Answered by Sayyidi Habib Umar bin Hafiz (may Allah protect him and benefit us by him)
What things would constitute the seeker breaking the covenant with his shaykh?
These things would constitute breaking the covenant:
Being content to contravene the Sacred Law
Showing enmity or having hatred for any of the pious slaves of Allah
Having contempt for the Sacred Law or the Spiritual Path (Tariqah)
Having contempt for any of the affairs of Allah, His Messenger ﷺ or the next life
Having bad thoughts about the Shaykh which the seeker then believes to be true
If the seeker breaks his covenant with his shaykh is it possible to rectify the situation?
The seeker has no option but to return to Allah. He may rectify the situation by making tawbah as long as he is not in the throes of death and as long as the sun has not risen from the West. Cleary someone who breaks the covenant and then makes amends is not the same as someone who has not broken it in the first place.