Conditional automation condition failing

In the screenshot you posted, the input is "1 week late" when the Otherwise condition fails.

This makes sense as "1 week late" satisfies condition 1, so it should never make it to the Otherwise case with the current test record.

Did you change something about the test record so that it would display as "2 weeks late"?

If so, you need to reload the test record in your Automations window so that the input is "2 weeks late." It should run through the Otherwise condition at that point.

In other words: When you load a test record to test an automation, Airtable loads the record data as is at that moment. It does not watch the record for live updates that change it, and will assume the record is unchanged until it is reloaded.

Aha, okay! So, to be clear: If the test record only meets the first IF test, that test will pass but the second one will fail, so I need to test with a record that meets the otherwise?

The view I'm using as the trigger will only contain records that meet one of the two conditions (contains either "1 week late" or "2 weeks late.")

How do I go about testing if both work? If I go back to the start and choose a record that doesn't meet the first condition (contains "1") but does meet the second (otherwise or contains "2"), my test fails at the first step (which makes sense, since it doesn't contain "1").

Correct.

To test the second step, you need to load a different test record that you expect to fall into the Otherwise condition.