diff --git a/sidecar/src/Aryx.AgentHost/Contracts/ProtocolModels.cs b/sidecar/src/Aryx.AgentHost/Contracts/ProtocolModels.cs
index 2a1f6b2..3db3622 100644
--- a/sidecar/src/Aryx.AgentHost/Contracts/ProtocolModels.cs
+++ b/sidecar/src/Aryx.AgentHost/Contracts/ProtocolModels.cs
@@ -251,6 +251,31 @@ public sealed class AgentActivityEventDto : SidecarEventDto
     public string? ToolName { get; init; }
 }
 
+public sealed class PermissionDetailDto
+{
+    public string Kind { get; init; } = string.Empty;
+    public string? Intention { get; init; }
+    public string? Command { get; init; }
+    public string? Warning { get; init; }
+    public IReadOnlyList<string>? PossiblePaths { get; init; }
+    public IReadOnlyList<string>? PossibleUrls { get; init; }
+    public bool? HasWriteFileRedirection { get; init; }
+    public string? FileName { get; init; }
+    public string? Diff { get; init; }
+    public string? NewFileContents { get; init; }
+    public string? Path { get; init; }
+    public string? ServerName { get; init; }
+    public string? ToolTitle { get; init; }
+    public object? Args { get; init; }
+    public bool? ReadOnly { get; init; }
+    public string? Url { get; init; }
+    public string? Subject { get; init; }
+    public string? Fact { get; init; }
+    public string? Citations { get; init; }
+    public string? ToolDescription { get; init; }
+    public string? HookMessage { get; init; }
+}
+
 public sealed class ApprovalRequestedEventDto : SidecarEventDto
 {
     public string SessionId { get; init; } = string.Empty;
@@ -262,6 +287,7 @@ public sealed class ApprovalRequestedEventDto : SidecarEventDto
     public string? PermissionKind { get; init; }
     public string Title { get; init; } = string.Empty;
     public string? Detail { get; init; }
+    public PermissionDetailDto? PermissionDetail { get; init; }
 }
 
 public sealed class CommandErrorEventDto : SidecarEventDto
diff --git a/sidecar/src/Aryx.AgentHost/Services/CopilotApprovalCoordinator.cs b/sidecar/src/Aryx.AgentHost/Services/CopilotApprovalCoordinator.cs
index 15ff8a6..0c8d948 100644
--- a/sidecar/src/Aryx.AgentHost/Services/CopilotApprovalCoordinator.cs
+++ b/sidecar/src/Aryx.AgentHost/Services/CopilotApprovalCoordinator.cs
@@ -10,6 +10,14 @@ internal sealed class CopilotApprovalCoordinator
     private const string RejectedDecision = "rejected";
     private const string ToolCallApprovalKind = "tool-call";
     private const string WebFetchToolName = "web_fetch";
+    private const string ShellPermissionKind = "shell";
+    private const string WritePermissionKind = "write";
+    private const string ReadPermissionKind = "read";
+    private const string McpPermissionKind = "mcp";
+    private const string UrlPermissionKind = "url";
+    private const string MemoryPermissionKind = "memory";
+    private const string CustomToolPermissionKind = "custom-tool";
+    private const string HookPermissionKind = "hook";
 
     private readonly ConcurrentDictionary<string, PendingApprovalRequest> _pendingApprovals = new(StringComparer.Ordinal);
 
