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Q: Can guest checkout be configured to only be enabled if a customer has certain products in their cart, and require login if they have product A in their cart?
A: Currently guest checkout is all on or all off. We are evaluating this as an enhancement for 2021.
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How-to Guide of this page can be found here: [Internal] Common Troubleshooting Setup Guide
Real Example of this page can be found here: Common Troubleshooting: Age Rules