diff --git a/web/backend/api/tools.go b/web/backend/api/tools.go
index 289ea5035..629d5f43d 100644
--- a/web/backend/api/tools.go
+++ b/web/backend/api/tools.go
@@ -193,6 +193,12 @@ var toolCatalog = []toolCatalogEntry{
 		Category:    "discovery",
 		ConfigKey:   "mcp.discovery.use_bm25",
 	},
+	{
+		Name:        "request_permission",
+		Description: "Request user permission for accessing paths outside workspace.",
+		Category:    "system",
+		ConfigKey:   "request_permission",
+	},
 }
 
 func (h *Handler) registerToolRoutes(mux *http.ServeMux) {
diff --git a/web/frontend/src/components/chat/assistant-message.tsx b/web/frontend/src/components/chat/assistant-message.tsx
index 07a3c0abc..4ca1167c7 100644
--- a/web/frontend/src/components/chat/assistant-message.tsx
+++ b/web/frontend/src/components/chat/assistant-message.tsx
@@ -23,6 +23,7 @@ import {
   type ChatAttachment,
   type ChatToolCall,
 } from "@/store/chat"
+import { CompactToolCall } from "@/components/chat/compact-tool-call"
 
 interface AssistantMessageProps {
   content: string
@@ -114,71 +115,17 @@ export function AssistantMessage({
             </div>
           )}
           {(!isCollapsedBlock || isExpanded) && isToolCalls && hasToolCalls && (
-            <div className="space-y-3 px-3 pt-0 pb-3">
+            <div className="px-3 pt-0 pb-2">
               {toolCalls.map((toolCall, index) => {
-                const explanation =
-                  toolCall.extraContent?.toolFeedbackExplanation?.trim() ?? ""
                 const toolName = toolCall.function?.name?.trim() ?? ""
-                const toolArguments = toolCall.function?.arguments?.trim() ?? ""
-                const hasFunctionSummary = toolName || toolArguments
-
-                if (!explanation && !hasFunctionSummary) {
-                  return null
-                }
-
+                const isRequestPermission = toolName === "request_permission"
+                
                 return (
-                  <div
+                  <CompactToolCall
                     key={toolCall.id ?? `${toolName}-${index}`}
-                    className={cn(
-                      "space-y-3",
-                      index > 0 && "border-border/20 border-t pt-3",
-                    )}
-                  >
-                    {explanation && (
-                      <div className="space-y-1.5">
-                        <div className="text-muted-foreground/55 text-[11px] font-medium tracking-wide uppercase">
-                          {t("chat.toolCallExplanationLabel")}
-                        </div>
-                        <div className="prose dark:prose-invert prose-p:my-1.5 prose-p:whitespace-pre-wrap max-w-none text-[13px] leading-relaxed [overflow-wrap:anywhere] break-words opacity-75">
-                          <ReactMarkdown
-                            remarkPlugins={[remarkGfm]}
-                            rehypePlugins={[
-                              rehypeRaw,
-                              rehypeSanitize,
-                              rehypeHighlight,
-                            ]}
-                          >
-                            {explanation}
-                          </ReactMarkdown>
-                        </div>
-                      </div>
-                    )}
-
-                    {hasFunctionSummary && (
-                      <div
-                        className={cn(
-                          "space-y-1.5",
-                          explanation && "border-border/20 border-t pt-3",
-                        )}
-                      >
-                        <div className="text-muted-foreground/55 text-[11px] font-medium tracking-wide uppercase">
-                          {t("chat.toolCallFunctionLabel")}
-                        </div>
-                        <div className="bg-background/55 border-border/25 space-y-2 rounded-lg border px-3 py-2.5">
-                          {toolName && (
-                            <div className="text-foreground/75 font-mono text-[12px] font-semibold">
-                              {toolName}
-                            </div>
-                          )}
-                          {toolArguments && (
-                            <pre className="text-muted-foreground/75 overflow-x-auto font-mono text-[12px] leading-relaxed break-words whitespace-pre-wrap">
-                              {toolArguments}
-                            </pre>
-                          )}
-                        </div>
-                      </div>
-                    )}
-                  </div>
+                    toolCall={toolCall}
+                    isRequestPermission={isRequestPermission}
+                  />
                 )
               })}
             </div>
diff --git a/web/frontend/src/components/chat/chat-page.tsx b/web/frontend/src/components/chat/chat-page.tsx
index aa479d776..3031e9c9e 100644
--- a/web/frontend/src/components/chat/chat-page.tsx
+++ b/web/frontend/src/components/chat/chat-page.tsx
@@ -369,18 +369,6 @@ export function ChatPage() {
             />
           )}
 
