigDiagnoseProvider>();
+        builder.Services.AddSingleton<IDiagnoseProvider, LogsDiagnoseProvider>();
+
         #endregion
         
         return Task.CompletedTask;
diff --git a/Moonlight.ApiServer/Interfaces/IDiagnoseProvider.cs b/Moonlight.ApiServer/Interfaces/IDiagnoseProvider.cs
new file mode 100644
index 00000000..5a4a9cf2
--- /dev/null
+++ b/Moonlight.ApiServer/Interfaces/IDiagnoseProvider.cs
@@ -0,0 +1,8 @@
+using System.IO.Compression;
+
+namespace Moonlight.ApiServer.Interfaces;
+
+public interface IDiagnoseProvider
+{
+    public Task ModifyZipArchive(ZipArchive archive);
+}
\ No newline at end of file
diff --git a/Moonlight.ApiServer/Services/DiagnoseService.cs b/Moonlight.ApiServer/Services/DiagnoseService.cs
new file mode 100644
index 00000000..a5844b04
--- /dev/null
+++ b/Moonlight.ApiServer/Services/DiagnoseService.cs
@@ -0,0 +1,95 @@
+using Moonlight.ApiServer.Interfaces;
+using System.IO.Compression;
+using MoonCore.Attributes;
+using MoonCore.Exceptions;
+using Moonlight.Shared.Http.Responses.Admin.Sys;
+
+namespace Moonlight.ApiServer.Services;
+
+[Scoped]
+public class DiagnoseService
+{
+    private readonly IEnumerable<IDiagnoseProvider> DiagnoseProviders;
+    private readonly ILogger<DiagnoseService> Logger;
+
+    public DiagnoseService(
+        IEnumerable<IDiagnoseProvider> diagnoseProviders,
+        ILogger<DiagnoseService> logger
+    )
+    {
+        DiagnoseProviders = diagnoseProviders;
+        Logger = logger;
+    }
+
+    public Task<DiagnoseProvideResponse[]> GetProviders()
+    {
+        var availableProviders = new List<DiagnoseProvideResponse>();
+
+        foreach (var diagnoseProvider in DiagnoseProviders)
+        {
+            var name = diagnoseProvider.GetType().Name;
+
+            var type = diagnoseProvider.GetType().FullName;
+
+            // The type name is null if the type is a generic type, unlikely, but still could happen
+            if (type == null)
+                continue;
+
+            availableProviders.Add(new DiagnoseProvideResponse()
+            {
+                Name = name,
+                Type = type
+            });
+        }
+
+        return Task.FromResult(
+            availableProviders.ToArray()
+        );
+    }
+
+    public async Task<MemoryStream> GenerateDiagnose(string[] requestedProviders)
+    {
+        IDiagnoseProvider[] providers;
+
+        if (requestedProviders.Length == 0)
+            providers = DiagnoseProviders.ToArray();
+        else
+        {
+            var foundProviders = new List<IDiagnoseProvider>();
+
+            foreach (var requestedProvider in requestedProviders)
+            {
+                var provider = DiagnoseProviders.FirstOrDefault(x => x.GetType().FullName == requestedProvider);
+
+                if (provider == null)
+                    continue;
+
+                foundProviders.Add(provider);
+            }
+
+            providers = foundProviders.ToArray();
+        }
+
+        try
+        {
+            var outputStream = new MemoryStream();
+            var zipArchive = new ZipArchive(outputStream, ZipArchiveMode.Create, leaveOpen: true);
+
+            foreach (var provider in providers)
+            {
+                await provider.ModifyZipArchive(zipArchive);
+            }
+            
+            zipArchive.Dispose();
+
+            outputStream.Position = 0;
+            return outputStream;
+        }
+        catch (Exception e)
+        {
+            Logger.LogError("An unhandled error occured while generated the diagnose file: {e}", e);
+
+            throw new HttpApiException("An unhandled error occured while generating the diagnose file", 500);
+        }
+    }
+}
\ No newline at end of file
