Still not sure what's causing this problem, but one of the things that (after re-)reviewing your post was this:

There is a cron job set to run every weekday at 2:15 a m to kick of several list mailings, including the student list (plus one at 3:15)

I wonder if you hit upon a problem with the scheduler, where it needs perhaps at least one check before it kicks off a mass mailing from a schedule If it doesn't get that, it may be just that it takes the safe bet that it missed the first schedule in the range, and will only start on the second

Personally, if you can, I'd go with running the cronjob much more frequently - I do design things to be checked every few minutes or so

The other suspect thing I found is in the code This line in, dada/DADA/MailingList/Schedules pm:

https://github
com/justingit/dada-mail/blob/master/dada/DADA/MailingList/Schedules
pm#L158-L165

for(@$recurring_scheds){ 
            if(
                     $_->{ctime} >= ($t - 259_200) 
                &&   $_->{ctime} <= ($t + 259_200) 
            ){ 
                push(@$schedule_times, $_->{ctime}); 
            }
        }

I'm hand-waving over a bunch of things, but basically Dada Mail figures out the correct range of dates to send out a recurring schedule, then these lines above find the dates that are near the current date "259_200" is seconds, which is around 3 days I'm wondering, since you're schedule only happens once a week, you're not getting the best feedback on when things should be sent out - which is why you don't get a printout of when schedules will be sent in the future Just a guess I've bumped this, "259_200" to, "604_800", which is a week-full of seconds I've also tried to play with the formatting of this report, so it may make a little more sense, when you look at it You can see these changes in,

https://github
com/justingit/dada-mail/commit/c17be4c1912ad30c542ec7ccac31c7ee27626efb

Bug,

https://github
com/justingit/dada-mail/issues/553