diff --git a/PolyPilot.Tests/InstructionRecommendationHelperTests.cs b/PolyPilot.Tests/InstructionRecommendationHelperTests.cs
new file mode 100644
index 00000000..a5cf9525
--- /dev/null
+++ b/PolyPilot.Tests/InstructionRecommendationHelperTests.cs
@@ -0,0 +1,128 @@
+using PolyPilot.Models;
+
+namespace PolyPilot.Tests;
+
+public class InstructionRecommendationHelperTests
+{
+    [Fact]
+    public void BuildPrompt_NoArguments_ContainsBasicSections()
+    {
+        var prompt = InstructionRecommendationHelper.BuildRecommendationPrompt(null);
+
+        Assert.Contains("Copilot Instructions", prompt);
+        Assert.Contains("Skills", prompt);
+        Assert.Contains("Agents", prompt);
+        Assert.Contains("copilot-instructions.md", prompt);
+    }
+
+    [Fact]
+    public void BuildPrompt_WithWorkingDirectory_IncludesDirectory()
+    {
+        var prompt = InstructionRecommendationHelper.BuildRecommendationPrompt("/home/user/myproject");
+
+        Assert.Contains("/home/user/myproject", prompt);
+    }
+
+    [Fact]
+    public void BuildPrompt_WithRepoName_IncludesRepoName()
+    {
+        var prompt = InstructionRecommendationHelper.BuildRecommendationPrompt(
+            "/home/user/myproject", repoName: "MyOrg/MyRepo");
+
+        Assert.Contains("MyOrg/MyRepo", prompt);
+    }
+
+    [Fact]
+    public void BuildPrompt_WithExistingSkills_ListsThem()
+    {
+        var skills = new List<(string Name, string Description)>
+        {
+            ("build", "Build the project"),
+            ("test", "Run tests")
+        };
+
+        var prompt = InstructionRecommendationHelper.BuildRecommendationPrompt(
+            "/project", existingSkills: skills);
+
+        Assert.Contains("Currently configured skills", prompt);
+        Assert.Contains("**build**", prompt);
+        Assert.Contains("Build the project", prompt);
+        Assert.Contains("**test**", prompt);
+        Assert.Contains("Run tests", prompt);
+    }
+
+    [Fact]
+    public void BuildPrompt_WithExistingAgents_ListsThem()
+    {
+        var agents = new List<(string Name, string Description)>
+        {
+            ("reviewer", "Code review agent"),
+            ("docs", "")
+        };
+
+        var prompt = InstructionRecommendationHelper.BuildRecommendationPrompt(
+            "/project", existingAgents: agents);
+
+        Assert.Contains("Currently configured agents", prompt);
+        Assert.Contains("**reviewer**", prompt);
+        Assert.Contains("Code review agent", prompt);
+        Assert.Contains("**docs**", prompt);
+    }
+
+    [Fact]
+    public void BuildPrompt_NoSkillsOrAgents_DoesNotListSections()
+    {
+        var prompt = InstructionRecommendationHelper.BuildRecommendationPrompt("/project");
+
+        Assert.DoesNotContain("Currently configured skills", prompt);
+        Assert.DoesNotContain("Currently configured agents", prompt);
+    }
+
+    [Fact]
+    public void BuildPrompt_EmptySkillsAndAgents_DoesNotListSections()
+    {
+        var skills = new List<(string Name, string Description)>();
+        var agents = new List<(string Name, string Description)>();
+
+        var prompt = InstructionRecommendationHelper.BuildRecommendationPrompt(
+            "/project", existingSkills: skills, existingAgents: agents);
+
+        Assert.DoesNotContain("Currently configured skills", prompt);
+        Assert.DoesNotContain("Currently configured agents", prompt);
+    }
+
+    [Fact]
+    public void BuildPrompt_SkillWithEmptyDescription_OmitsDescription()
+    {
+        var skills = new List<(string Name, string Description)>
+        {
+            ("deploy", "")
+        };
+
+        var prompt = InstructionRecommendationHelper.BuildRecommendationPrompt(
+            "/project", existingSkills: skills);
+
+        Assert.Contains("**deploy**", prompt);
+        // Should not have ": " after the name when description is empty
+        Assert.DoesNotContain("**deploy**: ", prompt);
+    }
+
+    [Fact]
+    public void BuildPrompt_AllParameters_IncludesEverything()
+    {
+        var skills = new List<(string Name, string Description)> { ("build", "Build it") };
+        var agents = new List<(string Name, string Description)> { ("review", "Review code") };
+
+        var prompt = InstructionRecommendationHelper.BuildRecommendationPrompt(
+            "/home/user/repo",
+            existingSkills: skills,
+            existingAgents: agents,
+            repoName: "org/repo");
+
+        Assert.Contains("org/repo", prompt);
+        Assert.Contains("/home/user/repo", prompt);
+        Assert.Contains("Currently configured skills", prompt);
+        Assert.Contains("Currently configured agents", prompt);
+        Assert.Contains("file path", prompt);
+    }
+}
diff --git a/PolyPilot.Tests/PolyPilot.Tests.csproj b/PolyPilot.Tests/PolyPilot.Tests.csproj
index b8285fb8..ae0cd8d3 100644
--- a/PolyPilot.Tests/PolyPilot.Tests.csproj
+++ b/PolyPilot.Tests/PolyPilot.Tests.csproj
@@ -29,6 +29,7 @@
     <Compile Include="../PolyPilot/Models/FiestaModels.cs" Link="Shared/FiestaModels.cs" />
     <Compile Include="../PolyPilot/Models/ModelHelper.cs" Link="Shared/ModelHelper.cs" />
     <Compile Include="../PolyPilot/Services/NotificationMessageBuilder.cs" Link="Shared/NotificationMessageBuilder.cs" />
+    <Compile Include="../PolyPilot/Models/InstructionRecommendationHelper.cs" Link="Shared/InstructionRecommendationHelper.cs" />
   </ItemGroup>
 
