diff --git a/packages/coding-agent/CHANGELOG.md b/packages/coding-agent/CHANGELOG.md
index e772b3b0..0440adcf 100644
--- a/packages/coding-agent/CHANGELOG.md
+++ b/packages/coding-agent/CHANGELOG.md
@@ -6,6 +6,7 @@
 
 - Fixed Windows npm self-updates to move loaded native dependency packages out of the active install before reinstalling pi ([#4157](https://github.com/earendil-works/pi/issues/4157)).
 - Fixed `pi update --self` detection for pnpm v11 global installs whose package path resolves through the pnpm store ([#4647](https://github.com/earendil-works/pi/issues/4647)).
+- Fixed Windows pnpm self-updates to resolve pnpm command shims and run through pnpm instead of requiring manual updates ([#4157](https://github.com/earendil-works/pi/issues/4157)).
 
 ## [0.75.1] - 2026-05-18
 
diff --git a/packages/coding-agent/src/package-manager-cli.ts b/packages/coding-agent/src/package-manager-cli.ts
index a3ef1e21..d1a51e3b 100644
--- a/packages/coding-agent/src/package-manager-cli.ts
+++ b/packages/coding-agent/src/package-manager-cli.ts
@@ -506,8 +506,10 @@ export async function handlePackageCommand(args: string[]): Promise<boolean> {
 						return true;
 					}
 					const installMethod = detectInstallMethod();
-					if (process.platform === "win32" && installMethod !== "npm") {
-						console.error(chalk.red(`${APP_NAME} self-update on Windows is only supported for npm installs.`));
+					if (process.platform === "win32" && installMethod !== "npm" && installMethod !== "pnpm") {
+						console.error(
+							chalk.red(`${APP_NAME} self-update on Windows is only supported for npm and pnpm installs.`),
+						);
 						console.error(chalk.dim(`Detected install method: ${installMethod}. Update ${APP_NAME} manually.`));
 						process.exitCode = 1;
 						return true;
@@ -523,7 +525,9 @@ export async function handlePackageCommand(args: string[]): Promise<boolean> {
 						return true;
 					}
 					try {
-						prepareWindowsNpmSelfUpdate();
+						if (installMethod === "npm") {
+							prepareWindowsNpmSelfUpdate();
+						}
 						await runSelfUpdate(selfUpdateCommand);
 					} catch (error: unknown) {
 						const message = error instanceof Error ? error.message : "Unknown package command error";
diff --git a/packages/coding-agent/src/utils/child-process.ts b/packages/coding-agent/src/utils/child-process.ts
index 73fdf5af..57ebd3ae 100644
--- a/packages/coding-agent/src/utils/child-process.ts
+++ b/packages/coding-agent/src/utils/child-process.ts
@@ -3,9 +3,9 @@ import { existsSync, readFileSync } from "node:fs";
 import { dirname, extname, join, resolve, sep } from "node:path";
 
 const EXIT_STDIO_GRACE_MS = 100;
-const WINDOWS_COMMAND_EXTENSIONS = ["", ".exe", ".cmd", ".bat"];
+const WINDOWS_COMMAND_EXTENSIONS = [".exe", ".cmd", ".bat", ""];
 const WINDOWS_COMMAND_SHIM_RE = /\.(?:cmd|bat)$/i;
-const NODE_SHIM_SCRIPT_RE = /(?:%~dp0|%dp0%|%basedir%)[^"'\r\n<>|&]*?\.(?:cjs|mjs|js)/i;
+const NODE_SHIM_SCRIPT_RE = /(?:%~dp0|%dp0%|%basedir%)[^"'\r\n<>|&]*?\.(?:cjs|mjs|js)/gi;
 
 export interface ResolvedSpawnCommand {
 	command: string;
@@ -45,10 +45,12 @@ function expandShimPath(path: string, shimPath: string): string {
 }
 
 function findNodeShimScript(shimPath: string): string | undefined {
-	const match = readFileSync(shimPath, "utf-8").match(NODE_SHIM_SCRIPT_RE);
-	if (!match) return undefined;
-	const scriptPath = expandShimPath(match[0], shimPath);
-	return existsSync(scriptPath) ? scriptPath : undefined;
+	const matches = [...readFileSync(shimPath, "utf-8").matchAll(NODE_SHIM_SCRIPT_RE)];
+	for (const match of matches.reverse()) {
+		const scriptPath = expandShimPath(match[0], shimPath);
+		if (existsSync(scriptPath)) return scriptPath;
+	}
+	return undefined;
 }
 
 export function resolveSpawnCommand(