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Hi there, thank you for reaching out to the Paid Memberships Pro team.
This is the intended behavior. The option allows members to hold multiple memberships in the same group but they cannot checkout for multiple levels at a time. This decision was made due to the complexities of reporting and the limitations that many payment gateways have that don’t allow for multiple subscriptions to be created during a single checkout.
Kind Regards,
Jarryd
Support Manager at Paid Memberships Pro