diff --git a/apps/studio/package.json b/apps/studio/package.json
index 9299e1b3e2..0d1e84dccf 100644
--- a/apps/studio/package.json
+++ b/apps/studio/package.json
@@ -52,7 +52,6 @@
 		"strip-ansi": "^7.1.2",
 		"tar": "^7.5.16",
 		"tus-js-client": "^4.3.1",
-		"winreg": "1.2.4",
 		"yauzl": "^3.2.1",
 		"zod": "^4.0.0"
 	},
@@ -81,7 +80,6 @@
 		"@types/react-dom": "^19.2.3",
 		"@types/semver": "^7.7.1",
 		"@types/shell-quote": "^1.7.5",
-		"@types/winreg": "^1.2.36",
 		"@types/yauzl": "^2.10.3",
 		"@vitejs/plugin-react": "^6.0.2",
 		"@wordpress/components": "34.0.0",
diff --git a/apps/studio/src/modules/cli/lib/windows-installation-manager.ts b/apps/studio/src/modules/cli/lib/windows-installation-manager.ts
index e140cc8f18..b1fb02a627 100644
--- a/apps/studio/src/modules/cli/lib/windows-installation-manager.ts
+++ b/apps/studio/src/modules/cli/lib/windows-installation-manager.ts
@@ -1,10 +1,10 @@
 import { app, dialog } from 'electron';
 import { mkdir, rm, writeFile } from 'fs/promises';
+import { spawn } from 'node:child_process';
 import { existsSync } from 'node:fs';
 import path from 'path';
 import * as Sentry from '@sentry/electron/main';
 import { __ } from '@wordpress/i18n';
-import Registry from 'winreg'; // don't update winreg to 1.2.5 - https://github.com/fresc81/node-winreg/issues/65
 import { getMainWindow } from 'src/main-window';
 import { StudioCliInstallationManager } from 'src/modules/cli/lib/ipc-handlers';
 import { loadUserData, updateAppdata } from 'src/storage/user-data';
@@ -12,13 +12,6 @@ import { loadUserData, updateAppdata } from 'src/storage/user-data';
 // `STABLE_BIN_DIR_PATH` resolves to C:\Users\<USERNAME>\AppData\Local\studio\bin
 export const STABLE_BIN_DIR_PATH = path.resolve( path.dirname( app.getPath( 'exe' ) ), '../bin' );
 
-const PATH_KEY = 'Path';
-
-const currentUserRegistry = new Registry( {
-	hive: Registry.HKCU,
-	key: '\\Environment',
-} );
-
 export class WindowsCliInstallationManager implements StudioCliInstallationManager {
 	constructor() {
 		if ( process.platform !== 'win32' ) {
@@ -118,28 +111,46 @@ export class WindowsCliInstallationManager implements StudioCliInstallationManag
 		}
 	}
 
-	private getPathFromRegistry(): Promise< string > {
+	private runPowerShell( script: string ): Promise< string > {
 		return new Promise( ( resolve, reject ) => {
-			currentUserRegistry.get( PATH_KEY, ( error, item ) => {
-				if ( error ) {
-					return reject( error );
-				}
+			const child = spawn(
+				'powershell.exe',
+				[ '-NoProfile', '-NonInteractive', '-WindowStyle', 'Hidden', '-Command', script ],
+				{ windowsHide: true }
+			);
 
-				resolve( item?.value || '' );
+			let stdout = '';
+			child.stdout.on( 'data', ( chunk ) => {
+				stdout += chunk.toString();
 			} );
+			child.on( 'error', reject );
+			child.on( 'exit', ( code ) =>
+				code === 0
+					? resolve( stdout )
+					: reject( new Error( `PowerShell exited with code ${ code }` ) )
+			);
 		} );
 	}
 
