Why does Mail ask for keychain password and will not send email without it

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Level 1

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Why does Mail ask for keychain password and will not send email without it

Problem probably triggered by electing to use digital signature on DocuSign for a pdf document. For whatever reason Apple "Mail" program was stuck in a loop asking for keychain password for user and having only options of "Allow", "Deny", and "Allow Always." User password (and Apple password) did nothing and Mail application was rendered useless.

Does anyone know why Mail asks for Keychain user password? The icon in upper right hand of email message showed seal (stamp) with a checkmark just to right of a locked lock icon. By selecting the seal icon it changes to an "x" I believe indicating the email is not encrypted, but still Mail was not working.

Finally called Apple Support and a very accented voice led me through a couple options, the last one being to change my Mac user password through System Preferences/Users & Groups and unlocking and then selecting "Change Password". This solved the immediate problem but I still do not understand it.

Mac mini, macOS 12.4

Posted on Jun 29, 2022 10:41 AM

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Answer 1

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leroydouglas

Community+ 2024

Level 10

188,778 points

Jun 29, 2022 11:25 AM in response to forrests

forrests wrote:

I think the answer is "Yes" but unknowingly. As I mentioned I was using an electronic document signing website, "DocuSign" and also Adobe Acrobat PDF viewer. I believe it was Adobe Acrobat that asked me if I wanted to create an electronic signature and I responded "Yes." I never elected or knew that I was likely creating a certificate for use with encryption--there was no clear notice or choice to do so--just to create an "electronic signature." Once Mail starting asking for keychain password, I was unable to discern or satisfy exactly what was demanded by macOS or Mail or a way out.

Good questions for your third party apps if in doubt search the developers website or contact their: Support/Help/FAQ/Known issues/compatibility/Updates.

You would hope encryption is being used if on-line...

or

Keep in house Preview.app if possible.... I will say Preview is not a "true PDF editor", it has its limits.

Fill out and sign a PDF form in Preview on Mac - Apple Support

for your Mac built in Keychain Access.app—leave the log-in unlocked

Keychain Access User Guide for Mac - Apple Support

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Answer 2

forrests Author

Level 1

23 points

Jun 29, 2022 11:01 AM in response to Seshtai

I think the answer is "Yes" but unknowingly. As I mentioned I was using an electronic document signing website, "DocuSign" and also Adobe Acrobat PDF viewer. I believe it was Adobe Acrobat that asked me if I wanted to create an electronic signature and I responded "Yes." I never elected or knew that I was likely creating a certificate for use with encryption--there was no clear notice or choice to do so--just to create an "electronic signature." Once Mail starting asking for keychain password, I was unable to discern or satisfy exactly what was demanded by macOS or Mail or a way out.

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Answer 3

Seshtai

Level 1

129 points

Jun 29, 2022 10:49 AM in response to forrests

I have seen this behaviour when using encryption with certificates. do you have something like this set up on Mail?

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Why does Mail ask for keychain password and will not send email without it

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