Tegh25 commented on PR #68359:
URL: https://github.com/apache/airflow/pull/68359#issuecomment-5147956508

   @uranusjr it is an intentional design choice.
   
   `on_skipped_intervals_callback` / `on_intervals_skipped` are meant to report 
a gap between two automated Dag runs. Detection is anchored on the previous 
automated run’s data interval. If there is no previous automated run (brand-new 
Dag, or first schedule after unpause with nothing in history), there is no gap 
to summarize, so the hook does not fire even when historical intervals from 
`start_date` are never created.
   
   So in your example, with catchup=False from the start (or after flipping to 
catchup=False with no prior run to compare against), January-June are simply 
never scheduled. The callback is for later skips (paused Dag re-enabled, 
scheduler downtime, etc.), not for “everything before the first run.”
   
   I’ve now documented this explicitly in the Skipped Intervals sections of the 
callbacks and listeners docs (and briefly in the on_skipped_intervals_callback 
docstring) so the behavior is noted.


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