first time users will likely not have a key pair yet. if they start by using the add-in in outlook, it should be easy for them to figure out how to get one. at a minimum, they should be pointed to kleopatra, ideally with the dialog to generate a new keypair opening automatically if a "generate now" button was used.
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Suggested patch in work/tfry/connect_check_email :
When a web client (first) connects, check whether a secret key matching this account is available. Otherwise, pop up a dialog, with options to open kleopatra or kleopatra --gen-key.