Older Mails that have been encrpyted with S/MIME before GpgOL was installed don't get the updated Lock Symbol, when S/MIME is activated in GpgOL.
{F207945}
As you can see in the screenshot this account has some older S/MIME encrypted mails in his sent folder and some newer encrypted ones. The ones I sent with the freshly installed GpgOL have the correct Lock Symbol next to it, the ones that were already there don't have the correct lock symbol.