Connection Insecure: Unable to access / add email accounts

Several Mac users have reported an issue in which email accounts (Yahoo or Gmail etc) cannot be added. Users receive the following error message:

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

connection insecure

You may also see experience this problem when you want to send or receive mails, because Mail app on your Mac may not connect to your email account.

Even though this error message says this could be because of network or proxy setting issues, users have stated that they are experiencing this problem when in fact there’s no network connection or proxy issues.

Fix Connection Insecure Problem

If you are having this issue, here is how you can troubleshoot:

1-Try temporarily disabling your antivirus software. It is known that sometimes antivirus software may cause this problem. If this solutions does not solve your issue, read on.

2-Expired / revoked SSL certificates may cause this problem. Find and remove them. Here is how you can fix it:

a-Launch Keychain Access (Applications > Utilities).

b-Select “My Certificates”.

Keychain access

c-Now, find expired / revoked certificates, if any. Expired / revoked certificates will have a red X sign. Find also certificates with a red X mark saying “This certificate was signed by an untrusted issuer” or “This certificate was signed by an unknown authority”. When you find them, delete them.

expired SSL

d-When you are done, restart the Mail app.

Dr. Serhat Kurt worked as a Senior Technology Director. He holds a doctoral degree (or doctorate) from the University of Illinois at Urbana / Champaign and a master’s degree from Purdue University. Here is his LinkedIn profile.

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49 thoughts on “Connection Insecure: Unable to access / add email accounts”

  1. I recently tried to add an additional Google account to my Mac using the System Preference pane. However, I encountered the error Connection Insecure – Failed to verify the server certificate. This could be because of your network configuration or your proxy settings.

    This was on a newly configured MacBook Pro with macOS Mojave 10.14.1 that I had logged in with my Apple ID, which had been used previously so obviously was bringing along with it certificates from my previous systems via the iCloud Keychain.

    For me the fix was in the macOS keychain. Close System Preferences. Open Keychain Access (using macOS Spotlight search) and in the upper left, select “login” keychain, in the lower left, select “Certificates” and I had 2 (two) certificates listed “COMODO Client Authentication and Secure Email CA” and “UTN-USERFirst-Client Authentication and Email” I copied these out to my desktop (as a precaution) and then deleted these two certificates from the Keychain. I closed Keychain Access app and re-opened System Preferences. I can now add Google and Yahoo email accounts again from “Internet Accounts” preference pane.

    Reply
  2. hey there everyone. I really hope someone can help because I’ve been going crazy over this same issue. I just got my MacBook Pro and I’ve gone through the initial setup and now trying to log into my Google accounts, through Internet Accounts, but I’m getting the same message. I have nothing on this computer. No Ad blockers, no anti virus, nothing. Can someone help??

    Reply
  3. MacBook Pro out of the box and have installed NOTHING. Won’t allow a gmail account to be added to Mail. I guess I will install the Apple updates I just got notified about. I’m not feeling good about it.

    Reply
  4. none of this worked for me,I don’t have virus software, I have never had this trouble adding a gmail, just added a different one two weeks ago, I was deleting this account to figure something else out, but now I can’t get it back on. I donate have adguard, or avast or Qustudio, I have no certificates, and I’ve looked for adblockers. Its a Mac 10.13.5 (yes I need to update my software probably.. but seriously WTF?

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  5. Fixed it for all the mac users with no anti virus. the clock was set to the wrong time. I had to open the preferences and deselect set time automatically and then reselect. Then all is good!

    Reply
  6. Ok, for those who the above suggestions didn’t work, the next question is do you have Qustodio installed on your Mac? If so, it will need to be temporarily disabled to allow the account to be added.

    Note that Qustodio also stuffs up 1Password v6 in regards to working with browser extensions. While Qustodio has a help section describing things that stop it from working, it would be nice if they add information on things Qustodio stuffs up!

    Reply
    • Thank you, thank you, thank you!!! I was getting very frustrated and concerned I would have to call someone to fix this issue. Glad I kept reading the chain. Your callout on Qustodio was the issue, really appreciate your help.

      Reply
  7. Thank you!!!!!! I’ve had Genius phone calls and read every kind of voo-doo resolution on the internet–none were useful. I followed this group’s advice and resolved the problem in about five minutes!!!!

    Reply

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