-	private setPathInRegistry( updatedPath: string ): Promise< void > {
-		return new Promise( ( resolve, reject ) => {
-			currentUserRegistry.set( PATH_KEY, Registry.REG_EXPAND_SZ, updatedPath, ( error ) => {
-				if ( error ) {
-					return reject( error );
-				}
+	private async getPathFromRegistry(): Promise< string > {
+		// Read the raw, unexpanded value (DoNotExpandEnvironmentNames) so that any
+		// %VAR% entries survive a read/modify/write round-trip untouched.
+		const script = `
+$key = [Microsoft.Win32.Registry]::CurrentUser.OpenSubKey('Environment')
+if ($key) {
+	[Console]::Out.Write([string]$key.GetValue('Path', '', [Microsoft.Win32.RegistryValueOptions]::DoNotExpandEnvironmentNames))
+	$key.Close()
+}`;
+		return ( await this.runPowerShell( script ) ).trim();
+	}
 
-				resolve();
-			} );
-		} );
+	private async setPathInRegistry( updatedPath: string ): Promise< void > {
+		// SetEnvironmentVariable(..., 'User') also broadcasts WM_SETTINGCHANGE so
+		// open shells pick up the new PATH without a re-login.
+		const escaped = updatedPath.replace( /'/g, "''" );
+		await this.runPowerShell(
+			`[Environment]::SetEnvironmentVariable('PATH', '${ escaped }', 'User')`
+		);
 	}
 
 	private async isStudioCliDirInPath(): Promise< boolean > {
diff --git a/package-lock.json b/package-lock.json
index 8666bca93d..80ffac126c 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -543,7 +543,6 @@
 				"strip-ansi": "^7.1.2",
 				"tar": "^7.5.16",
 				"tus-js-client": "^4.3.1",
-				"winreg": "1.2.4",
 				"yauzl": "^3.2.1",
 				"zod": "^4.0.0"
 			},
@@ -572,7 +571,6 @@
 				"@types/react-dom": "^19.2.3",
 				"@types/semver": "^7.7.1",
 				"@types/shell-quote": "^1.7.5",
-				"@types/winreg": "^1.2.36",
 				"@types/yauzl": "^2.10.3",
 				"@vitejs/plugin-react": "^6.0.2",
 				"@wordpress/components": "34.0.0",
@@ -4979,9 +4977,6 @@
 			"cpu": [
 				"arm64"
 			],
-			"libc": [
-				"glibc"
-			],
 			"license": "MIT",
 			"optional": true,
 			"os": [
@@ -4998,9 +4993,6 @@
 			"cpu": [
 				"arm64"
 			],
-			"libc": [
-				"musl"
-			],
 			"license": "MIT",
 			"optional": true,
 			"os": [
@@ -5017,9 +5009,6 @@
 			"cpu": [
 				"riscv64"
 			],
-			"libc": [
-				"glibc"
-			],
 			"license": "MIT",
 			"optional": true,
 			"os": [
@@ -5036,9 +5025,6 @@
 			"cpu": [
 				"x64"
 			],
-			"libc": [
-				"glibc"
-			],
 			"license": "MIT",
 			"optional": true,
 			"os": [
@@ -5055,9 +5041,6 @@
 			"cpu": [
 				"x64"
 			],
-			"libc": [
-				"musl"
-			],
 			"license": "MIT",
 			"optional": true,
 			"os": [
@@ -13813,11 +13796,6 @@
 			"dev": true,
 			"license": "MIT"
 		},
-		"node_modules/@types/winreg": {
-			"version": "1.2.36",
-			"dev": true,
-			"license": "MIT"
-		},
 		"node_modules/@types/wrap-ansi": {
 			"version": "3.0.0",
 			"dev": true,
@@ -32575,10 +32553,6 @@
 				"url": "https://github.com/sponsors/sindresorhus"
 			}
 		},
-		"node_modules/winreg": {
-			"version": "1.2.4",
-			"license": "BSD-2-Clause"
-		},
 		"node_modules/word-wrap": {
 			"version": "1.2.5",
 			"license": "MIT",