@@ -131,6 +139,77 @@ internal sealed class CopilotApprovalCoordinator
             PermissionKind = permissionKind,
             Title = title,
             Detail = detail,
+            PermissionDetail = BuildPermissionDetail(request),
+        };
+    }
+
+    internal static PermissionDetailDto BuildPermissionDetail(PermissionRequest request)
+    {
+        ArgumentNullException.ThrowIfNull(request);
+
+        return request switch
+        {
+            PermissionRequestShell shell => new PermissionDetailDto
+            {
+                Kind = ShellPermissionKind,
+                Intention = NormalizeOptionalString(shell.Intention),
+                Command = NormalizeOptionalString(shell.FullCommandText),
+                Warning = NormalizeOptionalString(shell.Warning),
+                PossiblePaths = NormalizeOptionalStringList(shell.PossiblePaths),
+                PossibleUrls = NormalizeOptionalStringList(shell.PossibleUrls.Select(static candidate => candidate.Url)),
+                HasWriteFileRedirection = shell.HasWriteFileRedirection,
+            },
+            PermissionRequestWrite write => new PermissionDetailDto
+            {
+                Kind = WritePermissionKind,
+                Intention = NormalizeOptionalString(write.Intention),
+                FileName = NormalizeOptionalString(write.FileName),
+                Diff = NormalizeOptionalString(write.Diff),
+                NewFileContents = NormalizeOptionalString(write.NewFileContents),
+            },
+            PermissionRequestRead read => new PermissionDetailDto
+            {
+                Kind = ReadPermissionKind,
+                Intention = NormalizeOptionalString(read.Intention),
+                Path = NormalizeOptionalString(read.Path),
+            },
+            PermissionRequestMcp mcp => new PermissionDetailDto
+            {
+                Kind = McpPermissionKind,
+                ServerName = NormalizeOptionalString(mcp.ServerName),
+                ToolTitle = NormalizeOptionalString(mcp.ToolTitle),
+                Args = mcp.Args,
+                ReadOnly = mcp.ReadOnly,
+            },
+            PermissionRequestUrl url => new PermissionDetailDto
+            {
+                Kind = UrlPermissionKind,
+                Intention = NormalizeOptionalString(url.Intention),
+                Url = NormalizeOptionalString(url.Url),
+            },
+            PermissionRequestMemory memory => new PermissionDetailDto
+            {
+                Kind = MemoryPermissionKind,
+                Subject = NormalizeOptionalString(memory.Subject),
+                Fact = NormalizeOptionalString(memory.Fact),
+                Citations = NormalizeOptionalString(memory.Citations),
+            },
+            PermissionRequestCustomTool customTool => new PermissionDetailDto
+            {
+                Kind = CustomToolPermissionKind,
+                ToolDescription = NormalizeOptionalString(customTool.ToolDescription),
+                Args = customTool.Args,
+            },
+            PermissionRequestHook hook => new PermissionDetailDto
+            {
+                Kind = HookPermissionKind,
+                Args = hook.ToolArgs,
+                HookMessage = NormalizeOptionalString(hook.HookMessage),
+            },
+            _ => new PermissionDetailDto
+            {
+                Kind = NormalizeOptionalString(request.Kind) ?? "unknown",
+            },
         };
     }
 
@@ -307,6 +386,17 @@ internal sealed class CopilotApprovalCoordinator
         return string.IsNullOrWhiteSpace(value) ? null : value.Trim();
     }
 
+    private static IReadOnlyList<string>? NormalizeOptionalStringList(IEnumerable<string?> values)
+    {
+        List<string> normalized = values
+            .Select(NormalizeOptionalString)
+            .Where(static value => value is not null)
+            .Cast<string>()
+            .ToList();
+
+        return normalized.Count > 0 ? normalized : null;
+    }
+
     private sealed record PendingApprovalRequest(
         string RequestId,
         string SessionId,
diff --git a/sidecar/tests/Aryx.AgentHost.Tests/CopilotWorkflowRunnerTests.cs b/sidecar/tests/Aryx.AgentHost.Tests/CopilotWorkflowRunnerTests.cs
index 5dfff93..0d41a4a 100644
--- a/sidecar/tests/Aryx.AgentHost.Tests/CopilotWorkflowRunnerTests.cs
+++ b/sidecar/tests/Aryx.AgentHost.Tests/CopilotWorkflowRunnerTests.cs
@@ -876,6 +876,9 @@ public sealed class CopilotWorkflowRunnerTests
         Assert.Equal("lsp_ts_hover", approvalEvent.ToolName);
         Assert.Equal("Approve lsp_ts_hover", approvalEvent.Title);
         Assert.Contains("tool \"lsp_ts_hover\"", approvalEvent.Detail);
+        Assert.NotNull(approvalEvent.PermissionDetail);
+        Assert.Equal("custom-tool", approvalEvent.PermissionDetail!.Kind);
+        Assert.Equal("Hover information", approvalEvent.PermissionDetail.ToolDescription);
     }
 
