Story highlights Taylor Swift sends a fan $1,989 to help with her student loan debt

She also sends a custom-made painting, even though "I'm not a good painter"

Swift has a history of surprising fans with care packages she assembles herself

(CNN) For a pop star with millions of frenzied fans, Taylor Swift does a pretty good job keeping tabs on them.

She has a history of stalking -- er, "Tay-lurking" -- fans on social media, figuring out their likes, dislikes and what's going on in their lives. And she loves to shower super loyal ones with some enormous gifts

But the package that Rebekah Bortniker received may be one of the most complicated presents yet.

The giant box, labeled "SwiftEx" instead of "FedEx," contained so many meticulously wrapped gifts that it took Bortniker several minutes to open them all.

"Hi you. I was thinking about you today, and how you have been there cheering me on in the most thoughtful and creative ways," the singer wrote on a card.

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