Product Upsell and Customer Specific Pricing

If a product with customer pricing is used as an upsell offer, the customer pricing variants will not show for a regular customer. However, if a regular version of a variant is selected to be upsold that has a customer pricing version as well, the customer pricing version will not show if someone eligible for it triggers the upsell.

In order for a customer pricing variant to show, it should be selected as the upsell item instead of the entire product (or regular variant for that matter). If you don't want a regular customer to have access to that variant, have the trigger item a customer pricing variant that a customer pricing customer only would have access to.