@PastelSpoonie I could replicate this with modification: in a new folder with settings like yours I made two sims pregnant and waited out the baby time period. The baby was born on a wednesday, and the calendar had an icon for their birthday on the following friday. Friday came and went without baby aging up; and on saturday the birthday icon for the baby had moved to that day in the calendar. They did age up then though. I found some reports saying the same thing, except the moving of the birthday in the calendar.
Is it only the babies that have their birthdays moved in the calendar like that, or other ages as well? Do the days moved vary in number?
A possible solution for your current challenge: I got the notification for the baby's birthday a day before their first birthday (on Thursday); so would not the rules of the challenge permit you to age up the baby when you get the notification/their 'first' birthday appear in the calendar? I don't play challenges, but what I have read of rules so far they seem to forgive any actual game issues. I would advise you do a Save As, in case it turns out to be a bug, and saves are needed.
@PastelSpoonie Great that you are going to test it; and in a new folder with no mods since they can have unforeseen consequences even if it isn't intuitive to their actual aim. I'll be interested to hear about it.
I am guessing this is the challenge?
https://snarky-sims-witch.tumblr.com/post/181535303038/tos-i-am-the-original-writer-of-the-sims-4-version
I interpret the rules to be forgiving for trying to solve problems resulting from game issues; and that toddler's age are not bound by the calendar, but by their skill development. Quote from rules section:
"No cheats! The only exceptions to this are bb.moveobjects on for creative building purposes and cheating to resolve glitches."
And
"Toddlers can be aged up when they reach level 3 in all toddler skills."
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