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Do I need to check a category for every transaction on my statement?

No, you should only use a category when your purchase fits the description for that category. For more information, see page 10 of the ProCard Reconciliation Quick Reference Guide.

I only see one purchase listed on my statement but I made several purchases within the billing cycle that I am reconciling.

PeopleSoft is set up to show the first line only under transactions. Click view all under transactions to see all of the transactions/purchases.