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Engaged Sweeper II
Unable to make connection to Office 365 via the "Email Alerts" configuration page.

I have everything configured as below:

SMTP server -> smtp.office365.com (port 587)
Security -> Explicit TLS/SSL
Server Requires Authentication -> Checked and have valid creds in there for authenticating.

When I test the reply is the target actively refused the connection. There is no issue with my firewall as I have another application that allows this same setup to work.

Engaged Sweeper II
That's a great idea!! I'm going to try to do that extra step and see if that helps my email drama. I will let you know if this has me doing to happy dance or i'm still lol
Champion Sweeper III
you could add SMTP to the server where lansweeper is running (assuming that feature is an option in the OS you are using)
set it as a local SMTP relay accepting for your domain.
then configure that relay to send like Veem does?

in IIS you could need the 6.0 compatibility if I recall to see and configure the SMTP queue.
I had to set one of my boxes up as an internal relay for several other apps and devices, then I made it so only that one relay needed configuration and every other system uses mailrelay.mydomain.local in their config and even anon works.

Just a thought.
Engaged Sweeper II
AZHockeyNut - Thank you, I sure did read that and neither Option 1 or 2 works for me with this application, but I have other apps such as Veeam that sends alerts via email (Option 1) so its frustrating me why Lansweeper won't work. Not sure where the difference is in how it handles SMTP requests.

I've just taken LanSweeper out of the equation and used Powershell from the server running LS to connect to exchange online and it gets denied also so its not Lansweeper issue for me. But I could use the mail tester in LS with Exchange Web Services and it connects fine, just not SMTP. UGHHHH!
Champion Sweeper III
I am sure you have check it and tested it but... https://support.office.com/en-us/article/How-to-set-up-a-multifunction-device-or-application-to-send-email-using-Office-365-69f58e99-c550-4274-ad18-c805d654b4c4

offers different options for allowing devices and applications to relay thru office 365.