Participant

Answered

Mail.app wants to sign using key "privatekey" in your keychain

Forum|Forum|5 years ago
April 14, 2020
13 replies
110427 views

I wanted to sign a document using the sign/signature tool but for whatever reason, I ended creating a digital signature by mistake now I can't send the email without attaching a private key. I needed to remove this ASAP.

Adobe Reader doesn't allow me to remove the certificate. i.e clicking on the "Remove Id" does nothing.

SOLUTION:

1. Open Keychain on your mac "search 'keychain' in Spotlight (The magnifying glass icon on the top right of your screen) or Go to >Applications>Utilities>Keychain.app

2. Find the culprit certificate in the list

3. Take a back of the key in case something goes wrong by exporting the certificate.

4. >>> Delete

5. Restart the Mail app and also the Adobe Reader app.

Sorted 🙂

Security digital signatures and esignatures

Correct answer Jelle5C10

Hi,

When you open a new email, you can simply deactivate this digital encrypted signing by clicking on the little blue encircled checkmark in the new mail editor window. If you do this, it will stay unchecked for all subsequent emails. So no need to manually delete digital certificates from the keychain.

(I'm on Big Sur 11.1).

F

fred_2198

Participant

No need to delete certificates. There is an innocuous looking button on the message window, round, farthest to the right of the subject line. You undoubtedly clicked it by mistake, thereby asking Mail to encrypt your message, in which case it will be blue (on). Click on it again and it turns black (off). Problem solved.

P

peter_1978

Participant

I had this problem for 30 minutes, your advice solved my problem! Thank you for posting.

N

nancye35836001

Participant

I did what Huma5DDI suggested and delete the 3 certificates that were there. Two of them were dated the same as the date the problem started. Yippee, it worked! Here is where I found certificates in the Keychain Access area.

S_S

Community Manager

Hi @nancye35836001,

Thanks for letting us know it worked.

-Souvik

C

chris_3097

Participant

What culprit am I looking for?

S_S

Community Manager

Hi @chris_3097,

Hope you are doing well. Thanks for writing in!

From the above thread, it looks like one of the keys stored in your Mac's keychain is corrupted, causing a repetitive prompt.

The below steps could be performed to see if this is fixed.

1. Restart your Mac: A simple restart can help resolve temporary glitches or conflicts. Close all applications, including Mail, and then restart your Mac.

2. Reset Keychain: The issue could be related to a problem with your keychain. Resetting the keychain may help resolve the problem. Follow these steps:

a. Open "Keychain Access" from the Applications > Utilities folder.

b. From the menu, go to "Keychain Access" > "Preferences."

c. Click on the "Reset My Default Keychain" button.

d. Enter your user account password when prompted.

e. Quit Keychain Access and relaunch Mail to see if the issue is resolved.

3. Remove the problematic key: If the issue persists, you can try removing the key causing the problem. Follow these steps:

a. Open "Keychain Access" from the Applications > Utilities folder.

b. In the "Category" section on the left sidebar, select "Keys."

c. Look for the key named "privateKey" or any related key that may be causing the issue.

d. Right-click on the key and select "Delete" (or press the "Delete" key on your keyboard).

e. Enter your user account password when prompted to confirm the deletion.

f. Quit Keychain Access and relaunch Mail to see if the issue is resolved.

4. Remove and re-add email account: If the above steps don't work, you can try removing and re-adding the email account in Mac Mail. This will refresh the settings and might help resolve any configuration-related issues causing the error.

a. Open Mac Mail.

b. From the menu, go to "Mail" > "Preferences."

c. Select the email account causing the problem from the left sidebar.

d. Click on the "-" (minus) button at the bottom to remove the account.

e. Confirm the removal.

f. Then, click on the "+" (plus) button at the bottom to add the account again.

g. Follow the prompts to reconfigure the email account.

h. Check if the issue is resolved after re-adding the account.

Let me know if this helps.

-Souvik

A

Admired_partner4487

Participant

Many thanks for that. It worked.

I have been messing about with keychains all morning, nearly drove me mad.