 </Project>
diff --git a/PolyPilot/Components/Layout/SessionListItem.razor b/PolyPilot/Components/Layout/SessionListItem.razor
index fa453704..630ccaf3 100644
--- a/PolyPilot/Components/Layout/SessionListItem.razor
+++ b/PolyPilot/Components/Layout/SessionListItem.razor
@@ -114,6 +114,10 @@
                     </button>
                     <div class="menu-separator"></div>
                 }
+                <button class="menu-item" @onclick="() => { OnCloseMenu.InvokeAsync(); OnRecommendInstructions.InvokeAsync(); }">
+                    💡 Recommend Instructions
+                </button>
+                <div class="menu-separator"></div>
                 <button class="menu-item destructive" @onclick="() => { OnCloseMenu.InvokeAsync(); OnClose.InvokeAsync(); }">
                     🗑 Close Session
                 </button>
@@ -141,6 +145,7 @@
     [Parameter] public EventCallback OnCommitRename { get; set; }
     [Parameter] public EventCallback OnToggleMenu { get; set; }
     [Parameter] public EventCallback OnCloseMenu { get; set; }
+    [Parameter] public EventCallback OnRecommendInstructions { get; set; }
 
     private async Task HandleRenameKeyDown(KeyboardEventArgs e)
     {
diff --git a/PolyPilot/Components/Layout/SessionSidebar.razor b/PolyPilot/Components/Layout/SessionSidebar.razor
index 4e75a5ce..4ea8bc72 100644
--- a/PolyPilot/Components/Layout/SessionSidebar.razor
+++ b/PolyPilot/Components/Layout/SessionSidebar.razor
@@ -244,6 +244,9 @@ else
                                                     <button class="group-menu-item" @onclick="() => { openGroupMenuId = null; createSessionFormRef?.ExpandForRepo(rId); }">
                                                         ➕ New Session
                                                     </button>
+                                                    <button class="group-menu-item" @onclick="() => { openGroupMenuId = null; CopilotService.RequestInstructionRecommendation(repoId: rId); }">
+                                                        💡 Recommend Instructions
+                                                    </button>
                                                     <div class="group-menu-separator"></div>
                                                     <button class="group-menu-item destructive" @onclick="() => { openGroupMenuId = null; confirmRemoveRepoId = rId; }">
                                                         🗑 Remove Repo
@@ -287,7 +290,8 @@ else
                                              OnStartRename="() => StartRename(sName)"
                                              OnCommitRename="CommitRename"
                                              OnToggleMenu="() => ToggleSessionMenu(sName)"
-                                             OnCloseMenu="() => { openMenuSession = null; }" />
+                                             OnCloseMenu="() => { openMenuSession = null; }"
+                                             OnRecommendInstructions="() => CopilotService.RequestInstructionRecommendation(sName)" />
                         }
                     }
                 }
diff --git a/PolyPilot/Components/Pages/Dashboard.razor b/PolyPilot/Components/Pages/Dashboard.razor
index 1396878a..28c40130 100644
--- a/PolyPilot/Components/Pages/Dashboard.razor
+++ b/PolyPilot/Components/Pages/Dashboard.razor
@@ -10,6 +10,7 @@
 @inject GitAutoUpdateService GitAutoUpdate
 @inject QrScannerService QrScanner
 @inject FiestaService FiestaService
+@inject RepoManager RepoManager
 @implements IAsyncDisposable
 
