iMac says Connection Insecure. Failed to verify the server certificate

Question

Level 3

572 points

iMac says Connection Insecure. Failed to verify the server certificate

There's another thread about this, but it is expired. Yesterday I changed my Gmail password, and suddenly my old iMac's Gmail (High Sierra) would no longer connect. I got this dreaded "connection insecure - failed to verify the server certificate". All the solutions I found online were either about removing expired certifcates or turning off virus protection. Neither of those were my problem, the solutions did nothing.

I think Gmail has changed their technology so that it is no longer possible to add or edit an account through the regular "Google" mail UI, when you are on an older OS. I almost gave up, then I ran across a forum post on MacRumors called "How to Set up Gmail on Apple Mail?" (I would post a link but maybe that is not allowed?)

Anyway the solution is to use Google's "App Passwords". You create an App Password in the security section of your Google account. Then in the Apple Mail program, you create a regular old "Other" style email Imap account (NOT "Google"). Put your google email address and user name in there, use the default in and out servers, and instead of your password, you put in the App Password (without the spaces, it's just 16 characters). Voila, it finally worked...

iMac 27″, macOS 10.13

Posted on Jun 16, 2023 06:43 AM

Reply

Answer 1

Top-ranking reply

tonybathich

Level 1

10 points

Jun 19, 2023 11:57 PM in response to Bob Sabiston

Users on Macrumors' forum suggest adding your Gmail account manually instead of choosing "Google" under "Internet Accounts".

Anyways, to fix this, you simply need to download the latest Google's Root Certificates.

Here are the steps:

Simply go to this website: https://pki.goog/repository/ (this is a google website, no worries)
Expand Root CAa
Download the 4 certificates: under 'Actions' > Certificate (Der)
Use Spotlight to open "Keychain Access"
Goto File > Import Items... > and select the 4 certificates one by one
You may need to select "Always Trust/System" somewhere after the Import dialog opens...
Restart your Mac

I hope this helps,

Tony

(Thanks to Yousef AAN @ itsoftex.com, for his kind onsite IT help)

Reply

Answer 2

Bob Sabiston Author

Level 3

572 points

Jun 17, 2023 10:26 AM in response to BDAqua

The link is here: https://forums.macrumors.com/threads/how-to-set-up-gmail-on-apple-mail.2380991/

There are not complete instructions, but hopefully people with this problem can work out what needs to be done.

One thing to note is that you need to enter that App Password for both the incoming AND the outgoing SMTP server! That just bit me, when I tried to send from my account for the first time since changing it. I had not put the App password in the SMTP outgoing server, and so it wouldn't send it. Google won't show them to you after they are made, so make a copy! I ended up having to make a new App Password because I had not made a record of it the first time...

Reply

Answer 3

Jan 22, 2024 10:48 PM in response to Bob Sabiston

The "app password / add other type" solution worked for me. Then of course, my Mac downloaded thousands of old emails that I had already read. But still, a huge relief to be able to read my GMAIL on my iMac. Thanks!

Reply