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huzer1's avatar
huzer1
Icon for Nimbostratus rankNimbostratus
Jan 13, 2022

SMTP Proxy to Office 365

I'm trying to setup a proxy for SMTP going to smtp.office365.com. I've searched for SMTP documentation, the only one I've come across is quite dated with a version cap of 13.0. But using this as a re...
Niels_van_Sluis's avatar
Niels_van_Sluis
Icon for MVP rankMVP
Jan 15, 2022

The issue is with the certificate. Remove the client certificate from the virtual server. And make sure Send-MailMessage ignores the certificate.

$credential = Get-Credential
 
[System.Net.ServicePointManager]::ServerCertificateValidationCallback = { return $true }
 
Send-MailMessage  -to *****@hotmail.com -from *****@hotmail.com -subject "test" -body "this is a test" -smtpserver "192.168.178.200" -port 587 -usessl -Credential $credential