     [Fact]
@@ -907,6 +910,197 @@ public sealed class CopilotWorkflowRunnerTests
         Assert.Contains("url permission", approvalEvent.Detail);
         Assert.Contains("tool \"web_fetch\"", approvalEvent.Detail);
         Assert.Contains("https://example.com/docs", approvalEvent.Detail);
+        Assert.NotNull(approvalEvent.PermissionDetail);
+        Assert.Equal("url", approvalEvent.PermissionDetail!.Kind);
+        Assert.Equal("Fetch the requested page", approvalEvent.PermissionDetail.Intention);
+        Assert.Equal("https://example.com/docs", approvalEvent.PermissionDetail.Url);
+    }
+
+    [Fact]
+    public void BuildPermissionDetail_ExtractsShellRequestData()
+    {
+        PermissionDetailDto detail = CopilotApprovalCoordinator.BuildPermissionDetail(
+            new PermissionRequestShell
+            {
+                Kind = "shell",
+                ToolCallId = "tool-call-shell",
+                FullCommandText = "curl https://example.com/docs > docs.json",
+                Intention = "Fetch documentation with curl",
+                Commands =
+                [
+                    new PermissionRequestShellCommandsItem
+                    {
+                        Identifier = "curl",
+                        ReadOnly = true,
+                    },
+                ],
+                PossiblePaths = ["docs.json"],
+                PossibleUrls =
+                [
+                    new PermissionRequestShellPossibleUrlsItem
+                    {
+                        Url = "https://example.com/docs",
+                    },
+                ],
+                HasWriteFileRedirection = true,
+                CanOfferSessionApproval = false,
+                Warning = "Downloads remote content and writes it to disk.",
+            });
+
+        Assert.Equal("shell", detail.Kind);
+        Assert.Equal("curl https://example.com/docs > docs.json", detail.Command);
+        Assert.Equal("Fetch documentation with curl", detail.Intention);
+        Assert.Equal("Downloads remote content and writes it to disk.", detail.Warning);
+        Assert.Equal(["docs.json"], detail.PossiblePaths);
+        Assert.Equal(["https://example.com/docs"], detail.PossibleUrls);
+        Assert.True(detail.HasWriteFileRedirection);
+    }
+
+    [Fact]
+    public void BuildPermissionDetail_ExtractsWriteRequestData()
+    {
+        PermissionDetailDto detail = CopilotApprovalCoordinator.BuildPermissionDetail(
+            new PermissionRequestWrite
+            {
+                Kind = "write",
+                ToolCallId = "tool-call-write",
+                Intention = "Update README guidance",
+                FileName = "README.md",
+                Diff = "@@ -1 +1 @@\n-Hello\n+Hello world",
+                NewFileContents = "# README",
+            });
+
+        Assert.Equal("write", detail.Kind);
+        Assert.Equal("Update README guidance", detail.Intention);
+        Assert.Equal("README.md", detail.FileName);
+        Assert.Equal("@@ -1 +1 @@\n-Hello\n+Hello world", detail.Diff);
+        Assert.Equal("# README", detail.NewFileContents);
+    }
+
+    [Fact]
+    public void BuildPermissionDetail_ExtractsReadRequestData()
+    {
+        PermissionDetailDto detail = CopilotApprovalCoordinator.BuildPermissionDetail(
+            new PermissionRequestRead
+            {
+                Kind = "read",
+                ToolCallId = "tool-call-read",
+                Intention = "Inspect the README",
+                Path = "README.md",
+            });
+
+        Assert.Equal("read", detail.Kind);
+        Assert.Equal("Inspect the README", detail.Intention);
+        Assert.Equal("README.md", detail.Path);
+    }
+
+    [Fact]
+    public void BuildPermissionDetail_ExtractsMcpRequestData()
+    {
+        PermissionDetailDto detail = CopilotApprovalCoordinator.BuildPermissionDetail(
+            new PermissionRequestMcp
+            {
+                Kind = "mcp",
+                ToolCallId = "tool-call-mcp",
+                ServerName = "Git MCP",
+                ToolName = "git.status",
+                ToolTitle = "Git Status",
+                Args = new Dictionary<string, object?>
+                {
+                    ["path"] = ".",
+                },
+                ReadOnly = true,
+            });
+
+        Assert.Equal("mcp", detail.Kind);
+        Assert.Equal("Git MCP", detail.ServerName);
+        Assert.Equal("Git Status", detail.ToolTitle);
+        Assert.True(detail.ReadOnly);
+
+        Dictionary<string, object?> args = Assert.IsType<Dictionary<string, object?>>(detail.Args);
+        Assert.Equal(".", args["path"]);
+    }
+
+    [Fact]
+    public void BuildPermissionDetail_ExtractsUrlRequestData()
+    {
+        PermissionDetailDto detail = CopilotApprovalCoordinator.BuildPermissionDetail(
+            new PermissionRequestUrl
+            {
+                Kind = "url",
+                ToolCallId = "tool-call-url",
+                Intention = "Fetch the requested page",
+                Url = "https://example.com/docs",
+            });
+
+        Assert.Equal("url", detail.Kind);
+        Assert.Equal("Fetch the requested page", detail.Intention);
+        Assert.Equal("https://example.com/docs", detail.Url);
+    }
+
+    [Fact]
+    public void BuildPermissionDetail_ExtractsMemoryRequestData()
+    {
+        PermissionDetailDto detail = CopilotApprovalCoordinator.BuildPermissionDetail(
+            new PermissionRequestMemory
+            {
+                Kind = "memory",
+                ToolCallId = "tool-call-memory",
+                Subject = "repo conventions",
+                Fact = "Use Bun for script execution.",
+                Citations = "package.json",
+            });
+
+        Assert.Equal("memory", detail.Kind);
+        Assert.Equal("repo conventions", detail.Subject);
+        Assert.Equal("Use Bun for script execution.", detail.Fact);
+        Assert.Equal("package.json", detail.Citations);
+    }
+
+    [Fact]
+    public void BuildPermissionDetail_ExtractsCustomToolRequestData()
+    {
+        PermissionDetailDto detail = CopilotApprovalCoordinator.BuildPermissionDetail(
+            new PermissionRequestCustomTool
+            {
+                Kind = "custom tool",
+                ToolName = "lsp_ts_hover",
+                ToolDescription = "Hover information",
+                Args = new Dictionary<string, object?>
+                {
+                    ["file"] = "src/index.ts",
+                    ["line"] = 12,
+                },
+            });
+
+        Assert.Equal("custom-tool", detail.Kind);
+        Assert.Equal("Hover information", detail.ToolDescription);
+
+        Dictionary<string, object?> args = Assert.IsType<Dictionary<string, object?>>(detail.Args);
+        Assert.Equal("src/index.ts", args["file"]);
+        Assert.Equal(12, args["line"]);
+    }
+
+    [Fact]
+    public void BuildPermissionDetail_ExtractsHookRequestData()
+    {
+        PermissionDetailDto detail = CopilotApprovalCoordinator.BuildPermissionDetail(
+            new PermissionRequestHook
+            {
+                Kind = "hook",
+                ToolName = "web_fetch",
+                ToolArgs = new Dictionary<string, object?>
+                {
+                    ["url"] = "https://example.com",
+                },
+                HookMessage = "Review required before fetch",
+            });
+
+        Assert.Equal("hook", detail.Kind);
+        Assert.Equal("Review required before fetch", detail.HookMessage);
+
+        Dictionary<string, object?> args = Assert.IsType<Dictionary<string, object?>>(detail.Args);
+        Assert.Equal("https://example.com", args["url"]);
     }
 