 <div class="dashboard @(expandedSession != null ? "expanded-mode" : "")">
@@ -259,6 +260,7 @@
         CopilotService.OnError += HandleError;
         CopilotService.OnTurnStart += HandleTurnStart;
         CopilotService.OnTurnEnd += HandleTurnEnd;
+        CopilotService.OnInstructionRecommendationRequested += HandleInstructionRecommendation;
         FiestaService.OnStateChanged += HandleFiestaStateChanged;
         FiestaService.OnHostTaskUpdate += HandleFiestaTaskUpdate;
 
@@ -1102,6 +1104,7 @@
                     "- `/status` — Show git status\n" +
                     "- `/mcp` — List MCP servers (enable/disable with `/mcp enable|disable <name>`)\n" +
                     "- `/plugin` — List installed plugins (enable/disable with `/plugin enable|disable <name>`)\n" +
+                    "- `/instructions` — Recommend instruction, skill, and agent improvements\n" +
                     "- `!<command>` — Run a shell command"));
                 break;
 
@@ -1222,6 +1225,10 @@
                 HandlePluginCommand(session, arg);
                 break;
 
+            case "instructions":
+                await SendInstructionRecommendation(sessionName, null);
+                return;
+
             default:
                 // Unknown command — pass through to the SDK as a regular prompt
                 _ = CopilotService.SendPromptAsync(sessionName, input);
@@ -1234,6 +1241,77 @@
         await InvokeAsync(SafeRefreshAsync);
     }
 
