I use Outlook to receive encrypted emails that are protected by a certificate stored on my smartcard. When opening these emails, a Windows Security prompt appears, asking me to enter the PIN for my smartcard to decrypt the message. Once the PIN is entered, I can access the email contents.

I’m looking for a way to automatically trigger the PIN entry dialog via code so that the user is prompted to enter the PIN without manually clicking on the encrypted email. The user will still need to insert their smartcard and manually enter the PIN, but I want the dialog itself to be initiated programmatically.

I would prefer to implement this solution in PowerShell, an Outlook macro (VBA), or Delphi. However, I encountered an issue: when attempting to display the email using MailItem.Display(True), the PIN dialog does not appear. Instead, the following error message is shown: “The name of your digital ID could not be found by the underlying security system.”

Has anyone experienced this or have suggestions on how to automate the process while keeping the PIN entry manual and secure?

Thank you in advance for your help!

​I use Outlook to receive encrypted emails that are protected by a certificate stored on my smartcard. When opening these emails, a Windows Security prompt appears, asking me to enter the PIN for my smartcard to decrypt the message. Once the PIN is entered, I can access the email contents. I’m looking for a way to automatically trigger the PIN entry dialog via code so that the user is prompted to enter the PIN without manually clicking on the encrypted email. The user will still need to insert their smartcard and manually enter the PIN, but I want the dialog itself to be initiated programmatically. I would prefer to implement this solution in PowerShell, an Outlook macro (VBA), or Delphi. However, I encountered an issue: when attempting to display the email using MailItem.Display(True), the PIN dialog does not appear. Instead, the following error message is shown: “The name of your digital ID could not be found by the underlying security system.” Has anyone experienced this or have suggestions on how to automate the process while keeping the PIN entry manual and secure? Thank you in advance for your help!   Read More

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