diff --git a/Moonlight.ApiServer/Startup.cs b/Moonlight.ApiServer/Startup.cs
index 84695cc1..f9f4a00a 100644
--- a/Moonlight.ApiServer/Startup.cs
+++ b/Moonlight.ApiServer/Startup.cs
@@ -110,6 +110,7 @@ public class Startup
     private Task CreateStorage()
     {
         Directory.CreateDirectory("storage");
+        Directory.CreateDirectory(PathBuilder.Dir("storage", "logs"));
         Directory.CreateDirectory(PathBuilder.Dir("storage", "plugins"));
 
         return Task.CompletedTask;
@@ -338,7 +339,10 @@ public class Startup
         {
             configuration.Console.Enable = true;
             configuration.Console.EnableAnsiMode = true;
-            configuration.FileLogging.Enable = false;
+            configuration.FileLogging.Enable = true;
+            configuration.FileLogging.Path = PathBuilder.File("storage", "logs", "latest.log");
+            configuration.FileLogging.EnableLogRotation = true;
+            configuration.FileLogging.RotateLogNameTemplate = PathBuilder.File("storage", "logs", "apiserver.{0}.log");
         });
 
         LoggerFactory = new LoggerFactory();
diff --git a/Moonlight.Client/UI/Views/Admin/Sys/Diagnose.razor b/Moonlight.Client/UI/Views/Admin/Sys/Diagnose.razor
new file mode 100644
index 00000000..0a544f41
--- /dev/null
+++ b/Moonlight.Client/UI/Views/Admin/Sys/Diagnose.razor
@@ -0,0 +1,120 @@
+@page "/admin/system/diagnose"
+
+@using MoonCore.Attributes
+@using MoonCore.Helpers
+@using Moonlight.Shared.Http.Requests.Admin.Sys
+@using Moonlight.Shared.Http.Responses.Admin.Sys
+
+@attribute [RequirePermission("admin.system.diagnose")]
+
+@inject HttpApiClient ApiClient
+@inject DownloadService DownloadService
+
+<div class="mb-5">
+    <NavTabs Index="5" Names="UiConstants.AdminNavNames" Links="UiConstants.AdminNavLinks"/>
+</div>
+
+<div class="grid grid-cols-2">
+    <div class="col-span-2 md:col-span-1 card">
+        <div class="card-header">
+            <span class="card-title">Diagnose</span>
+        </div>
+        <div class="card-body">
+            <p>
+                If you're experiencing issues or need help via our Discord, you're in the right place here!
+                By pressing the button below, Moonlight will run all available diagnostic checks and package the results
+                into a
+                downloadable zip file.
+                The report includes useful information about your system, plugins, and environment, making it easier to
+                identify problems or share with support.
+            </p>
+
+            <WButton OnClick="GenerateDiagnose" CssClasses="btn btn-primary my-5">Generate diagnose</WButton>
+
+            <div class="text-sm">
+                <a class="text-primary cursor-pointer flex items-center" @onclick:preventDefault
+                   @onclick="ToggleDropDown">
+                    <span class="me-1.5">Advanced</span>
+                    @if (DropdownOpen)
+                    {
+                        <i class="icon-chevron-up"></i>
+                    }
+                    else
+                    {
+                        <i class="icon-chevron-down"></i>
+                    }
+                </a>
+
+                <div class="@(DropdownOpen ? "" : "hidden")">
+                    <LazyLoader Load="Load">
+                        <div class="mb-2 py-2 border-b border-gray-700 flex items-center gap-3">
+                            <input id="selectall_checkbox" @bind="SelectAll" type="checkbox" class="form-checkbox">
+                            <label for="selectall_checkbox">Select all</label>
+                        </div>
+
+                        @foreach (var item in AvailableProviders)
+                        {
