recurring "season' fo the purpose of email triggering

I have defined a recurring 'winter" season with priority 1, from nov 20 - mar 10th. What i am trying to do is to have email that talks about winter driving conditions trigger for any bookings that stay during that period. I do not have any rates defined for this period as rates are handled by other rate periods or default to standard rate. I noticed that email does not trigger even though this season 'winter" is selected. What am I doing wrong? TIA

Seasons can overlap but only one season is selected for each time period in a booking based on the priority. So the long Winter season will never be picked up as the other ones are getting selected first.

Could you associate the trigger with the 3 or 4 seasons in that period instead?

I do that, but that leaves gaps when I have default rates (and those may span into other calendar seasons that are NOt in winter). So what happens is email does not get triggered for calendar winter months if those fall under default rates. I trigger it manually but sometimes I forget :) If I let it go by default all-encompassing season, then summer stays will get an email about winter travel, which I am trying not to do. Anyhow, not a big deal, I just thought maybe I am not using the seasons correctly :)