diff --git a/algo.ps1 b/algo.ps1
index bb2736da..20fe84fd 100644
--- a/algo.ps1
+++ b/algo.ps1
@@ -4,46 +4,87 @@ param(
     [string[]]$Arguments
 )
 
-# Check if we're running in WSL
-function Test-WSL {
-    return $env:WSL_DISTRO_NAME -or $env:WSLENV -or (Get-Command wsl -ErrorAction SilentlyContinue)
+# Check if we're actually running inside WSL (not just if WSL is available)
+function Test-RunningInWSL {
+    # These environment variables are only set when running inside WSL
+    return $env:WSL_DISTRO_NAME -or $env:WSLENV
 }
 
 # Function to run Algo in WSL
 function Invoke-AlgoInWSL {
     param($Arguments)
     
-    Write-Host "NOTICE: Ansible requires a Unix-like environment."
+    Write-Host "NOTICE: Ansible requires a Unix-like environment and cannot run natively on Windows."
     Write-Host "Attempting to run Algo via Windows Subsystem for Linux (WSL)..."
     Write-Host ""
     
     if (-not (Get-Command wsl -ErrorAction SilentlyContinue)) {
-        Write-Host "ERROR: WSL is not installed or not available." -ForegroundColor Red
+        Write-Host "ERROR: WSL (Windows Subsystem for Linux) is not installed." -ForegroundColor Red
         Write-Host ""
-        Write-Host "To use Algo on Windows, you need WSL. Please:"
-        Write-Host "1. Install WSL: Run 'wsl --install -d Ubuntu-22.04' in PowerShell as Administrator"
-        Write-Host "2. Restart your computer when prompted"
-        Write-Host "3. Set up Ubuntu and try running this script again"
+        Write-Host "Algo requires WSL to run Ansible on Windows. To install WSL:" -ForegroundColor Yellow
         Write-Host ""
-        Write-Host "Alternatively, see: https://github.com/trailofbits/algo/blob/master/docs/deploy-from-windows.md"
+        Write-Host "  Step 1: Open PowerShell as Administrator and run:"
+        Write-Host "          wsl --install -d Ubuntu-22.04" -ForegroundColor Cyan
+        Write-Host "          (Note: 22.04 LTS recommended for WSL stability)" -ForegroundColor Gray
+        Write-Host ""
+        Write-Host "  Step 2: Restart your computer when prompted"
+        Write-Host ""
+        Write-Host "  Step 3: After restart, open Ubuntu from the Start menu"
+        Write-Host "          and complete the initial setup (create username/password)"
+        Write-Host ""
+        Write-Host "  Step 4: Run this script again: .\algo.ps1"
+        Write-Host ""
+        Write-Host "For detailed instructions, see:" -ForegroundColor Yellow
+        Write-Host "https://github.com/trailofbits/algo/blob/master/docs/deploy-from-windows.md"
         exit 1
     }
     
-    # Check if a default WSL distribution is set
+    # Check if any WSL distributions are installed and running
+    Write-Host "Checking for WSL Linux distributions..."
     $wslList = wsl -l -v 2>$null
     if ($LASTEXITCODE -ne 0) {
-        Write-Host "ERROR: No WSL distributions found." -ForegroundColor Red
-        Write-Host "Please install a Linux distribution: wsl --install -d Ubuntu-22.04"
+        Write-Host "ERROR: WSL is installed but no Linux distributions are available." -ForegroundColor Red
+        Write-Host ""
+        Write-Host "You need to install Ubuntu. Run this command as Administrator:" -ForegroundColor Yellow
+        Write-Host "  wsl --install -d Ubuntu-22.04" -ForegroundColor Cyan
+        Write-Host "          (Note: 22.04 LTS recommended for WSL stability)" -ForegroundColor Gray
+        Write-Host ""
+        Write-Host "Then restart your computer and try again."
         exit 1
     }
     
