Apple Mail - Email Certificate: Untrusted Signature

THANK you so much for assisting me.

The information on that support page appears to be dated. I have the latest MacOS 14.1.1, and it appears slightly differently… provided I'm following correctly.

Screenshot from link:

So I assume I would just do the reverse to turn encryption off?

1. Open "Settings app" …? Presumably that means the "System Settings" app (best to always use the exact name, but ok)…

2. Chose "Mail > Accounts" there's nothing in Systems Settings called "Mail" and then "Accounts" but there are "Internet Accounts" where mail accounts are found (see image).

…continued below…

3. I'm in the email account. I see nothing anywhere that says "Advanced" settings. I click on "Details…" and it shows:

OR … Am I looking in the wrong place?

.

> The original posting looked like an iPhone screenshot, and no platform was mentioned.

I explained that other people were getting errors when they received my emails. I thought it was clear that this was an error that someone sent me as a screenshot.

> You or someone else with access to this Mac have previously installed a personal certificate,

> or potentially have a certificate present on a connected security key.

Ok.

> Do NOT delete any certificates located during the following

Ok.

> Do you have a security key (USB-A or USB-C device) installed in your Mac?

No.

> Do you have an identity preference selected…

Yes.

> …in Keychain?

I guess this is stored in Keychain.

I have two accounts. I think I see where this is headed.

Apologies for the long explanation below, but the next obvious question is going to be to ask why I have two Apple IDs, so I'm just going to get this all out of the way…

——————————————————————————————————

Decades ago I got an early iPod Gen 3 (2003).

I was set up with an Apple ID.

For a long time I carried three devices:

An iPod, a Motorola Razr, and a PalmPilot… but I digress.

Then my first iPhone was an iPhone 4 (2011).

When I went to my appointment at the Apple Store, they just set up a NEW Apple ID. The hard drive the iPhone 4 could not handle all the songs on my then current (later) iPod. So it was only many, many years latter, when iPhone hard drives were larger, that I went to move all my music from my iPod to my iPhone (2014 I think).

ONLY THEN did I realize that the two Apple IDs I'd been set up with could not run on the same phone, at the same time. So I would have to switch back and forth between two IDs, to use my Apps (bought on my iPhone Apple ID) and my Music (bought on my iPod Apple ID). This was a HUGE pain in the rear.

Over the years, I would periodically ask if Apple was ever going to allow merging two Apple IDs into one. The answer was always NO. Apple does not, and will never allow two Apple IDs to be combined into one.

Sooo… about a year ago, an Apple tech suggested I could solve the problem:

I could set up one Apple ID as the Main account on a "Family Plan," and set up the other Apple ID as a family member, and I could share all my songs. So some devices are default to one account, some to the other, but they're both sharing music and apps.

It looks like THIS is probably causing the problem?

Firstly— Thank you so much for taking the time to assist.

I was sitting here writing a reply to you from this post from last night, and decided to test it, and on my **desktop**, the error was gone!

I didn't know why, or what fixed it.

But now the emails were coming in as Signed,

with a checkmark security seal, and everything (see image)… [not so fast]

When I went to bed last night, they were still giving errors. 👀

I have no idea. Maybe something took time to propagate?

-----

Then, my enthusiasm dropped.

I checked the EXACT SAME EMAIL from my iPhone (sent to myself), from the same email address, and it has the Untrusted Signature warning!!!

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Same email account—same exact email, even—simply opened on another device.

WTF?

"Your certificate may be issued by an organization that…"

I don't even know what this means. I've been using email for over 30 years, and I've never had to set up a S/MIME certificate in my life.

I don't even know what anything you're saying even means.

I have no idea what any of this means. Until this incident, I'd never heard of a S/MIME certificate in my life, and I've been on email since the 90s.

I don't know what an "intermediate certificate" is.

I'm just trying to send emails.

Thank you.

Recipients of my emails have pointed out to me that they get an all-caps, red-type scare alert:

ALERT: ** UNTRUSTED SIGNATURE **

…at the header of every email they get from me.

Sometimes with additional copy like:

🛑 'The signature on this email is not authenticated, and the email may have been altered in transit.'

I fear some may be filtering into junk mailboxes (?), to never be seen at all. I'm pitching for new project work right now. Solving this is existential, and NOTHING IS WORKING.

In your prior reply, you suggested to simply turn off encryption.

Is not having my emails encrypted going to trigger a different scare alert?

ALERT: ** THIS IS AN UNENCRYPTED MESSAGE **

…or some such?

Because if I can just figure out how to turn encryption off, that may be the best immediate solution.

I see two certificates:

com.apple.systemdefault

com.apple.kerberos.kdc