Hi @bees8, I am so sorry for the trouble. I just gave this a go on my side and was able to reproduce the problem. The Twitter node really needs a big time update, I’ll make sure to add this to our backlog for it.
In the meantime, you could consider uploading your image via the HTTP Request node like so:
This approach worked fine when testing it just now:
Let me know if you have any questions on this.