+                            <div class="mt-1 flex gap-3 items-center">
+                                <input class="form-checkbox" type="checkbox" id="@(item.Key.Type + "_checkbox")"
+                                       @bind="@AvailableProviders[item.Key]"/>
+                                <label
+                                    for="@(item.Key.Type + "_checkbox")">@Formatter.ConvertCamelCaseToSpaces(item.Key.Name)</label>
+                            </div>
+                        }
+                    </LazyLoader>
+                </div>
+            </div>
+        </div>
+    </div>
+</div>
+
+@code
+{
+    private bool DropdownOpen = false;
+    private Dictionary<DiagnoseProvideResponse, bool> AvailableProviders;
+    
+    private bool SelectAll
+    {
+        get => AvailableProviders.Values.All(v => v);
+        set
+        {
+            foreach (var k in AvailableProviders.Keys)
+                AvailableProviders[k] = value;
+        }
+    }
+
+    private async Task Load(LazyLoader arg)
+    {
+        var providers = await ApiClient.GetJson<DiagnoseProvideResponse[]>(
+            "api/admin/system/diagnose/providers"
+        );
+
+        AvailableProviders = providers
+            .ToDictionary(x => x, _ => true);
+    }
+
+    private async Task GenerateDiagnose(WButton _)
+    {
+        var request = new GenerateDiagnoseRequest();
+
+        if (!SelectAll)
+        {
+            // filter the providers which have been selected if not all providers have been selected
+            request.Providers = AvailableProviders
+                .Where(x => x.Value)
+                .Select(x => x.Key.Type)
+                .ToArray();
+        }
+
+        var stream = await ApiClient.PostStream("api/admin/system/diagnose", request);
+
+        await DownloadService.DownloadStream("diagnose.zip", stream);
+    }
+
+
+    private async Task ToggleDropDown()
+    {
+        DropdownOpen = !DropdownOpen;
+        await InvokeAsync(StateHasChanged);
+    }
+}
\ No newline at end of file
diff --git a/Moonlight.Client/UiConstants.cs b/Moonlight.Client/UiConstants.cs
index 9293cc7f..dce82611 100644
--- a/Moonlight.Client/UiConstants.cs
+++ b/Moonlight.Client/UiConstants.cs
@@ -4,12 +4,12 @@ public static class UiConstants
 {
     public static readonly string[] AdminNavNames =
     [
-        "Overview", "Theme", "Files", "Hangfire", "Advanced"
+        "Overview", "Theme", "Files", "Hangfire", "Advanced", "Diagnose"
     ];
 
     public static readonly string[] AdminNavLinks =
     [
         "/admin/system", "/admin/system/theme", "/admin/system/files", "/admin/system/hangfire",
-        "/admin/system/advanced"
+        "/admin/system/advanced", "/admin/system/diagnose"
     ];
 }
\ No newline at end of file
diff --git a/Moonlight.Shared/Http/Requests/Admin/Sys/GenerateDiagnoseRequest.cs b/Moonlight.Shared/Http/Requests/Admin/Sys/GenerateDiagnoseRequest.cs
new file mode 100644
index 00000000..3757ab8e
--- /dev/null
+++ b/Moonlight.Shared/Http/Requests/Admin/Sys/GenerateDiagnoseRequest.cs
@@ -0,0 +1,6 @@
+namespace Moonlight.Shared.Http.Requests.Admin.Sys;
+
+public class GenerateDiagnoseRequest
+{
+    public string[] Providers { get; set; } = [];
+}
\ No newline at end of file
diff --git a/Moonlight.Shared/Http/Responses/Admin/Sys/DiagnoseProvideResponse.cs b/Moonlight.Shared/Http/Responses/Admin/Sys/DiagnoseProvideResponse.cs
new file mode 100644
index 00000000..6a23a991
--- /dev/null
+++ b/Moonlight.Shared/Http/Responses/Admin/Sys/DiagnoseProvideResponse.cs
@@ -0,0 +1,7 @@
+namespace Moonlight.Shared.Http.Responses.Admin.Sys;
+
+public class DiagnoseProvideResponse
+{
+    public string Name { get; set; }
+    public string Type { get; set; }
+}
\ No newline at end of file