Attempting push on git and receiving “could not read Username for ‘https://github.com’: terminal prompts disabled”

Question 1

As per my comment. You can include your username in the remote URL (similar to FTP).

Example without password (SSH):

git remote set-url origin git@github.com/username/repo.git

Example with password (https)

https://name:password@github.com/username/repo.git

Source: Git push requires username and password

Updated 5/14/2018 to correct github.org to github.com in the original answer

Question 2

Check that Windows does not have a pending update. If it does, update and restart.