     [Fact]
diff --git a/sidecar/tests/Aryx.AgentHost.Tests/SidecarProtocolHostTests.cs b/sidecar/tests/Aryx.AgentHost.Tests/SidecarProtocolHostTests.cs
index 3232df5..22aea7b 100644
--- a/sidecar/tests/Aryx.AgentHost.Tests/SidecarProtocolHostTests.cs
+++ b/sidecar/tests/Aryx.AgentHost.Tests/SidecarProtocolHostTests.cs
@@ -249,6 +249,13 @@ public sealed class SidecarProtocolHostTests
                     AgentName = "Primary",
                     PermissionKind = "tool access",
                     Title = "Approve tool access",
+                    PermissionDetail = new PermissionDetailDto
+                    {
+                        Kind = "shell",
+                        Command = "git status",
+                        Intention = "Inspect repository state",
+                        PossiblePaths = ["README.md"],
+                    },
                 });
 
                 return [];
@@ -284,6 +291,11 @@ public sealed class SidecarProtocolHostTests
                 Assert.Equal("approval-1", approvalEvent.GetProperty("approvalId").GetString());
                 Assert.Equal("tool-call", approvalEvent.GetProperty("approvalKind").GetString());
                 Assert.Equal("Approve tool access", approvalEvent.GetProperty("title").GetString());
+                JsonElement permissionDetail = approvalEvent.GetProperty("permissionDetail");
+                Assert.Equal("shell", permissionDetail.GetProperty("kind").GetString());
+                Assert.Equal("git status", permissionDetail.GetProperty("command").GetString());
+                Assert.Equal("Inspect repository state", permissionDetail.GetProperty("intention").GetString());
+                Assert.Equal("README.md", Assert.Single(permissionDetail.GetProperty("possiblePaths").EnumerateArray()).GetString());
             },
             completionEvent =>
             {