Can't add gmail account - Connection Insecure

Apple mail on Beta - 4


Using a Gmail account that is synced using iCloud syncing. On just one Mac I keep getting asked to add the password, and when I say yes, the Internet accounts pat of System Preferences comes and and then shows me a message



"Connection Insecure


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


But it works fine on other machines, and on my iOS devices.

Replies

Have you tried completely removing that account from Internet Accounts in the System Preferences, and then adding it again?

I did that a couple of times.


It removes the account from all my other desktops - as it's synced with iCloud Keychain.


When I try to add a new Gmail account from this one machine I get the "Connection Insecure..." message.


So I add it to Internet Accounts on another machine, and it works. So when the accounts sync back the machine with the problem I get an alert asking me to enter the password, which then gives me the "Connection Insecure..." message. So it's just on this one machine. The account settings are the same, set up from the sync, so I don't have to do anything. Don't know what configurations or proxy settings (which I don't have set) I need to look at.

It may be related to an ssl certification issue that has been the cause of quite a few symptoms throughout these betas. You can check it out as follows:


  • Open Keychain (by pressing CMD+Space and then typing “Keychain”).
  • Then type veri into the Keychain app's searchbar.
  • For each of the VeriSign certificates, do the following:
    • Check that the certificate is still valid (far right column) and delete it if it isn't.
    • Double-click it, which brings up it's own window and expand the "Trust" menu.
    • Make sure "When using this certificate:" is set to "Use System Defaults", not "Always Trust".
      • The remaining 10 should be left at "no value specified".
  • I did that and there were no expired certificates, or trust settings that were not set to use system defaults.


    However, I did notice that everytime I opened mail I was being warned that the GPGMailBundle was not compatible and was being disabled. I deleted the plugin and restarted Mail - And now I can enter my password. 🙂


    Not sure if it was looking at the certs, or deleting the bundle, but something made that one account come back to life.


    Thanks for helping, Max.

    Also running into this issue. Tried those steps with no results. I've had this since 10.10 DP1, but I believe the error message was added in DP3 or DP4.

    Just started running into this today. It now happens every time I try to add any Google account via directly in the Mail app or through the Internet Accounts dialog.


    Any other thoughts on how to resolve this?

    Are you using Google's 2 step verifications? Do you have Google's authenticator app for generating unlock codes off your iphone? You can also generate app specific passwords in Google's security settings and use that password instead of your normal password to let your Mac have full gmail access.

    • I also had this problem on my MAC. No problem getting the gmail on my Galaxy S9 phone via my android mail app but no joy on my MAC. I am on a 2013 MAC running High Sierrra (yes, it is an old-timer by today's standards). The app specific password option mentioned in Riptide360's response worked perfectly for me.Thanks Riptide360!!

    Add a Comment

    Same problem here after installing El Cap GM version.

    Anyone found a solution?

    I resolved it by deleting login certificates using Keychain Access app installed in OSX

    I had some problem with 10.11 GM. In my case the certificates were still valid but had a red "x This certificate was signed by an untrusted issuer". Deleting these certs (two in my case) fixed the problem.


    I suspect these certs are left over after updating and no longer trusted (Verisign moved to longer keys and/or more secure hashes: http://www.symantec.com/page.jsp?id=roots and Apple now requires at least 2048 and SHA-2 IIRC)

    thank you so much .. this did the trick ... I had the two verisign certs with the red mark in the Login/Certificates container in the keychain as well, once deleted them issue was gone


    Rgds

    Having the same problem as you. I have no login certificates with red x's or that are expired.

    Hi all, I just had this problem on a machine with an (almost) clean install of 10.11 on it. I say almost: the only thing I'd installed already was Avast. Turns out their web filtering function was trying to MITM the secure connection to Google and it was failing. Turning off web filtering let me add the Google account successfully.

    Thank you SO much I had no idea what to do but this worked perfectly!

    Thanks ! It worked..! 🙂