Ubuntu: Testing authenticated SMTP over TLS/SSL

SMTP mail relays exposed to the internet typically use a combination of SSL and authenticated SMTP to avoid abuse by malicious actors.

This is an excellent choice from a security perspective, but makes smoke testing a bit more complex than just opening telnet.

Continue reading “Ubuntu: Testing authenticated SMTP over TLS/SSL”

Sending SMTP Mail from Windows Using PowerShell

When working from the Windows command line, you can do a quick test to validate your SMTP connectivity using PowerShell:


c:\> Powershell -executionpolicy bypass

PS c:\> Send-MailMessage –to <TO> –from <FROM> –subject "testing123" –body "this is a test" –smtpserver <SMTPServer> -port 25

And if the mail server is accessed over TLS/SSL with SMTP authentication enabled:

PS c:\> Send-MailMessage –to <TO> –from <FROM> –subject "testing456" –body "this is a secure test" –smtpserver <SMTPServer> -port 587 -UseSsl -Credential (Get-Credential)

This is easier than going down to telnet, which is typically not installed on a modern Windows host: Continue reading “Sending SMTP Mail from Windows Using PowerShell”