How do we know if our connection with our Shaykh is sound?

Answered by Sayyidi Habib Umar bin Hafiz (may Allah protect him and benefit us by him).

The signs that your connection is sound are:

a keenness to follow his teachings and emulate him;

a feeling of ease and contentment when you hear his qualities and instructions being mentioned

witnessing that he is the door to closeness to the Best of Creation ﷺ and to attaining the pleasure of Allah.