-    Write-Host "Running Algo in WSL..."
-    if ($Arguments.Count -gt 0 -and $Arguments[0] -eq "update-users") {
-        $remainingArgs = $Arguments[1..($Arguments.Count-1)] -join " "
-        wsl bash -c "cd /mnt/c/$(pwd | Split-Path -Leaf) && ./algo update-users $remainingArgs"
-    } else {
-        $allArgs = $Arguments -join " "
-        wsl bash -c "cd /mnt/c/$(pwd | Split-Path -Leaf) && ./algo $allArgs"
+    Write-Host "Successfully found WSL. Launching Algo..." -ForegroundColor Green
+    Write-Host ""
+    
+    # Get current directory name for WSL path mapping
+    $currentDir = Split-Path -Leaf (Get-Location)
+    
+    try {
+        if ($Arguments.Count -gt 0 -and $Arguments[0] -eq "update-users") {
+            $remainingArgs = $Arguments[1..($Arguments.Count-1)] -join " "
+            wsl bash -c "cd /mnt/c/$currentDir 2>/dev/null || (echo 'Error: Cannot access directory in WSL. Make sure you are running from a Windows drive (C:, D:, etc.)' && exit 1) && ./algo update-users $remainingArgs"
+        } else {
+            $allArgs = $Arguments -join " "
+            wsl bash -c "cd /mnt/c/$currentDir 2>/dev/null || (echo 'Error: Cannot access directory in WSL. Make sure you are running from a Windows drive (C:, D:, etc.)' && exit 1) && ./algo $allArgs"
+        }
+        
+        if ($LASTEXITCODE -ne 0) {
+            Write-Host ""
+            Write-Host "Algo finished with exit code: $LASTEXITCODE" -ForegroundColor Yellow
+            if ($LASTEXITCODE -eq 1) {
+                Write-Host "This may indicate a configuration issue or user cancellation."
+            }
+        }
+    } catch {
+        Write-Host ""
+        Write-Host "ERROR: Failed to run Algo in WSL." -ForegroundColor Red
+        Write-Host "Error details: $($_.Exception.Message)" -ForegroundColor Red
+        Write-Host ""
+        Write-Host "Troubleshooting:" -ForegroundColor Yellow
+        Write-Host "1. Make sure you're running from a Windows drive (C:, D:, etc.)"
+        Write-Host "2. Try opening Ubuntu directly and running: cd /mnt/c/$currentDir && ./algo"
+        Write-Host "3. See: https://github.com/trailofbits/algo/blob/master/docs/deploy-from-windows.md"
+        exit 1
     }
 }
 
@@ -115,22 +156,35 @@ function Update-PathEnvironment {
 
 # Main execution
 try {
-    # Check if we're in WSL already
-    if (Test-WSL) {
-        Write-Host "Running in WSL environment, using standard approach..."
-        # In WSL, we can use the normal Linux approach
+    # Check if we're actually running inside WSL
+    if (Test-RunningInWSL) {
+        Write-Host "Detected WSL environment. Running Algo using standard Unix approach..."
+        
+        # Verify bash is available (should be in WSL)
+        if (-not (Get-Command bash -ErrorAction SilentlyContinue)) {
+            Write-Host "ERROR: Running in WSL but bash is not available." -ForegroundColor Red
+            Write-Host "Your WSL installation may be incomplete. Try running:" -ForegroundColor Yellow
+            Write-Host "  wsl --shutdown" -ForegroundColor Cyan
+            Write-Host "  wsl" -ForegroundColor Cyan
+            exit 1
+        }
+        
+        # Run the standard Unix algo script
         & bash -c "./algo $($Arguments -join ' ')"
         exit $LASTEXITCODE
     }
     
-    # We're on native Windows - Ansible won't work directly
-    # Try to use WSL instead
+    # We're on native Windows - need to use WSL
     Invoke-AlgoInWSL $Arguments
     
 } catch {
-    Write-Host "Error: $($_.Exception.Message)" -ForegroundColor Red
-    $manualInstallUrl = "https://docs.astral.sh/uv/getting-started/installation/"
-    Write-Host "For manual installation: $manualInstallUrl"
-    Write-Host "For WSL setup: https://github.com/trailofbits/algo/blob/master/docs/deploy-from-windows.md"
+    Write-Host ""
+    Write-Host "UNEXPECTED ERROR:" -ForegroundColor Red
+    Write-Host $_.Exception.Message -ForegroundColor Red
+    Write-Host ""
+    Write-Host "If you continue to have issues:" -ForegroundColor Yellow
+    Write-Host "1. Ensure WSL is properly installed and Ubuntu is set up"
+    Write-Host "2. See troubleshooting guide: https://github.com/trailofbits/algo/blob/master/docs/deploy-from-windows.md"
+    Write-Host "3. Or use WSL directly: open Ubuntu and run './algo'"
     exit 1
 }
\ No newline at end of file