#Requires -Version 5.1
<#
    JbTecWiz Support Centre -- generated fix script

    Fault : Outlook keeps asking for a password and will not accept it
    Fix   : Clear the stored credentials in the right order
    Source: https://jbtecwiz.com/support/win-app-outlook-password

    Run as     : PowerShell as the affected user, with Outlook closed
    Expect     : 20 minutes
    Risk       : low
    Reversible : yes

    WHEN THIS IS THE RIGHT FIX
    Always start here. Clearing one store and not the others is why this
    fault appears to come back.

    HOW TO UNDO IT
    Credentials are re-created on the next successful sign-in; nothing is
    lost.

    This script walks the fix one step at a time and asks before each
    one. Steps with no command are things you do yourself -- it prints
    those and waits. Run with -DryRun to print without executing.

    --------------------------------------------------------------------
    NO WARRANTY - USE AT YOUR OWN RISK

    This script is provided by JbTecWiz as-is and with no warranty of any
    kind, express or implied. You run it entirely at your own risk.

    JbTecWiz accepts no liability for any loss or damage arising from its
    use, including but not limited to data loss, downtime, or configuration
    changes that turn out to be wrong for your system.

    You are responsible for reading this script before running it, for
    satisfying yourself that it suits the machine in front of you, and for
    having a working backup first. Some steps cannot be undone.
    --------------------------------------------------------------------
#>

[CmdletBinding()]
param(
    # Print every step and command without running anything.
    [switch]$DryRun,
    # Do not ask before each step. Read the script first if you use this.
    [switch]$Unattended
)

$ErrorActionPreference = 'Stop'
$script:Failed = 0

function Write-Rule { param([string]$Text)
    Write-Host ''
    Write-Host ('-' * 70) -ForegroundColor DarkGray
    if ($Text) { Write-Host $Text -ForegroundColor Cyan }
}

function Show-Prose { param([string]$Text, [string]$Colour = "Gray")
    if (-not $Text) { return }
    $words = $Text -split "\s+"; $line = "  "
    foreach ($w in $words) {
        if (($line.Length + $w.Length) -gt 74) { Write-Host $line -ForegroundColor $Colour; $line = "  " }
        $line += "$w "
    }
    if ($line.Trim()) { Write-Host $line -ForegroundColor $Colour }
}

function Invoke-Step {
    param(
        [int]$Number, [string]$Do, [string]$Why,
        [scriptblock]$Command, [switch]$Manual, [string]$Shell = "powershell"
    )
    Write-Rule "  Step $Number of 5"
    Show-Prose $Do "White"
    if ($Why) { Write-Host ""; Show-Prose $Why "DarkGray" }

    if ($Manual) {
        Write-Host ''
        Write-Host '  -> Do this yourself, then press Enter to carry on.' -ForegroundColor Yellow
        if (-not $Unattended -and -not $DryRun) { [void](Read-Host) }
        return
    }

    Write-Host ''
    foreach ($l in ($Command.ToString().Trim() -split "`n")) {
        Write-Host ("    " + $l.Trim()) -ForegroundColor Green
    }
    Write-Host ''

    if ($DryRun) { Write-Host "  (dry run -- not executed)" -ForegroundColor DarkGray; return }
    if (-not $Unattended) {
        $a = Read-Host "  Run this step? [Y]es / [S]kip / [Q]uit"
        if ($a -match "^[Qq]") { Write-Host "  Stopped at your request."; exit 0 }
        if ($a -match "^[Ss]") { Write-Host "  Skipped." -ForegroundColor DarkGray; return }
    }
    try { & $Command }
    catch {
        $script:Failed++
        Write-Host ("  Step $Number failed: " + $_.Exception.Message) -ForegroundColor Red
        Show-Prose "The rest of the fix may depend on this. Read the write-up before carrying on." "Red"
        if (-not $Unattended) {
            $c = Read-Host "  Carry on anyway? [y/N]"
            if ($c -notmatch "^[Yy]") { exit 1 }
        }
    }
}

Write-Rule
Write-Host '  Outlook keeps asking for a password and will not accept it' -ForegroundColor White
Write-Host '  Clear the stored credentials in the right order' -ForegroundColor Cyan
Write-Host ''
Write-Host '  Risk: low   Reversible   20 minutes'
Write-Host ''
Show-Prose 'No warranty. Use at your own risk - JbTecWiz accepts no liability. Read it before you run it, and have a backup.' 'DarkYellow'
Write-Rule

if (-not $Unattended -and -not $DryRun) {
    $go = Read-Host '  Ready? [y/N]'
    if ($go -notmatch "^[Yy]") { Write-Host "  Nothing was changed."; exit 0 }
}

Invoke-Step -Number 1 -Do 'Close Outlook and Teams completely -- check Task Manager, because both leave background processes that hold the tokens.' -Command {
    Get-Process OUTLOOK,ms-teams,Teams -ErrorAction SilentlyContinue | Stop-Process -Force
}

Invoke-Step -Number 2 -Do 'List the Office-related credentials before removing them.' -Command {
    cmdkey /list | Select-String -Pattern 'MicrosoftOffice|MS.Outlook|SSO_POP|OneDrive'
}

Invoke-Step -Number 3 -Do 'Remove the Office entries.' -Why 'These are the entries Outlook consults before it prompts. Leaving one behind means the prompt you fill in is discarded in favour of the stale entry, which is precisely the loop being reported.' -Command {
    cmdkey /list | ForEach-Object {
      if ($_ -match 'Target:\s*(MicrosoftOffice\S+|MS\.Outlook\S+|SSO_POP\S+)') { cmdkey /delete:$($Matches[1]) }
    }
}

Invoke-Step -Number 4 -Do 'Open Outlook. It should prompt once and then stay signed in.' -Manual

Invoke-Step -Number 5 -Do 'If the prompt returns, sign out of Office entirely from File -> Office Account -> Sign out, restart, and sign back in.' -Manual

Write-Rule "  Confirm it worked"
Show-Prose 'Outlook connects and the status bar reads Connected. Restart the machine and confirm it does not prompt again.' 'White'
Write-Host ''
if (-not $DryRun) {
    cmdkey /list | Select-String -Pattern 'MicrosoftOffice'
}

Write-Rule
if ($script:Failed -gt 0) {
    Write-Host ("  Finished with " + $script:Failed + " failed step(s).") -ForegroundColor Yellow
    Show-Prose 'Read the full write-up at https://jbtecwiz.com/support/win-app-outlook-password' 'Yellow'
} else {
    Write-Host '  Finished.' -ForegroundColor Green
}
Write-Host ''
Show-Prose 'To undo: Credentials are re-created on the next successful sign-in; nothing is lost.' 'DarkGray'
Write-Rule