SimpleHelp Community

Use O365 email for Tech MFA and other emails


Does anyone have an indicator on the settings of having SH server send emails via an Microsoft 365 account? I have a dedicated account setup and licensed for messaging/email from SH.
Following O365 documentation, the server is on port 587 with STARTTLS.
I seem to be getting a various handshake errors, depending on whether I try TLS or SSL


Modern Authentication - google it.
If you really need this to work then enable Authenticated SMTP for that mailbox.
Also use legacy SMTP
Google this: Exchange Online endpoint for legacy TLS clients using SMTP AUTH


Thank you! That did the trick.


I’m trying to sort this out - did you use legacy SMTP or configure Modern Authentication?


Does anyone have instructions for setting up (or find existing) Client ID and Client Secret for Office 365 oAuth2?


I got through the Azure AD setup and got a message "Email Configuration Complete - You have successfully setup OAuth email authentication.

But when I send a test I get this:


finally got this working. followed the guide

In Simplehelp,
I had to use
-Use ssl/tls if available (require didn’t work for me).
-port 587
-Select “Azure AD”. Using office365 didn’t work for me.


I’ve had this project on hold while busy with some other things - will let you how it works out for me using your guide.


Hi Mike,

I’m not sure what value to use for Client ID - I tried the value provided when you create the secret, then I tried my org’s ID but both gave me this error:

AADSTS700016: Application with identifier ‘xxxxxx-xxxx-xxxx-xxxx-xxxxxxxxxxxx’ was not found in the directory ‘DCS Group’


Found the application ID - now I’m getting this:

Sorry, but we’re having trouble signing you in.

AADSTS9002325: Proof Key for Code Exchange is required for cross-origin authorization code redemption.

EDIT - figured it out - I switched from “Single Page Application” to “Web”

EDIT 2 - Still getting this on test



The client ID is the Application (client) ID from the Overview screen.

The Client Secret is the Secret Value when you create the Client Secret. (You only see it when you create the client secret. If you didn’t copy it down, delete it and create a new one).


I gave up on this and took @Nathan_Kull 's advice and signed up for an inexpensive SMTP service. I chose AuthSMTP as I’ve used it in the past and was happy with the low annual price ($36) and deliverability.

BTW, I had the correct Cliend ID and secret.