imessage on macbook pro unable to send files (PDF, JPG, PNG)

I just upgraded to a 2023 Macbook Pro 14" and when I try to send a file via iMessage, it shows as delivered but the person on the receiving end (both Apple and Android) does not actually receive the file.

I had this same issue with my 2012 Macbook Pro but I attributed it my OS being so old. Now that I have this same issue with the most up-to-date OS, I'm not sure what the issue is and it's quite frustrating!

Does anyone have a solve for this?

I've attached 2 screenshots - 1 of files being sent from my imessage on my laptop and 1 on the receiving end of an iphone user.