Because Date.tomorrowtomorrow and Time.nowat UTC also tomorrow.
You will notice that you are doing this in 10:52pm(for example, EST)
but actually 2:52am tomorrow (given the difference -0400)
Thus, as tomorrow there will be no more tomorrow, this is a lie.
If you changed it to >=, it may pass.
As you already found, a workaround is to use the key on .to_time
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