collinmcnulty opened a new pull request, #41558:
URL: https://github.com/apache/airflow/pull/41558

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   The first run behavior for cron based DAGs (and most DAGs really) is quite 
unintuitive. It is very common for users to want to run a DAG for the first 
time either immediately, with a logical date of the past run that would have 
occurred most recently, or to wait until the next run time and then begin. The 
former is only possible is you set catchup to False and the latter is not 
possible without knowing ahead of time when that next run would be and 
hardcoding the start time for the DAG (which is not feasible when doing 
dev/text/prod environment promotion of the same DAG file). 
   
   It is also very common to set the start_date to a dynamic function that 
calculates a date in the recent past, such as days_ago(1), which can bite you 
if you're used to doing that (or have coded it into a DAG factory pattern) and 
then you set up your first monthly DAG. The existing timetables behavior is to 
silently miss the run, which makes it even worse.
   
   This PR adds the ability to set start_date to `None` and get the intuitive 
behavior of running the last run if that run would have happened in the very 
recent past (10% of the distance between DAG runs) or to wait for the next run 
otherwise. It also allows using the `run_immediately` parameter to specify 
always running the last run, always waiting for the next run, or passing a 
timedelta to exactly control what "recent past" means for this particular DAG. 
Setting start_date to `None` is a much more accurate and clear indication of 
author intent that `days_ago(x)`.
   
   I hope that if this is widely adopted, we can stop seeing users miss DAG 
runs or using dynamic start dates.
   
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