Data Transfer Services (DTS Job) question

I am a caretaker for a SQL Server DTS job that runs daily (per weekday)
The problem is, it is saying succeeded, but “last run status” date does not update and it is a daily weekday ran job. Instead it keeps displaying a 9/15/2019 date.
This job has two “sibling jobs, identical to it, and they do show a last run date of yesterday.
This job does a Drop table, Create Table and Copy Table on multiple tables,
And when I manually run it runs fine. It fear it might not be executing on its own. Also, whenever we run a the job manually, that run timestamp is not tracked by the software, and does not register a “last run timestamp~~the last run date is not updated.
I see where I can change the time of night which it is ran.
I would like to know how I can test its settings to get it back on track?
Thanks for any info!

Look at the schedule for the job. Maybe it is set to start running on 9/15/2019. If so, just move the date back to 3/27/2019 and it should start running tomorrow on its own.

Also, just to be sure, check that the job is enabled and that the schedule is enabled.