PowerShell Write-Output inside "if" does not output anything

You can achieve desired results by replacing Write-Output with Write-Host. This is suitable only if your main concern is to produce output in the console as Write-Host does not go to stdout stream.

You can read more about difference between the 2 cmdlets in this SO thread :Which should I use: "Write-Host", "Write-Output", or "[console]::WriteLine"?

PowerShell functions are not like their traditional language counterparts: they can output multiple things. When you're using Write-Output, you are sending things down the pipeline, so func1() will return both a String and a Boolean. If you try this:

$return_values = func1;
$return_values | Get-Member

You will see that you get both System.String and System.Boolean objects in $return_values. Indeed the 'return' statement is more like an 'exit' or 'break' in traditional languages: it marks an exit point, but the function will actually return with whatever was already outputted (+ the optional return argument).

The quick fix to the issue is to change Write-Output to Write-Host, though they do slightly different things.