That sounds like an issue with your own tech department, not Canvas. There is nothing unique about students recording in Canvas and grading it that would be different from any other type of assignment. If your pass back is failing, I'd call Canvas support, but also let your own tech department know.

You do have to be very specific with how you set up each assignment in order for the grades to sync properly with Skyward. Your due dates have to be within the grading period. You have to make sure the assignment is listed under a category that matches what is in Skyward. Duplicating an assignment and then making simple edits to the assignment (like material to record) could cause issues.