Today I started working a fair. My iPad (that I have used with Square for several years) can log into square. I can enter items, but it does not read or acknowledge that My card reader is plugged in. It is also paired with my chip reader, but will not read that either. I can manually enter charge cards successfully. I updated the app, but it still doesn't work. What is wrong?
It seems strange that neither reader will work. Are they both charged? Have you tried to re-pair the contactless reader in settings on your iPad? https://squareup.com/help/us/en/article/5639
Here are some other suggestions on getting the readers to connect. You could also try completely deleting and then re-downloading the app.
https://squareup.com/help/us/en/article/5673-square-contactless-and-chip-card-reader-troubleshooting
https://squareup.com/help/us/en/article/5412-square-chip-card-reader-tips-and-troubleshooting
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