You can try it yourself easily:
Post a tweet that links, say to the front page of the dailymail.co.uk
Take a snapshot of that tweet, incl. the image twatter produces automagically via the link you've posted.
Check tomorrow, after frontpage of dailymail has changed, and the looks of your tweet will have changed as well.
>/uploads/053020_
>Still looks uploaded on 5-20-2020
If not a typo, then that'd be tard jail for you, I guess. Kek!
>nor how close the first found date matches up with the actual post date
Wasn't able to find exact numbers on their "turn-around", but it can probably take a couple of days, likely depending on some page ranking.
Given the floyd image apparently was uploaded 05/30, 1st of June is pretty close.
https://tineye.com/faq#why_cant_find