Windows Server Essentials Experience Error Reports Emails

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I’ve been getting emails from Microsoft warning me that pretty soon, Outlook.com will require “Modern Authentication Methods.”

Modern Authentication Methods now needed to continue syncing Outlook Email in non-Microsoft email apps

I could not figure out why I was getting that warning because I use the current version of Outlook on my desktops.  But now I know why….

Up until a few days ago, I used  the Microsoft Outlook.com server to send me WSE Health reports everyday.  Prior to that, I used my own email account with my ISP but they started rejecting emails from my “Home” server emails many years ago.  Now Microsoft is doing the same.  Apparently I need OAuth2 authentication option which does not seem to exist in WSE.  I am wondering what people are doing.  I am running your WSE under Windows Server 2019.  Thanks for any ideas.

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Okay, I’m just about to release OAuth2 support for Microsoft 365 / Outlook.com accounts when emailing Health Reports from Windows Server Essentials. See: How to set up the Health Report Outlook Mailer

BTW, this was insanely hard to accomplish. I had to completely rewrite and extend the existing Health Report add-in and jump through a whole bunch of hoops to make this work. I should probably be charging something extra for this functionality, but I’ve decided to just include it as part of the WSEE Installer.

  • Mike
    Okay, I’ve just updated the documentation to include entering in the nativeclient Redirect URI. Hopefully that resolves the issue, but if not, then please do let me know.
  • CharliePonch
    Thankyou Mike. All working here! I had missed a step. Thankyou again. Charlie Ponchard
  • Mike
    That’s terrific news! Thank you for letting me know that adding the URI fixed the issue for you. Sorry for the oversite on my part. Take care and enjoy being able to send health reports from your Microsoft account. ; -)
  • CharliePonch
    Mike, just received this email from Microsoft do I need to be worried? — Upgrade now to keep building in Azure You’re receiving this email because your free credit has expired. Because of this, your Azure subscription and services have been disabled. To restore your services, upgrade to pay-as-you-go pricing. Keep using your configured services and data and get access to 12 months of popular services for free and more than 40 services that are always free.* Upgrade now > Beyond the free amounts, only pay for what you use each month. It’s easy to cancel, anytime. Your subscription data will be permanently deleted on 07 June 2025. Sign in and save any important data before then. Upgrade before 07 June 2025 to resume using your services with minimal interruption. If you need more help, submit a support ticket. *Based on resource and region availability. Account information Subscription ID: [Snip] Subscription name: Azure subscription 1
  • Mike
    Yes, as mentioned in my tutorial, you need to move your “free” Azure account to (Basic) “Pay as you go” pricing (within 30 days) to continue being able to access the Azure services. Since the “App registrations” service we’re using here is a completely free service in Azure, you will not be charged anything so long as you haven’t enabled any of the other “paid” services in your Azure account. I’m not sure why Microsoft doesn’t do this automatically for you, but I suppose they have their reasons. If I recall correctly, you can sign in to the Azure portal, go to “Subscriptions” and move to the “Pay as you go” pricing model from there: https://portal.azure.com
0

Well, that’s unfortunate, but I guess it doesn’t surprise me too much (i.e. I can’t really blame Microsoft for wanting to make connections to their email accounts more secure).

Since the Windows Server Essentials Experience (WSEE) is getting pretty long in the tooth now (Microsoft ends support for it on January 12, 2027), I highly doubt that they will ever update the Health Report Add-In to support modern authentication methods (such as OAuth2; which use token based authentication over the older and less secure password based authentication methods).

Thus, you’ll most likely need to source an email provider that still allows basic authentication methods when using their SMTP service in order to continue being able to email health reports to yourself. I’m quite sure that there are plenty of email providers like that still out there, but I myself don’t have any suggestions to offer you at this time I’m afraid. Hopefully someone else will jump in with one that works. And please do let us know if you happen to come across one that ends up working well for you.

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