Twitter has deprecated support for V1 APIs, specifically, you can no longer post tweet with media using the V1 API endpoint. However, V2 APIs dont currently support the upload endpoints yet 
The team at Pathfix has researched and come up with a workaround solve for this until Twitter releases the endpoint support for V2.
Below is the step by step guide on how you can do this using a combination of V1 and V2 endpoints
We are monitoring the API support by Twitter and will update the documentation if there are any changes published by them.
Do reach out to our support if you need any assistance specific to your application.