August 20, 2025Aug 20 I have been using hotmail to send my alerts etc. I noticed now I am not getting anything. Getting this error message:Unable to send test message: 535: 5.7.139 Authentication unsuccessful, basic authentication is disabled. [SJ0PR03CA0077.namprd03.prod.outlook.com 2025-08-20T19:27:01.388Z 08DDDEF3173BAC45]Not sure what might have changed.
August 20, 2025Aug 20 Community Expert Due to 2fa and new Microsoft APIs you need to go into the email for Microsoft outlook and enable pop/imapSometimes you need to setup an app password login for the app to use password wise and connect and use the mail box.https://support.microsoft.com/en-us/account-billing/how-to-get-and-use-app-passwords-5896ed9b-4263-e681-128a-a6f2979a7944Hotmail was converted to live which converted to outlook for the backend email servers. I use a live account for unraid...https://mailtrap.io/blog/hotmail-smtp/To configure unRAID to send email notifications via a Hotmail (Outlook.com) account, you'll need to use the correct SMTP settings and potentially enable less secure authentication, according to an Unraid forum thread. The key settings are: SMTP Server: smtp.live.com or smtp.office365.com or smtp-mail.outlook.comSMTP Port: 587 (for STARTTLS encryption) or 465 (for SSL/TLS encryption)Username: Your full Hotmail/Outlook.com email addressPassword: Your Hotmail/Outlook.com account passwordEncryption: STARTTLS or SSL/TLS (if supported) Edited August 20, 2025Aug 20 by bmartino1
August 22, 2025Aug 22 Author I am getting this now:ServerHostname or IP of Email serverUnable to send test message: The operation has timed out.
August 23, 2025Aug 23 Community Expert 17 hours ago, rmilyard said:I am getting this now:ServerHostname or IP of Email serverUnable to send test message: The operation has timed out.that a generic time out/ It can't reach host. so double check your dns settings(known issues if using tailscale...) and make sure you cycle through and test theses smtp servers.SMTP Server: smtp.live.com or smtp.office365.com or smtp-mail.outlook.comdepending on the account depends on the backend stie.https://support.microsoft.com/en-us/office/pop-imap-and-smtp-settings-for-outlook-com-d088b986-291d-42b8-9564-9c414e2aa040most likely: SMTP server namesmtp-mail.outlook.comwhere you may need to ping smtp-mail.outlook.com to get an ip and use the IP address. As it seems like you have a network issue preventing internet access or preventing crosstalk to Microsoft server.not Enouth info to assist otherwise.
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