Hello,
Have you right to ask for PRRA? If yes you would have to wait 1 year after your judicial review dismissed to filed your PRRA. Meanwhile you can still working.
What I did in this case, was to applied for another open work permit, with a letter to explained to IO that I need to work to take care of my child while waiting for prra, and they renew my work permit for 2years.
Even with 2 years work permit I couldn't applied for permanent job, I steel working in the same place but they will not offer permanence until I become PR.
In my opinion, you must apply for a renewal at least 2 month before your actual permit expire, and show the application then the new permit to your employer in order to extend your contract.
I wish you best of luck! I been in your feet 2 years ago, without any partner to support and i was awful, but I know that it's gonna be alright by God grace.