About a week ago, I was prompted to reset my Yahoo e-mail password. So I went to System Preferences -> Internet Accounts and double clicked on Ymail (the Yahoo e-mail account). I saw this screen:

Ymail empty

Followed shortly by this error message:

Connection Insecure. Failed to verify the server certificate. This could be because of your network configuration or your proxy settings.

Dismissing the error message does nothing to the first window, and eventually I have to cancel.

Strangely, I noticed this same behavior has happened when I double-click on my Gmail account, despite the fact that the password still seems to be valid.

I have seen this behavior both at my home and my local coffee shop. To my knowledge, I am not using a proxy. What can I do to solve this "Connection Insecure" problem when trying to manage a Gmail or Yahoo account?

  • The Message says nothing about your Password but about the Servers Certificate. The Problem may either be a Connection issue to the Servers Certificate itselfs so your Mac can not verify if the Servers Certificate is correct or not. Or he cant connect to there because something is blocking it eg. a Proxy. Are you behind a Firewall? Sometimes they act also like a Proxy. It may also be that there is a Trojan or Virus on your Mac that acts like a Proxy. – konqui Oct 20 '17 at 11:27

Check the Login/Certificates container in the keychain for anything with a red mark that says "Certificate is invalid". It's probably an old CA on the box that's conflicting with the current one from those accounts.

  • also didn't work for me. – Chet Nov 21 '18 at 5:58

Upgrading from macOS 10.11 to 10.12 mysteriously fixed this problem. I don't know what the problem was, but that fixed it.

  • didn't work for me – Chet Nov 21 '18 at 5:58
  • @Chet You can ask a new question, or add additional information about the problem to help diagnose why these instructions didn't work for you. – Thunderforge Nov 21 '18 at 15:13

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