Script for sending email doesn't work with Gmail account

Question

here there is a simple script to send an email.

If I run it using Gmail settings (ie smtp.gmail.com on port 465 or 587) the script doesn't work returning the error

Server error response: 5.7.0 Authentication Required

# graphical stuff
Add-Type -AssemblyName System.Windows.Forms
Add-Type -AssemblyName System.Drawing
Add-Type -AssemblyName PresentationFramework

# import modules
$workdir = Get-Location
Import-Module -Name "$workdir\Modules\Forms.psm1" # module for windows forms

$answ = [System.Windows.MessageBox]::Show("Configure for sending mail alerts?",'ALERTS','YesNo','Info')
if ($answ -eq "Yes") {    
    # dialog box
    $formail = New-Object System.Windows.Forms.Form
    $formail.Text = "CONFIG"
    $formail.Size = "500,300"
    $formail.StartPosition = 'CenterScreen'
    $formail.Topmost = $true
    $address = New-Object System.Windows.Forms.Label
    $address.Location = New-Object System.Drawing.Size(10,20) 
    $address.Size = New-Object System.Drawing.Size(120,20) 
    $address.Text = "Mail address:"
    $formail.Controls.Add($address)
    $addressbox = New-Object System.Windows.Forms.TextBox
    $addressbox.Location = New-Object System.Drawing.Point(130,20)
    $addressbox.Size = New-Object System.Drawing.Size(300,20)
    $formail.Add_Shown({$addressbox.Select()})
    $formail.Controls.Add($addressbox)
    $passwd = New-Object System.Windows.Forms.Label
    $passwd.Location = New-Object System.Drawing.Size(10,50) 
    $passwd.Size = New-Object System.Drawing.Size(120,20) 
    $passwd.Text = "Password:"
    $formail.Controls.Add($passwd)
    $passwdbox = New-Object System.Windows.Forms.MaskedTextBox
    $passwdbox.PasswordChar = '*'
    $passwdbox.Location = New-Object System.Drawing.Point(130,50)
    $passwdbox.Size = New-Object System.Drawing.Size(300,20)
    $formail.Add_Shown({$passwdbox.Select()})
    $formail.Controls.Add($passwdbox)
    $smtp = New-Object System.Windows.Forms.Label
    $smtp.Location = New-Object System.Drawing.Size(10,80) 
    $smtp.Size = New-Object System.Drawing.Size(120,20) 
    $smtp.Text = "SMTP server:"
    $formail.Controls.Add($smtp)
    $smtpbox = New-Object System.Windows.Forms.TextBox
    $smtpbox.Location = New-Object System.Drawing.Point(130,80)
    $smtpbox.Size = New-Object System.Drawing.Size(300,20)
    $formail.Add_Shown({$smtpbox.Select()})
    $formail.Controls.Add($smtpbox)
    $port = New-Object System.Windows.Forms.Label
    $port.Location = New-Object System.Drawing.Size(10,110) 
    $port.Size = New-Object System.Drawing.Size(120,20) 
    $port.Text = "Port:"
    $formail.Controls.Add($port)
    $portbox = New-Object System.Windows.Forms.TextBox
    $portbox.Location = New-Object System.Drawing.Point(130,110)
    $portbox.Size = New-Object System.Drawing.Size(300,20)
    $portbox.Text = '587'
    $formail.Add_Shown({$portbox.Select()})
    $formail.Controls.Add($portbox)
    $OKButton = New-Object System.Windows.Forms.Button
    $OKButton.Location = "150,160"
    $OKButton.Size = '100,30'
    $OKButton.Text = "Ok"
    $OKButton.DialogResult = [System.Windows.Forms.DialogResult]::OK
    $formail.AcceptButton = $OKButton
    $formail.Controls.Add($OKButton)
    $result = $formail.ShowDialog()

    # setting credentials
    $usr = $addressbox.Text
    $pwd = ConvertTo-SecureString $passwdbox.Text -AsPlainText -Force
    $credential = New-Object System.Management.Automation.PSCredential($usr, $pwd)

    # define email content
    $subject = 'TestMail.ps1'
    $body = "Questa mail è stata mandata da uno script PowerShell"

    # sending email
    $ErrorActionPreference= 'Stop'
    Try {
        Send-MailMessage    -From $addressbox.Text `
                            -To $addressbox.Text `
                            -Subject $subject `
                            -Body $body `
                            -SmtpServer $smtpbox.Text `
                            -UseSsl `
                            -Port $portbox.Text `
                            -Credential $credential
        $ErrorActionPreference= 'Inquire'
    }
    Catch {
        Write-Output "`nError: $($error[0].ToString())"
        $answ = [System.Windows.MessageBox]::Show("Sending alert email failed",'WARNING','Ok','Warning')
    }   
}

In the cmdlet Send-MailMessage I haven't found any parameter to force authentication. How can I effectively send an email?

Answer 1

The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.5.1 Authentication Required:

Solutions in order of likely hood to help.

1. Check if the user has 2fa enabled if so you will need an apps password
2. Check your Captcha loc
3. Look into Xoauth2

Answer 2

I solved the issue. As stated here , I have to:

1 - Force the script to use TLS 1.2

2 - Turn off two-factor authentication and allow access to insecure apps

Thank you DaImTo for the inspiration