+    private void HandleInstructionRecommendation(string? sessionName, string? repoId)
+    {
+        _ = InvokeAsync(async () =>
+        {
+            await SendInstructionRecommendation(sessionName, repoId);
+        });
+    }
+
+    private async Task SendInstructionRecommendation(string? sessionName, string? repoId)
+    {
+        // Resolve the target session
+        string targetSession;
+        if (!string.IsNullOrEmpty(sessionName) && sessions.Any(s => s.Name == sessionName))
+        {
+            targetSession = sessionName;
+        }
+        else if (!string.IsNullOrEmpty(expandedSession))
+        {
+            targetSession = expandedSession;
+        }
+        else if (sessions.Count > 0)
+        {
+            targetSession = sessions[0].Name;
+        }
+        else
+        {
+            return; // No session available
+        }
+
+        var session = sessions.FirstOrDefault(s => s.Name == targetSession);
+        if (session == null) return;
+
+        // Determine working directory and repo name
+        string? workingDirectory = session.WorkingDirectory;
+        string? repoName = null;
+
+        if (!string.IsNullOrEmpty(repoId))
+        {
+            var repo = RepoManager.Repositories.FirstOrDefault(r => r.Id == repoId);
+            if (repo != null)
+            {
+                repoName = repo.Name;
+                // Try to find a worktree for this repo to use as working directory
+                var worktree = RepoManager.Worktrees.FirstOrDefault(w => w.RepoId == repoId);
+                if (worktree != null && !string.IsNullOrEmpty(worktree.Path))
+                    workingDirectory = worktree.Path;
+            }
+        }
+
+        // Gather existing skills and agents
+        var skills = CopilotService.DiscoverAvailableSkills(workingDirectory)
+            .Select(s => (s.Name, s.Description)).ToList();
+        var agents = CopilotService.DiscoverAvailableAgents(workingDirectory)
+            .Select(a => (a.Name, a.Description)).ToList();
+
+        var prompt = InstructionRecommendationHelper.BuildRecommendationPrompt(
+            workingDirectory, skills, agents, repoName);
+
+        // Select and expand this session
+        CopilotService.SetActiveSession(targetSession);
+        expandedSession = targetSession;
+        _explicitlyCollapsed = false;
+
+        session.History.Add(ChatMessage.UserMessage("/instructions"));
+        session.MessageCount = session.History.Count;
+        _needsScrollToBottom = true;
+        await InvokeAsync(SafeRefreshAsync);
+
+        _ = CopilotService.SendPromptAsync(targetSession, prompt);
+    }
+
     private async Task RunGitCommand(string sessionName, AgentSessionInfo session, string gitArgs)
     {
         var cwd = GetShellCwd(sessionName);
@@ -2216,6 +2294,7 @@
         CopilotService.OnError -= HandleError;
         CopilotService.OnTurnStart -= HandleTurnStart;
         CopilotService.OnTurnEnd -= HandleTurnEnd;
+        CopilotService.OnInstructionRecommendationRequested -= HandleInstructionRecommendation;
         FiestaService.OnStateChanged -= HandleFiestaStateChanged;
         FiestaService.OnHostTaskUpdate -= HandleFiestaTaskUpdate;
         foreach (var images in pendingImagesBySession.Values)
diff --git a/PolyPilot/Models/InstructionRecommendationHelper.cs b/PolyPilot/Models/InstructionRecommendationHelper.cs
new file mode 100644
index 00000000..db729896
--- /dev/null
+++ b/PolyPilot/Models/InstructionRecommendationHelper.cs
@@ -0,0 +1,77 @@
+using System.Text;
+
+namespace PolyPilot.Models;
+
+/// <summary>
+/// Builds prompts for generating instruction recommendations (skills, agents, copilot-instructions).
+/// </summary>
+public static class InstructionRecommendationHelper
+{
+    /// <summary>
+    /// Build a recommendation prompt that asks the AI to analyze the project and suggest
+    /// improvements to skills, agents, and copilot instruction files.
+    /// </summary>
+    /// <param name="workingDirectory">The project directory to analyze (may be null).</param>
+    /// <param name="existingSkills">Currently discovered skills.</param>
+    /// <param name="existingAgents">Currently discovered agents.</param>
+    /// <param name="repoName">Optional repository display name.</param>
+    public static string BuildRecommendationPrompt(
+        string? workingDirectory,
+        IReadOnlyList<(string Name, string Description)>? existingSkills = null,
+        IReadOnlyList<(string Name, string Description)>? existingAgents = null,
+        string? repoName = null)
+    {
+        var sb = new StringBuilder();
+
+        sb.AppendLine("Analyze this project and recommend improvements to the AI coding assistant configuration.");
+        sb.AppendLine();
+
+        if (!string.IsNullOrEmpty(repoName))
+            sb.AppendLine($"**Repository:** {repoName}");
+        if (!string.IsNullOrEmpty(workingDirectory))
+            sb.AppendLine($"**Working directory:** {workingDirectory}");
+
+        sb.AppendLine();
+        sb.AppendLine("Please examine the project structure, code patterns, build system, and development workflow, then provide specific recommendations for:");
+        sb.AppendLine();
+        sb.AppendLine("1. **Copilot Instructions** (`.github/copilot-instructions.md`) — Suggest project-specific instructions that would help the AI understand conventions, architecture patterns, preferred libraries, naming conventions, error handling patterns, and other project-specific knowledge.");
+        sb.AppendLine();
+        sb.AppendLine("2. **Skills** (`.github/skills/` or `.copilot/skills/`) — Recommend reusable skills (with SKILL.md frontmatter) for common project tasks like building, testing, deploying, or domain-specific operations.");
+        sb.AppendLine();
+        sb.AppendLine("3. **Agents** (`.github/agents/` or `.copilot/agents/`) — Suggest specialized agent definitions for recurring workflows like code review, documentation generation, refactoring, or project-specific automation.");
+
+        if (existingSkills != null && existingSkills.Count > 0)
+        {
+            sb.AppendLine();
+            sb.AppendLine("**Currently configured skills:**");
+            foreach (var skill in existingSkills)
+            {
+                sb.Append($"- **{skill.Name}**");
+                if (!string.IsNullOrEmpty(skill.Description))
+                    sb.Append($": {skill.Description}");
+                sb.AppendLine();
+            }
+        }
+
+        if (existingAgents != null && existingAgents.Count > 0)
+        {
+            sb.AppendLine();
+            sb.AppendLine("**Currently configured agents:**");
+            foreach (var agent in existingAgents)
+            {
+                sb.Append($"- **{agent.Name}**");
+                if (!string.IsNullOrEmpty(agent.Description))
+                    sb.Append($": {agent.Description}");
+                sb.AppendLine();
+            }
+        }
+
+        sb.AppendLine();
+        sb.AppendLine("For each recommendation, provide:");
+        sb.AppendLine("- The file path where it should be created or updated");
+        sb.AppendLine("- The complete content to add");
+        sb.AppendLine("- A brief explanation of why it would be valuable");
+
+        return sb.ToString();
+    }
+}
diff --git a/PolyPilot/Services/CopilotService.cs b/PolyPilot/Services/CopilotService.cs
index 79d9a05c..b3ff0b70 100644
--- a/PolyPilot/Services/CopilotService.cs
+++ b/PolyPilot/Services/CopilotService.cs
@@ -172,6 +172,16 @@ public CopilotService(ChatDatabase chatDb, ServerManager serverManager, WsBridge
     public event Action<string, SessionUsageInfo>? OnUsageInfoChanged; // sessionName, usageInfo
     public event Action<string>? OnTurnStart; // sessionName
     public event Action<string>? OnTurnEnd; // sessionName
+    public event Action<string?, string?>? OnInstructionRecommendationRequested; // sessionName, repoId
+
+    /// <summary>
+    /// Request instruction recommendations for a session or repository.
+    /// Fires OnInstructionRecommendationRequested so the Dashboard can handle it.
+    /// </summary>
+    public void RequestInstructionRecommendation(string? sessionName = null, string? repoId = null)
+    {
+        OnInstructionRecommendationRequested?.Invoke(sessionName, repoId);
+    }
 
     private class SessionState
     {