Abstract: Automated delivery coordination and meeting scheduling for an order including a plurality of recipients includes identifying, by a computer, an online business transaction performed by a user. The online business transaction including the order being placed by the user for the plurality of recipients. The computer determines whether the order is associated with an event that includes the plurality of recipients and, in response to the order being associated with the event, collects information corresponding to the event. The computer uses the collected information to generate a first recommendation during checkout including a synchronized delivery option for the plurality of recipients. Further, using the collected information, the computer generates a second recommendation during the checkout including a synchronized meeting scheduling option for the plurality of recipients.