I only want this automation to run if the the 1 day before checkin date is hit and if status is either “Pending Action” or “Contacted” not both status. Does this mean on this setup on the screenshot, it will only run if the status of the item is both “Pending Action” and “Contacted”. I know there is only one status per item but the the phrase “and only if” confuses me. Just new to monday.
Hey Jay, for the recipe you shared, it will only be triggered if the Status is “Pending Action” and “Contacted”. It’s not an “or” condition, but an “and” condition, meaning both criteria need to be met.
However, in your case, it seems that the recipe is linked to the same Status Column. Therefore, this specific recipe will never run because it’s not possible for both conditions to be met with this set up. The option to add multiple “and only if Status” conditions is intended for boards with multiple Status Columns.
To achieve what you’re looking for, you’ll need to set up two separate recipes. One recipe should have the condition “and only if Status is Pending Action”, and the other recipe should have the “and only if Status is Contacted” condition. I hope this helps! 
Thank you Malia. Tha clarifies it.
You’re welcome, Jay! Happy to help!