Turns out, Cucumber::MultilineArgument::DataTable#diff! caches some stuff. Code of the following form will not work as intended:

Then('some table should look like') do |expected_table|
  patiently do
    actual_table = calculate_actual_table
    expected_table.diff!(actual_table) # not actually patient, will keep failing if it failed the first time
  end
end

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Instead, simply use

expected_table.dup.diff!(actual_table)