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

Question

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.

Answer 1

Sorry for the delay I was quite busy.

No, sadly, it did not help.

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.

Answer 2

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.

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