S/MIME Certificate Verification Issue with Apple Mail for Gmail Account on MacBook Pro

I'm facing a problem with my Gmail account (let's say: myemail@gmail.com) when sending emails through Apple Mail on my MacBook Pro. The recipients are getting warnings that the authenticity of my S/MIME certificate cannot be verified, even though I am the authentic sender of these emails.


The warning message details are: "Mail was unable to verify the authenticity of the S/MIME certificate provided by 'myemail@gmail.com'. Messages signed by this user may be coming from a different source."

When I inspected the certificate in my MacBook Pro's Keychain Access, it showed that the certificate hasn't been verified by a third party. As I understand, this implies it's a self-signed certificate, which isn't inherently trusted by my system.



Here are the steps I've taken so far:

  1. Inspected the certificate in Keychain Access. It's not expired, but it's not third-party verified.
  2. Considered manually trusting the certificate, but I'm wary due to potential security implications.
  3. Thought about replacing the certificate with one from a trusted Certificate Authority, but I'm not clear on how to achieve this specifically with Gmail and Apple Mail.

I have not made any changes yet because I want to approach this situation correctly. I would greatly appreciate any guidance on how to resolve this issue, whether it's obtaining a new, trusted certificate, or if there's another solution I should consider.


Affected device: MacBook Pro

Software: macOS (latest version), Apple Mail (latest version)


Thank you in advance for your assistance!

MacBook Pro 13″, macOS 13.5

Posted on Jul 27, 2023 12:11 PM

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Posted on Apr 9, 2024 11:42 AM

You may have found a solution, but what worked for me was a solution from user @sparkhill in macrumors.


If you uncheck the digital signature icon when composing an email in Mac mail, it should stop asking for whatever certificate you have. (In my case a certficiate was added when I signed a pdf.)


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S/MIME Certificate Verification Issue with Apple Mail for Gmail Account on MacBook Pro

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