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Vlookup / Index disappearing

Apologies if I'm asking a really dumb question, I am somewhat new to excel.

I'm having a problem with a macro-enabled workbook. I have tried both Index and Vlookup, but both formulas just disappear and only leave behind the last value they found. Attached is a massively simplified (and ugly) version of what the spreadsheet is supposed to do.

The issue I'm having is that every time I add anything new into the empty slots of column B, Vlookup completely disappears from the cell it's in and just leaves behind "Item B" or whatever the last value it searched for was. Is this supposed to work this way? I also tried Index, and the result was the same. I don't know how to figure this out without manually re-writing the formula every time the list of items changes, which is a huge pain.

Thanks for any help.

https://preview.redd.it/ceyghyu6t0rg1.png?width=627&format=png&auto=webp&s=1e0a247397d39b1a050841f1ada44b14b8d5fae8

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