Regarding the first issue mentioned by @konat1993 , in case anyone have it: we had a similar problem and the solution was: to increase the RAM memory of the instance running Strapi. Additionally, if the file is larger than 100MB, you must ensure that your Cloudinary plan supports uploading larger files (More information here https://support.cloudinary.com/hc/en-us/articles/202520592-Do-you-have-a-file-size-limit#:~:text=Please%20note%20that%20uploads%20of,files%20without%20using%20chunked%20uploads.).
On the other hand, for the issue raised by @lozcozard , we still currently have the same difficulty with Strapi 4.20.0 running in Heroky. We encounter a timeout error when uploading “large” files (150MB approx), which is caused by the maximum time supported by Heroku during the upload process. Has anyone found a way to solve or workaround this?