Rest/API for File upload

Hi, @yorambaron.

As I am not familiar with Java, I may not be of much further help, but what about trying the following approaches:
With OkHttp:

OkHttpClient client = new OkHttpClient();

MediaType mediaType = MediaType.parse("multipart/form-data; boundary=----WebKitFormBoundary7MA4YWxkTrZu0gW");
RequestBody body = RequestBody.create(mediaType, "------WebKitFormBoundary7MA4YWxkTrZu0gW\r\nContent-Disposition: form-data; name=\"files\"; filename=\myphoto.png\"\r\nContent-Type: image/png\r\n\r\n\r\n------WebKitFormBoundary7MA4YWxkTrZu0gW--");
Request request = new Request.Builder()
 .url("https://api.hubapi.com/filemanager/api/v2/files?hapikey=my_key")
 .post(body)
 .addHeader("content-type", "multipart/form-data; boundary=----WebKitFormBoundary7MA4YWxkTrZu0gW")
 .addHeader("Content-Type", "multipart/form-data")
 .build();

Response response = client.newCall(request).execute();

With Unirest:

HttpResponse<String> response = Unirest.post("https://api.hubapi.com/filemanager/api/v2/files?hapikey=my_key")
 .header("content-type", "multipart/form-data; boundary=----WebKitFormBoundary7MA4YWxkTrZu0gW")
 .header("Content-Type", "multipart/form-data")
 .body("------WebKitFormBoundary7MA4YWxkTrZu0gW\r\nContent-Disposition: form-data; name=\"files\"; filename=\"myfile.png\"\r\nContent-Type: image/png\r\n\r\n\r\n------WebKitFormBoundary7MA4YWxkTrZu0gW--")
 .asString();