Attaching documents to COBRA benefit enrollments You can add benefit enrollment-related documents on behalf of a COBRA participant. Select Benefits > Maintenance > COBRA Participant > By COBRA Participant. Select the COBRA participant. Open a benefit plan to attach documents. You must open a benefit plan with a Current or Future time frame.See Opening benefits by COBRA participants. Attach documents to COBRA participants in the benefit plan: Click the Documents tab. Click Create from the Attachments list. Click the folder icon. Select the file from your local folder. Click Open. Click Save.