Ken has a number of emails running in Outlook. A few are Gmail. Everything works fine at home, but Gmail thinks he's being hacked and won't let him log in when he uses a hotspot or VPNs. So he has to go outside the VPN to log into Gmail in order to register the IP. And that only works sometimes. Leo says to go into the Outlook settings and make sure you have a proper profile created using GMail's SMTP for those Gmail addresses, along with your login and password. Leo suspects that is where the hiccup lies. Also, turn on two-factor authentication. It'll also require an app-specific password rather than your Gmail password. You can google how to generate that. Then use the app password in Outlook to log into Gmail. Here's also a link to how to keep Gmail from blocking outlook.