Hi Jimmy,
If you lose the other bleed after having dispatched with 1 bleed u/s it will take some time before the cabin reaches 9550 ft or so. Consider cruising with a cab alt of somewhere around 7550 ft, the cabin will start to climb at around 5-700 ft/min (depending on the sealing deterioration) that will give you about 1 min 30 sec to try and reset the bleed and if that doesn't work ask for descent with a PAN initially. You will most likely hit the excessive cabin altitude during your descent especially if you were cruising at high altitude and then you transition to the emergency descent memory items and procedure. If the above happens at lower FL with lower cab altitudes you will most likely not get the excessive cab alt.