Windows Dev Environment Weekly Maintenance — One Command for MSYS2 · winget · Toolchains

# MSYS2 (~700MB) — the build env's OS
winget install MSYS2.MSYS2
 
# pipx (Python global package manager)
python -m pip install --user pipx
python -m pipx ensurepath
 
# cargo-update extension
cargo install cargo-update
 
# Flutter (~1GB)
winget install Flutter.Flutter
# If not in winget: https://docs.flutter.dev/get-started/install/windows

<#
.SYNOPSIS
    Bulk system-tool update — Windows
.DESCRIPTION
    Refresh build env / package managers / language toolchains in one shot.
.NOTES
    Run: update-system.bat (admin recommended)
    Target: Windows 10/11
#>
 
$ErrorActionPreference = "Continue"
$script:Total = 8
$script:Step  = 0
 
function Step-Header {
    param([string]$Message)
    $script:Step++
    Write-Host ""
    Write-Host ("[{0}/{1}] {2}" -f $script:Step, $script:Total, $Message) -ForegroundColor Cyan
}
 
function Has-Command {
    param([string]$Cmd)
    $null = Get-Command $Cmd -ErrorAction SilentlyContinue
    return $?
}
 
function Write-OK   { param([string]$m) Write-Host "  OK   $m" -ForegroundColor Green }
function Write-Skip { param([string]$m) Write-Host "  SKIP $m" -ForegroundColor DarkGray }
function Write-Warn { param([string]$m) Write-Host "  WARN $m" -ForegroundColor Yellow }
function Write-Fail { param([string]$m) Write-Host "  FAIL $m" -ForegroundColor Red }
 
Write-Host "━━━ System update (Windows) ━━━" -ForegroundColor Cyan
 
# 1. MSYS2 (most important — OS of the build environment)
Step-Header "MSYS2 (pacman -Syuu) — critical"
$msys2Candidates = @(
    "C:\msys64\usr\bin\bash.exe",
    "D:\msys64\usr\bin\bash.exe",
    "C:\tools\msys64\usr\bin\bash.exe"
)
$msys2Bash = $msys2Candidates | Where-Object { Test-Path $_ } | Select-Object -First 1
if ($msys2Bash) {
    Write-Host "  → using: $msys2Bash" -ForegroundColor DarkGray
    & $msys2Bash -lc "pacman -Syuu --noconfirm"
    if ($LASTEXITCODE -eq 0) {
        Write-OK "pacman -Syuu done (rerun once if core packages updated)"
    } else {
        Write-Fail "pacman -Syuu (after core updates, restart shell + rerun)"
    }
} else {
    Write-Skip "MSYS2 not installed (checked: C:\msys64, D:\msys64, C:\tools\msys64)"
}
 
# 2. winget
Step-Header "winget (system packages)"
if (Has-Command winget) {
    winget upgrade --all --silent --accept-package-agreements --accept-source-agreements
    if ($LASTEXITCODE -eq 0) { Write-OK "winget upgrade --all" }
    else { Write-Fail "winget upgrade --all (some packages may need admin/interactive)" }
} else {
    Write-Skip "winget not installed"
}
 
# 3. Scoop (optional)
Step-Header "Scoop (if installed)"
if (Has-Command scoop) {
    scoop update
    scoop update *
    Write-OK "scoop update / update *"
} else {
    Write-Skip "scoop not installed"
}
 
# 4. npm globals
Step-Header "npm globals"
if (Has-Command npm) {
    npm update -g
    if ($LASTEXITCODE -eq 0) { Write-OK "npm update -g" } else { Write-Fail "npm update -g" }
} else {
    Write-Skip "npm not installed"
}
 
# 5. Rust toolchain
Step-Header "Rust toolchain (rustup)"
if (Has-Command rustup) {
    rustup update
    if ($LASTEXITCODE -eq 0) { Write-OK "rustup update" } else { Write-Fail "rustup update" }
} else {
    Write-Skip "rustup not installed"
}
 
# 6. Cargo binaries
Step-Header "Cargo binaries (cargo install-update -a)"
if (Has-Command cargo) {
    cargo install-update --version 2>$null | Out-Null
    if ($LASTEXITCODE -eq 0) {
        cargo install-update -a
        if ($LASTEXITCODE -eq 0) { Write-OK "cargo install-update -a" }
        else { Write-Fail "cargo install-update -a" }
    } else {
        Write-Warn "cargo-update missing (install: cargo install cargo-update)"
    }
} else {
    Write-Skip "cargo not installed"
}
 
# 7. pipx
Step-Header "pipx (Python global tools)"
if (Has-Command pipx) {
    pipx upgrade-all
    if ($LASTEXITCODE -eq 0) { Write-OK "pipx upgrade-all" } else { Write-Fail "pipx upgrade-all" }
} else {
    Write-Skip "pipx not installed"
}
 
# 8. Flutter SDK
Step-Header "Flutter SDK (flutter upgrade)"
if (Has-Command flutter) {
    flutter upgrade
    if ($LASTEXITCODE -eq 0) { Write-OK "flutter upgrade" } else { Write-Fail "flutter upgrade" }
} else {
    Write-Skip "flutter not installed"
}
 
Write-Host ""
Write-Host "━━━ Done ━━━" -ForegroundColor Cyan
Write-Host "Checks: winget upgrade  /  npm outdated -g  /  pacman -Qu (MSYS2)" -ForegroundColor DarkGray

@echo off
title System Update
 
echo ============================================
echo   System Update (Windows)
echo   MSYS2 + winget + npm + rustup + cargo + pipx
echo ============================================
echo.
 
powershell.exe -NoProfile -ExecutionPolicy Bypass -File "%~dp0update-system.ps1" %*
 
if %errorlevel% neq 0 (
    echo.
    echo [ERROR] Update failed. Check log above.
) else (
    echo.
    echo [DONE] System update complete.
)
 
pause

$action = New-ScheduledTaskAction -Execute "powershell.exe" `
    -Argument '-NoProfile -Command "[System.Reflection.Assembly]::LoadWithPartialName(\"System.Windows.Forms\"); [System.Windows.Forms.MessageBox]::Show(\"Weekly update-system reminder\", \"Dev Maintenance\")"'
 
$trigger = New-ScheduledTaskTrigger -Weekly -DaysOfWeek Friday -At 10:00am
 
Register-ScheduledTask -TaskName "Dev Update Reminder" `
    -Action $action -Trigger $trigger `
    -Description "Weekly reminder to run update-system"