Outlook for Mac login prompt when signing e-mail with personal certificate

Jakub Škácha 0 Reputation points
2023-09-03T11:39:01.8633333+00:00

Dear all

Please could you help me get rid of the annoying login prompt whenever I am sending an e-mail with my Outlook for Mac ?

The reason is most probably, I am using digitally signed e-mails, using my personal certificate. When sending the e-mail, Outlook needs to connect to Keychain, where the certificate is stored.

However, I am not able to find the way to tell my Mac, that Outlook can do this even without me authorising him every time.

Thank you, every help will be appreciated.

Outlook
Outlook
A family of Microsoft email and calendar products.
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Office Mac
Office Mac
Office: A suite of Microsoft productivity software that supports common business tasks, including word processing, email, presentations, and data management and analysis.Mac: A family of Apple personal computers that run the macOS operating system.
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  1. Faery Fu-MSFT 16,921 Reputation points Microsoft Vendor
    2023-09-04T05:11:08.8633333+00:00

    Hi @Jakub Škácha ,

    According to my research, this issue may be caused by duplicate tokens in the keychain or by moving Office to a different location than the default /Applications folder.

    To resolve this issue, you can try the following steps:

    • Update your Outlook for Mac to the latest version, some issues will be fixed in updates. Choose Help > Check for Updates
    • Delete any cached passwords and modern authentication tokens from the keychain.
    • Lock and unlock your login keychain.
    • Grant access to the keychain when prompted and sign in to your account associated with Office.

    Here is an additional document for your reference: Office for Mac repeatedly requesting keychain access

    I hope this helps you fix the problem.

    If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

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  2. Jakub Škácha 0 Reputation points
    2023-10-27T08:33:34.6766667+00:00

    Sorry for the delay I was quite busy.

    No, sadly, it did not help.

    User's image

    This is how the login screen looks like. And it only appears, when I hit the send on my e-mail.

    I want the emails to be digitally signed by certificate, which I have installed in the keychain under system section.

    Thank you for your help.

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