sendMail.exe alternative [closed]

Have a bunch of in-house batch scripts and what-not that utilize sendEmail.exe, which is an old perl auto-emailer application which can be found here:

github for sendEmail.exe

The problem is that with our migration to office365, and our security policies, smtp requires startls. SendEmail does not support startls (or have a startls option)... while there are options for both ssl and tls: yes/auto/no, none of them work.

One option would be to create something new with python and the smtplib library to replace sendEmail.exe, but I'd rather not re-create the wheel here.

Are there any other popular free utilities or programs out there, that I could easily swap out to fill this role?

I've got another solution for you, and it's your old trusted SendMail.exe to be used in conjunction with Stunnel. Stunnel does support STARTTLS, and it runs under Linux/Windows/MacOS/*NIX.

What's Stunnel now about, you might ask? Well, this:

Stunnel is a proxy designed to add TLS encryption functionality to existing clients and servers without any changes in the programs' code.

So basically it enables your old solution to speak TLS; Stunnel does the encryption part of it and SendMail.exe the rest.

This might be the easiest solution for you; instead of replacing SendMail.exe, you are just adding Stunnel which can be done quite fast.

I would replace this with a more native approach using PowerShell. As Send-MailMessage is now obsolete, that leaves us with System.Net.Mail: MailMessage & SmtpClient. Supposedly your scripts can pass the variables (and you can fill the missing) to:

$mailMessage = New-Object System.Net.Mail.MailMessage($fromAddress, $toAddress, $subject, $body)
$smtpClient = New-Object System.Net.Mail.SmtpClient($smtpServer, $smtpPort) 
$smtpClient.EnableSsl = $true
$smtpClient.Credentials = New-Object System.Net.NetworkCredential($smtpUsername, $smtpPassword)
$smtpClient.Send($mailMessage)