Are you installed the Cheat Menu plugin? if you are you can check (or change) a certain 'value' for a specific scene to trigger (Yes, some 'value' indeed connect to another 'value' so if you don't know what your doing best to leave it alone). but in your case I believe your 'job' value should be '1' (1 after you take the 'medicine' job, 2 before you take the job). So, to put it simply your 'value' should be 'job 1' & 'medicine 1' , different that that it maybe the cause of your bug
Tried that, both are at job 1 and Medicine 1.
When trying to deliver the medicine the mc just ask if there is a new job, as if I didn't already asked that.
The quest timer goes e few days forward, when taking the quest waiting until then I can just take the quest again.
On the discord the bug was first reported 2019 I believe, and dev has never responded to it.
What I could gather is that it happens when you have the medicine quest active and you then get the parcel to Adrianna.
Some hidden parameter not shown in the plugin is hindering solving the issue.
Tried changing job to 2 before taking the job, didn't solve it.
But thank you for trying.