diff --git a/extensions/cli/src/stream/streamChatResponse.getAllTools.test.ts b/extensions/cli/src/stream/streamChatResponse.getAllTools.test.ts
index 800ae9aa960..b3f329ec341 100644
--- a/extensions/cli/src/stream/streamChatResponse.getAllTools.test.ts
+++ b/extensions/cli/src/stream/streamChatResponse.getAllTools.test.ts
@@ -47,7 +47,6 @@ describe("getRequestTools - Tool Filtering", () => {
     // Read-only tools should still be available
     expect(toolNames).toContain("Read");
     expect(toolNames).toContain("List");
-    expect(toolNames).toContain("Search");
     expect(toolNames).toContain("Fetch");
     expect(toolNames).toContain("Checklist");
 
@@ -130,7 +129,6 @@ describe("getRequestTools - Tool Filtering", () => {
     expect(toolNames).toContain("Bash");
     expect(toolNames).toContain("Write");
     expect(toolNames).toContain("List");
-    expect(toolNames).toContain("Search");
   });
 
   test("plan mode should override allow flags (regression test for GitHub Actions issue)", async () => {
@@ -158,6 +156,5 @@ describe("getRequestTools - Tool Filtering", () => {
     // Read-only tools should be available
     expect(toolNames).toContain("Read");
     expect(toolNames).toContain("List");
-    expect(toolNames).toContain("Search");
   });
 });
diff --git a/extensions/cli/src/tools/index.tsx b/extensions/cli/src/tools/index.tsx
index 2c27d84bc6d..95dfc60f69b 100644
--- a/extensions/cli/src/tools/index.tsx
+++ b/extensions/cli/src/tools/index.tsx
@@ -27,7 +27,7 @@ import { multiEditTool } from "./multiEdit.js";
 import { readFileTool } from "./readFile.js";
 import { reportFailureTool } from "./reportFailure.js";
 import { runTerminalCommandTool } from "./runTerminalCommand.js";
-import { searchCodeTool } from "./searchCode.js";
+import { checkIfRipgrepIsInstalled, searchCodeTool } from "./searchCode.js";
 import {
   type Tool,
   type ToolCall,
@@ -57,32 +57,29 @@ const BASE_BUILTIN_TOOLS: Tool[] = [
   readFileTool,
   writeFileTool,
   listFilesTool,
-  searchCodeTool,
   runTerminalCommandTool,
   fetchTool,
   writeChecklistTool,
-  reportFailureTool,
 ];
 
+const BUILTIN_SEARCH_TOOLS: Tool[] = [searchCodeTool];
+
 // Get all builtin tools including dynamic ones, with capability-based filtering
 export async function getAllAvailableTools(
   isHeadless: boolean,
 ): Promise<Tool[]> {
   const tools = [...BASE_BUILTIN_TOOLS];
 
-  // Filter out ReportFailure tool if no agent ID is present
+  const isRipgrepInstalled = await checkIfRipgrepIsInstalled();
+  if (isRipgrepInstalled) {
+    tools.push(...BUILTIN_SEARCH_TOOLS);
+  }
+
+  // Add ReportFailure tool if no agent ID is present
   // (it requires --id to function and will confuse the agent if unavailable)
   const agentId = getAgentIdFromArgs();
-  if (!agentId) {
-    const reportFailureIndex = tools.findIndex(
-      (t) => t.name === reportFailureTool.name,
-    );
-    if (reportFailureIndex !== -1) {
-      tools.splice(reportFailureIndex, 1);
-      logger.debug(
-        `Filtered out ${reportFailureTool.name} tool - no agent ID present (--id flag not provided)`,
-      );
-    }
+  if (agentId) {
+    tools.push(reportFailureTool);
   }
 
   // If model is capable, exclude editTool in favor of multiEditTool
diff --git a/extensions/cli/src/tools/searchCode.ts b/extensions/cli/src/tools/searchCode.ts
index af9e78756f3..cd4a1d77eef 100644
--- a/extensions/cli/src/tools/searchCode.ts
+++ b/extensions/cli/src/tools/searchCode.ts
@@ -12,6 +12,15 @@ const execPromise = util.promisify(child_process.exec);
 const DEFAULT_MAX_RESULTS = 100;
 const MAX_LINE_LENGTH = 1000;
 
+export async function checkIfRipgrepIsInstalled(): Promise<boolean> {
+  try {
+    await execPromise("rg --version");
+    return true;
+  } catch {
+    return false;
+  }
+}
+
 export const searchCodeTool: Tool = {
   name: "Search",
   displayName: "Search",