My sister was having a problem where she was taking all the iCloud storage for our family because she keeps sending videos to people but couldn't figure out a way to efficiently delete them. I had to write up a Python script (https://gist.github.com/saagarjha/615dee3c04e226b44828e910a5...) to scrape the iMessage database for large attachments, and then print out the text to messages around it so that you could search for it and jump to around that place in the chat history and then delete the files from there. It's kind of insane how hard it is to manage old messages :/ I feel like Apple didn't really prepare for Messages coming in from iCloud meaning that every device had every single message you've ever sent, and now it's really hard to get through them without reading the database manually…