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Wingman

Wingman is a free macOS application for creating bootable Windows 10 or 11 installer USB drives from an ISO.

Place
#25 of 38
Score
5.9
Wingman's website

What Wingman is

Wingman is a free macOS application for creating bootable Windows 10 or 11 installer USB drives from an ISO. This native SwiftUI app is distributed as a signed and notarized DMG and runs on Apple Silicon and Intel Macs with macOS 13 Ventura or later. It identifies the Windows release and editions in a selected ISO, then splits a standard install.wim into FAT32-compatible parts using a built-in Swift splitter. An optional Windows 11 setting bypasses TPM, Secure Boot, RAM, and CPU checks while leaving Setup interactive. You supply the ISO and an USB drive of at least 8 GB; creating the installer erases that drive. Consumer ISOs using solid-compressed install.esd are unsupported. The resulting USB boots PCs, not Windows installers on Macs. Wingman excludes internal disks, rechecks the target before erasing, and limits root privileges to partitioning and formatting.

Good

  • Native app for Apple Silicon and Intel Macs
  • Detects Windows releases and editions
  • Built-in FAT32 WIM splitting
  • Optional Windows 11 requirement bypass
  • External-drive safety checks

Watch out

  • Requires macOS 13 Ventura or later
  • Creating media erases the selected USB drive
  • Consumer install.esd ISOs are unsupported
  • Cannot boot Windows installation on a Mac

Who it suits

Wingman suits Mac users who need Windows 10 or 11 installation media for PCs. It is intended for systems meeting its macOS, ISO, and USB requirements.

Verdict

Wingman provides a focused way to create Windows installer USB media from macOS. Check the ISO format, USB capacity, and target computer before proceeding because the process erases the selected drive.

Plans and prices

From Wingman's own pricing page, checked 10 Oct 2026.

All about pricing
PlanPriceWhat it gives you
FreeFreemacOS 13+ · Windows 10/11 ISO with standard install.wim · USB drive 8 GB or larger

The facts

Each one read from Wingman's own pages, with the date it was checked.

What it does

Boot target
The resulting USB boots PCs; the maker states it cannot boot a Windows installer on an Apple Silicon or Intel Mac.checked 10 Oct 2026
ISO limitation
The ISO must contain a standard install.wim; consumer ISOs using solid-compressed install.esd are unsupported.checked 10 Oct 2026
License and warranty
The project is GPL-3.0 and is provided as is without warranty.checked 10 Oct 2026
Privilege design
Only disk partitioning and formatting run with root privileges; device enumeration, ISO mounting, copying, and WIM splitting run unprivileged.checked 10 Oct 2026
Purpose
Wingman creates bootable Windows 10 or 11 USB installers from an ISO on macOS.checked 10 Oct 2026
Safety controls
Wingman lists external removable drives and excludes the internal or startup disk, with the helper revalidating the target before erasing.checked 10 Oct 2026
USB requirement
A USB stick of at least 8 GB is required, and creating the installer erases the selected drive.checked 10 Oct 2026
WIM splitting
Its pure-Swift splitter divides install.wim into parts that fit FAT32, without external libraries or codecs.checked 10 Oct 2026

The company

Maker
The repository owner is Ross Duggan, who describes himself as a software developer from Dublin.checked 10 Oct 2026

Where it runs

Native app
It is a native SwiftUI app distributed as a signed and notarized DMG.checked 10 Oct 2026
Platform requirements
Wingman requires macOS 13 Ventura or later and runs on Apple Silicon and Intel Macs.checked 10 Oct 2026
Windows 11 option
An optional Windows 11 toggle bypasses TPM, Secure Boot, RAM, and CPU checks while leaving Setup interactive.checked 10 Oct 2026
Windows detection
Wingman identifies the Windows release and editions from the selected ISO.checked 10 Oct 2026
Windows media
Users provide their own Windows ISO; Wingman says it does not distribute, bundle, or host Microsoft software.checked 10 Oct 2026

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