-          {permissionRequest && (
-            <div className="flex w-full">
-              <PermissionPrompt
-                toolName={permissionRequest.toolName}
-                path={permissionRequest.path}
-                originalCommand={permissionRequest.originalCommand}
-                onPermissionGranted={handlePermissionGranted}
-                onPermissionDenied={handlePermissionDenied}
-              />
-            </div>
-          )}
-
           {messages.map((msg) => {
             if (
               !showAssistantDetails &&
@@ -421,6 +409,18 @@ export function ChatPage() {
         onChange={handleImageSelection}
       />
 
+      {permissionRequest && (
+        <div className="px-4 pb-2">
+          <PermissionPrompt
+            toolName={permissionRequest.toolName}
+            path={permissionRequest.path}
+            originalCommand={permissionRequest.originalCommand}
+            onPermissionGranted={handlePermissionGranted}
+            onPermissionDenied={handlePermissionDenied}
+          />
+        </div>
+      )}
+
       <ChatComposer
         input={input}
         attachments={attachments}
diff --git a/web/frontend/src/components/chat/compact-tool-call.tsx b/web/frontend/src/components/chat/compact-tool-call.tsx
new file mode 100644
index 000000000..3628bc177
--- /dev/null
+++ b/web/frontend/src/components/chat/compact-tool-call.tsx
@@ -0,0 +1,88 @@
+import { useState } from "react"
+
+import type { ChatToolCall } from "@/store/chat"
+
+interface CompactToolCallProps {
+  toolCall: ChatToolCall
+  isRequestPermission?: boolean
+}
+
+export function CompactToolCall({
+  toolCall,
+  isRequestPermission = false,
+}: CompactToolCallProps) {
+  const [isExpanded, setIsExpanded] = useState(isRequestPermission)
+  const toolName = toolCall.function?.name?.trim() ?? ""
+  const toolArguments = toolCall.function?.arguments?.trim() ?? ""
+  const explanation =
+    toolCall.extraContent?.toolFeedbackExplanation?.trim() ?? ""
+
+  // Try to parse args for display
+  let parsedArgs: Record<string, unknown> | null = null
+  if (toolArguments) {
+    try {
+      parsedArgs = JSON.parse(toolArguments)
+    } catch {
+      // ignore
+    }
+  }
+
+  // Status icon
+  const isError = explanation.toLowerCase().includes("error") || explanation.toLowerCase().includes("denied")
+
+  return (
+    <div
+      className={`flex items-start gap-2 py-1.5 text-[13px] border-b border-border/20 last:border-0 ${
+        isRequestPermission ? "bg-yellow-500/5 -mx-2 px-2 rounded-md" : ""
+      }`}
+    >
+      <button
+        onClick={() => setIsExpanded(!isExpanded)}
+        className="flex items-center gap-1.5 flex-1 text-left hover:opacity-80 transition-opacity"
+      >
+        <div
+          className={`flex items-center justify-center w-5 h-5 rounded shrink-0 mt-0.5 text-xs ${
+            isRequestPermission
+              ? "bg-yellow-500/20 text-yellow-600"
+              : isError
+                ? "bg-red-500/20 text-red-600"
+                : "bg-green-500/20 text-green-600"
+          }`}
+        >
+          {isExpanded ? "▼" : "🔧"}
+        </div>
+        <span className="font-medium text-foreground/90">{toolName}</span>
+        {!isExpanded && parsedArgs && (
+          <span className="text-muted-foreground/70 truncate">
+            {String(parsedArgs.path ?? parsedArgs.command ?? "")}
+          </span>
+        )}
+        {!isExpanded && !parsedArgs && explanation && (
+          <span className="text-muted-foreground/70 truncate max-w-[200px]">
+            {explanation}
+          </span>
+        )}
+        {!isExpanded && (
+          <span className={`shrink-0 ml-auto text-xs ${isError ? "text-red-500" : "text-green-500"}`}>
+            {isError ? "✗" : "✓"}
+          </span>
+        )}
+      </button>
+
+      {isExpanded && (explanation || toolArguments) && (
+        <div className="mt-1 space-y-2 w-full">
+          {explanation && (
+            <div className="text-muted-foreground/80 text-[12px] leading-relaxed whitespace-pre-wrap">
+              {explanation}
+            </div>
+          )}
+          {toolArguments && (
+            <div className="bg-muted/30 rounded-md p-2 font-mono text-[11px] overflow-x-auto">
+              <pre className="whitespace-pre-wrap break-all">{toolArguments}</pre>
+            </div>
+          )}
+        </div>
+      )}
+    </div>
+  )
+}