Trouble checking into a business on reoccurring visit

When revisiting and establishment I’ve already been to, I’m sometimes unable to check in again. I’ll be sitting inside the restaurant and it’s showing on ,asp as normal but the “check in” button does not appear, all I see is the timeline including the last time I was there.

I’ve struggled with this for years and am finally remembering to ask. Hopefully someone can help, I enjoy checking in multiple times to add my visits to my timeline for reference.

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