New Computer Cannot Open Old Encrypted Emails

I have a user that has recently been set up on a new computer copying their .pst from an older system.
The previous computer was running Windows 7 32bit w/ Office 10 and the new one is running Windows 7 64 bit w/ Windows 10.
The user can open recently received encrypted emails but cannot open emails prior to the date they were moved to the new system. I have removed and reinstalled their credentials and exported them as well but to no avail.
Any suggestions on recovering access to encrypted emails prior the creation date of their new profile on the new computer?

Was the "old" Digital-ID installed/ imported into Outlook after setting up the new workstation?
Mostly the reason for such behaviour would be missing private key matching the public key the messages were encrypted with. You won't be able to decrypt the mails without it.

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