Asked to enter PIN multiple times when sending Digitally Signed emails

Hey everyone, I have been having a very difficult time trying to figure out why my co-workers and myself are being asked to enter our PIN multiple times when digitally signing emails. My co-workers are looking to me for a solution, however
I just cannot seem to find any information on as to why this is happening. Could anyone possibly shed some light on why this may be happening? Thanks in advanced!!!
P.S. We are using Outlook 2013

Hi,
Let's troubleshoot this issue by the following steps:
1. Start Outlook in Safe Mode to determine whether it's 3rd-party add-ins related:
Press Win + R, type "outlook.exe /safe" in the blank box, press Enter.
If no issue in Safe Mode, disable the suspicious add-ins to verify which on caused the problem.
2. Go to Control Panel and search for "Manage computer certificates" then open it, find the certificate and right click on it, choose Properties -> under General tab select "Enable all purposes for this certificate" -> Apply ->
OK.
3. If you create a new Outlook profile, does this issue persist? A new profile will provide a new environment for the account and it will not remove any information from the old profile. A profile corruption may be the source of this issue.
How to create and configure email profiles in Outlook
http://support.microsoft.com/kb/829918/en-us
Regards,
Melon Chen
TechNet Community Support
It's recommended to download and install
Configuration Analyzer Tool (OffCAT), which is developed by Microsoft Support teams. Once the tool is installed, you can run it at any time to scan for hundreds of known issues in Office
programs.
Manage computer certificates

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Asked to enter PIN multiple times when sending Digitally Signed emails

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