Mail security certificate issue after creating self-signed certificate

Question

Mail security certificate issue after creating self-signed certificate

Long story short, ever since I created a self-signed certificate a couple of weeks ago for encryption having to do with a specific app, my outgoing (not incoming) Mail on Mojave constantly shows as "Unable to verify message signature" even though it has no problem sending.

I found the certificate I created within Keychain Utility, I deleted it, and the problem went away.

But a few times a day or so I'll be composing an email, and I'll realize that the security "digital signature" indicator is on the right side of the new email I'm composing. And I'll look in Certificates in Keychain Utility and see that the same certificate with my name on it that I deleted has returned.

Then I delete it again and the problem goes away for a little while.

How can I make the certificate stop constantly regenerating?

I've attached a screenshot of what the indicator looks like when I'm composing an email. It's a little lock icon next to a checkbox of sorts. When I see this, I know the problem has returned and I have to delete the certificate or else my recipients will get my email but they see an "Untrusted Signature" warning when they receive my email.

Thanks for any help getting rid of this issue.

Posted on May 10, 2022 1:29 AM

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Answer 1

Top-ranking reply

BDAqua

Level 10

245,483 points

May 10, 2022 3:28 PM in response to DigitalDuderino

I think were dealing with a corrupt file, it'd be work to test that idea, but...

To find out if it's system wide or user specific, try this...

Open System Preferences>Users & Groups, unlock the lock, click on the little plus icon, make a new admin account, log out & into the new account.

Does it work in the new account?

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Answer 2

May 10, 2022 3:38 PM in response to BDAqua

That is always a good idea to test things in another user account, but unfortunately that would require me actually working for hours or all day in another user account since the issue can take hours to reappear, and I have so much software and custom settings, etc in my main account that that's not an option for me while I'm working.

But here's an update, last night when I saw the issue appear again, I found the certificate that keeps re-appearing in Keychain Utility. Then I double-clicked on it and revoked it's access to the Mail app from the settings that you can modify, saved changes, and then deleted the certificate. That was probably 13-14 hours ago. My computer has remained on the entire time since then and, so far, I have not seen the issue come back or the certificate suddenly show up again in Keychain Utility.

This is the longest period of time I've gone without seeing the problem, so my fingers are crossed, but I will keep expectations low and watch out for it.

Will post back here about any success or failure if it reappears.

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