So you need a simple SMTP relay test? You can do it with P0werShell!

GregoryHall

So you need a simple SMTP relay test for Office 365
Introduction

I have been doing a ton of Exchange migrations lately and setting up internal IIS relays to smarthost to Office 365. In this I have found many issues with firewalls and various settings IT managers like to do to keep email traffic limited. In this I have had to figure out ways to test SMTP from telnet to PowerShell and this one is my favorite so I thought I would share.

Steps (4 total)
1
Open PowerShell
Right Click on PowerShell and Run As Administrator

2
Store your Office 365 Mailbox Credentials
get-credential will prompt you for the Office 365 relay mailbox creds. you need to store this in a variable so you can call it as one bit in the next command line.

$relaycreds = get-credential

3
Use Send-MailMessage PowerShell Command
now we can use the creds above to send a test email message using the Send-MailMessage command. [email protected] to the same user #you just stored the relaycreds in step one. [email protected] to another email address you have under your control so you can see it relay.

Send-MailMessage –From [email protected] –To [email protected] –Subject “Test Email” –Body “Test SMTP Relay Service” -SmtpServer smtp.office365.com -Credential $relaycreds -UseSsl -Port 587

4
Test the SMTP Relay
use the same command with a few changes to test the SMTP relay now.Do this from the server with IIS6 SMTP relay on or change localhost to the FQDN of your choice.

Send-MailMessage –From [email protected] –To [email protected] –Subject “Test Email” –Body “Test SMTP Relay Service” -SmtpServer localhost -Port 25

Conclusion

So really simple way to send emails now and you can see also from this command the ability to email from a scheduled task attached to event triggers. This will help you monitor your windows servers for those specific events that you care about.

Good luck

scottalanmiller

Awesome, that is pretty cool. Thanks.

Minion Queen

Thanks!

IRJ

Thanks! I was just talking about this with a friend the other day.

Dominica

Cool. This would have been handy for me to have a couple of years ago.

Dashrender

Nice one.

StrongBad

Good one, thanks.

Ambarishrh

Thanks!

Martin9700

Port parameter wasn't introduced until PowerShell 3.0, so you'll need to make sure you're on at a minimum of that before this will work. PowerShell 4.0 is the current version and 5.0 is coming out SOON. So if you're still on 2.0, upgrade now!