diff --git a/packages/core/src/core/prompts.test.ts b/packages/core/src/core/prompts.test.ts
index 039453ca12f..424da21b210 100644
--- a/packages/core/src/core/prompts.test.ts
+++ b/packages/core/src/core/prompts.test.ts
@@ -4,12 +4,13 @@
  * SPDX-License-Identifier: Apache-2.0
  */
 
-import { describe, it, expect, vi, beforeEach } from 'vitest';
+import { describe, it, expect, vi, beforeEach, afterEach } from 'vitest';
 import { getCoreSystemPrompt, resolvePathFromEnv } from './prompts.js';
 import { isGitRepository } from '../utils/gitUtils.js';
 import fs from 'node:fs';
 import os from 'node:os';
 import path from 'node:path';
+import process from 'node:process';
 import type { Config } from '../config/config.js';
 import { CodebaseInvestigatorAgent } from '../agents/codebase-investigator.js';
 import { GEMINI_DIR } from '../utils/paths.js';
@@ -52,10 +53,12 @@ vi.mock('../config/models.js', async (importOriginal) => {
 
 describe('Core System Prompt (prompts.ts)', () => {
   let mockConfig: Config;
+
   beforeEach(() => {
     vi.resetAllMocks();
     vi.stubEnv('GEMINI_SYSTEM_MD', undefined);
     vi.stubEnv('GEMINI_WRITE_SYSTEM_MD', undefined);
+    vi.spyOn(process, 'platform', 'get').mockReturnValue('linux');
     mockConfig = {
       getToolRegistry: vi.fn().mockReturnValue({
         getAllToolNames: vi.fn().mockReturnValue([]),
@@ -79,6 +82,30 @@ describe('Core System Prompt (prompts.ts)', () => {
     } as unknown as Config;
   });
 
+  afterEach(() => {
+    vi.restoreAllMocks();
+  });
+
+  it('should use Windows-specific commands when platform is win32', () => {
+    vi.spyOn(process, 'platform', 'get').mockReturnValue('win32');
+    vi.mocked(isGitRepository).mockReturnValue(true);
+    const prompt = getCoreSystemPrompt(mockConfig);
+    expect(prompt).toContain("'Select-String'");
+    expect(prompt).toContain("'Get-Content -Tail 10'");
+    expect(prompt).toContain("'Get-Content -TotalCount 10'");
+    expect(prompt).toContain('git status ; git diff HEAD ; git log -n 3');
+  });
+
+  it('should use Linux-specific commands when platform is linux', () => {
+    vi.spyOn(process, 'platform', 'get').mockReturnValue('linux');
+    vi.mocked(isGitRepository).mockReturnValue(true);
+    const prompt = getCoreSystemPrompt(mockConfig);
+    expect(prompt).toContain("'grep'");
+    expect(prompt).toContain("'tail'");
+    expect(prompt).toContain("'head'");
+    expect(prompt).toContain('git status && git diff HEAD && git log -n 3');
+  });
+
   it('should include available_skills when provided in config', () => {
     const skills = [
       {
diff --git a/packages/core/src/core/prompts.ts b/packages/core/src/core/prompts.ts
index 0aec32f155b..d5cd879e6ba 100644
--- a/packages/core/src/core/prompts.ts
+++ b/packages/core/src/core/prompts.ts
@@ -130,6 +130,12 @@ export function getCoreSystemPrompt(
 
   const interactiveMode = config.isInteractive();
 
+  const isWindows = process.platform === 'win32';
+  const commandSeparator = isWindows ? ';' : '&&';
+  const grepCommand = isWindows ? 'Select-String' : 'grep';
+  const tailCommand = isWindows ? 'Get-Content -Tail 10' : 'tail';
+  const headCommand = isWindows ? 'Get-Content -TotalCount 10' : 'head';
+
   const skills = config.getSkillManager().getSkills();
   let skillsPrompt = '';
   if (skills.length > 0) {
@@ -260,7 +266,7 @@ IT IS CRITICAL TO FOLLOW THESE GUIDELINES TO AVOID EXCESSIVE TOKEN CONSUMPTION.
 - If a command is expected to produce a lot of output, use quiet or silent flags where available and appropriate.
 - Always consider the trade-off between output verbosity and the need for information. If a command's full output is essential for understanding the result, avoid overly aggressive quieting that might obscure important details.
 - If a command does not have quiet/silent flags or for commands with potentially long output that may not be useful, redirect stdout and stderr to temp files in the project's temporary directory. For example: 'command > <temp_dir>/out.log 2> <temp_dir>/err.log'.
-- After the command runs, inspect the temp files (e.g. '<temp_dir>/out.log' and '<temp_dir>/err.log') using commands like 'grep', 'tail', 'head', ... (or platform equivalents). Remove the temp files when done.
+- After the command runs, inspect the temp files (e.g. '<temp_dir>/out.log' and '<temp_dir>/err.log') using commands like '${grepCommand}', '${tailCommand}', '${headCommand}', ... (or platform equivalents). Remove the temp files when done.
 `;
   }
   return '';
@@ -338,7 +344,7 @@ ${(function () {
   - \`git diff HEAD\` to review all changes (including unstaged changes) to tracked files in work tree since last commit.
     - \`git diff --staged\` to review only staged changes when a partial commit makes sense or was requested by the user.
   - \`git log -n 3\` to review recent commit messages and match their style (verbosity, formatting, signature line, etc.)
-- Combine shell commands whenever possible to save time/steps, e.g. \`git status && git diff HEAD && git log -n 3\`.
+- Combine shell commands whenever possible to save time/steps, e.g. \`git status ${commandSeparator} git diff HEAD ${commandSeparator} git log -n 3\`.
 - Always propose a draft commit message. Never just ask the user to give you the full commit message.
 - Prefer commit messages that are clear, concise, and focused more on "why" and less on "what".${
       interactiveMode