Proof of concept to avoid assertion roulette by composing the assertion results and throwing at the end so you always get complete information from your tests

compound-assertions.ps1

$script:scope = ""
$script:results = @{}

function Get-Scope () { $script:scope }

function Set-Scope ($Name) {
    $script:scope = $Name
}

function Add-Result ($Result, $Scope = (Get-Scope)) { 
    if ($script:results.ContainsKey($Scope))
    {
        $script:results[$scope] += $Result
    }
    else
    {
       $script:results[$scope] = @($Result)
    }
}

function Test-Result ($Scope) { 
    $script:results.ContainsKey($Scope)
}

function Get-Result ($Scope) { 
    $script:results[$Scope]
}

function test ($Name, $ScriptBlock) {
    Set-Scope $Name
    try 
    {
        &$ScriptBlock
        if ((Test-Result $Name))
        {
            $fails = (Get-Result $Name)
            $r = "Failed with $($Fails.count) errors:`n$( $fails-join "`n")"
            Write-error $r -ErrorAction 'stop'
        }
        Write-Host -ForegroundColor Green $Name
    }
    catch {
        Write-Host -ForegroundColor Red "$Name - $_" 
    }

    
}

$script:scope = "a"
$script:results = @{"a" = @()}

function Assert-LessThanDelayed ($Actual, $Expected) {
    if ($Expected -ge $Actual) {
        Add-Result "Expected $Actual to be less than $Expected"
    }
}


function Assert-EqualDelayed ($Actual, $Expected) {
    if ($Expected -ne $Actual) {
        Add-Result "Expected $Actual but got $Expected"
    }
}

test "test1" {
    Assert-EqualDelayed 1 1

    Assert-EqualDelayed 10 1
    Assert-EqualDelayed 11 1
    Assert-LessThanDelayed 10 11
}

test "test2" {
    Assert-EqualDelayed 1 1

    Assert-EqualDelayed 11 1
    Assert-LessThanDelayed 10 11
}