You really saved my day.

Best wishes,

Michael Johnson

P

Pg36484352npn0

Participant

THANKS!

D

Don31611319s1gd

Participating Frequently

I found the 8-point blue shield on an outgoing email and unchecked it. That did it. Then deleted an extra signature in Keychain as described above. The blue shield either doesn't always show or it's so small that I never noticed it before. Nothing in the Mail Help files seem to describe it. That should be fixed.

J

julesbunny

Participant

I just had same problem caused by an Adobe Doc. At first I coulnd't see any certificates under 'my certificates' tab but they seemed to appear later. So I deleted both and got my email back. Phew. Thank you. 🙏

J

John37894184wc5i

Participant

Hi, I have wasted like half my day trying to work this out. Could someone please help. I tried signing an Adobe doc and created a key and now I cant use my email. I searched online, and got to the keychain access but I dont know which key or thing to delete? I have unclick the tick on mail so i can still send for now, but would like to know what to delete, I tried searching keychain and adobe, etc but unable to work out which one is the one affecting all this. thanks all for the help. (Freaking unreal this bs.. )

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Christine Valenti

Participant

"find the culprit certificate in the list"

uh, sure, that won't take long. i'm canceling my acrobat pro subscription after this. 30 minutes of my workday already i didn't want to spend effing around with this and problem not solved

G

gracoat

Participant

So the problem is actually not that tricky to understand. This might sound a bit like flames towards Adobe, but I assure you, it's not just them. There's so many moving parts in developing a propriety system of creating documents. It's a wonder any of it works! So, here it is:

Adobe creates a public key and a private key for your document. It then ecrypts it using those keys.

But who else has those keys??? Well, if you don't send the keys with the attachment, mail won't be able to encrypt it. Thus, the issue is with the keychain and mail not sending that public key with each new email. ONLY the email with the encrypted pdf has the keys attached.

It's implemented poorly. Adobe Acrobat should be completly in charge of encrypting and decrypting the message. NOT mail. It's a poor design that interferes with the way that Apple Mail works.

Making things worse, if you look on Apple's Support page, they point at Adobe. If you look on Adobe's site, they point at Apple. The truth is, Adobe made a system that works for the ONE DOCUMENT THAT YOU WANT TO SEND and no others. Apple's mail system has the ability to encrypt using keys, but not when it's intended for ONLY one recipient.

IMO, both parties are to blame. Apple already encrypts messages sent from mail and shouldn't allow 3rd parties to create and implement their own methods of encryption in Mail. Adobe is kinda shortsighted for using an encryption method that HARDCORE interferes with a Mail program that A LOT of people use. I'm sure it's a bug that's so far down the list of things to fix, that Adobe hasn't looked at it in YEARS. ...OR... and this is probably more likely, they hired someone not versed in the Apple Ecosystem to set up an encryption scheme in Acrobat, figured out how to implement it using the keychain, was able to prove that it works, and then the contract to code it was fulfilled. The coder was probably paid on fivr, and sucked at keeping documentation so no one at Adobe has any idea how to fix it.

That said, coders are people too. We all make mistakes. This one just affects those of us that use Apple Mail regularly.

The way to fix the problem is to create a new email FROM the address that's causing the problem.

On the far right side of the subject line, there's a lock looking icon that shows encrypted to not. (for the record, this shouldn't exist - Apple needs to remove this) Turn this button thingy into an X. Your message will not try to encrypt using Adobe's encryption keys now. It will, however, use the Apple Mail internal encryption which works just fine and is equally secure. If your messages STILL won't send, hit the deny button, quit Mail, open it up again, and ensure that encrypt button has the x in it.

PS - Adobe, if you're reading this, please remove Acrobats ability to encrypt the messages in the mail app. Package the PDF with the public keys, and send that in some super secret package with the recievers keys pre-installed in acrobat. There's no need to perform this trick in the Mail app. I'll send the report in the apple support forums as well. Apple should prevent third parties from doing this!

>>if you want to find the quickest and easiest way to perform a task for your company, find the laziest person you can to figout out how to complete said task<<