Modern Auth Requirement: As of late 2024, Microsoft deprecated basic authentication for outlook.com, pushing accounts to use Microsoft 365 Exchange protocols, which often override user-set IMAP/SMTP configurations.

Use Surfshark's "Split Tunneling": This is the best long-term solution. You can tell Surfshark to ignore your Outlook application, allowing it to use your regular, unprotected internet connection, while your browser remains protected by the VPN.

Use Webmail with VPN: If you only need the VPN for browsing, use outlook.office.com in your browser while the VPN is on, and only use the Outlook App when the VPN is off. 

   VPN On: Use Port 465 + SSL, or use Split Tunneling for Outlook.
   VPN Off: Ensure port is set to 587 + STARTTLS (standard for Outlook

Hi, PathMan Solutions to Fix Sending Issues with Surfshark It sounds like you correctly identified the culprit. Your diagnosis of the issue— Surfshark blocking outgoing SMTP ports (587/465/25) to prevent spam—is a well-documented issue with this VPN provider. Here is a breakdown of why this happened and how to resolve it permanently. Why Your Settings "Magically" Changed Automatic Detection: When Surfshark is on, it routes traffic through a different server. Outlook often tries to "repair" or "reconfigure" settings based on this new network, causing the SMTP server to change to outlook.office365.com. Modern Auth Requirement: As of late 2024, Microsoft deprecated basic authentication for outlook.com, pushing accounts to use Microsoft 365 Exchange protocols, which often override user-set IMAP/SMTP configurations. Use Port 465 + SSL (Confirmed Solution): As you noted, Surfshark blocks port 587 (typically used with STARTTLS). They specifically allow Port 465 combined with SSL/TLS encryption. Settings: Outgoing Server: smtp-mail.outlook.com | Port: 465 | Encryption: SSL/TLS. Use Surfshark's "Split Tunneling": This is the best long-term solution. You can tell Surfshark to ignore your Outlook application, allowing it to use your regular, unprotected internet connection, while your browser remains protected by the VPN. Action: Open Surfshark - Settings - VPN Settings - Bypassing (Split Tunneling) - Add Outlook to the list. Switch Protocol in Surfshark: Sometimes simply changing the VPN protocol from WireGuard to OpenVPN (UDP or TCP) allows SMTP traffic to pass through. Use Webmail with VPN: If you only need the VPN for browsing, use outlook.office.com in your browser while the VPN is on, and only use the Outlook App when the VPN is off. Summary Checklist: VPN On: Use Port 465 + SSL, or use Split Tunneling for Outlook. VPN Off: Ensure port is set to 587 + STARTTLS (standard for Outlook