I was using a Windows command line blat.exe mailer with stunnel along with a gmail account to send emails from a Windows command line batch file. Gmail started requiring I se the gmail account to allow "less secure" sign in options. That worked for a while, but in May 2022, gmail discontinued that option. It sounds like you can set two factor on the gmail account and then generate an app password for the gmail account. So I did that. I'm stumped on how to get either blat or stunnel to use that gmail app password though. Any ideas? Blat is looking super old though. I see when I set up this computer to with blat-stunnel-gmail, that I ran a line with blat.exe to store the gmail password. I don't see a way to store an app password, but blat is old. This is blat. http://www.blat.net./ Looks like the last update was in 2012, so app passwords may not have even existed then. Is there any way to stunnel to store a gmail app password? My goal is just to send an email from a Windows machine with either a Windows batch file or PowerShell script. It's not mission critical. It's for home use. I just like to get email alerts when my home machines complete some task. If something else works, I'm interested. It needs to work in a batch file though, or at least powershell if a batch file can't work. For my previous set up, I just kept stunnel updated, initially set up blat with the email information, and used only a batch file with blat to send emails from a gmail account. And then it was making sure less secure apps was an option on the gmail account. Now it's been broken for almost a year.