Looking at the images you can see cracks at the edges and low spots in the Pitch Pocket Sealant.  Preventive maintenance could have solved this before it became an issue.  When flashings such as pitch pockets are allowed to degrade to this degree water can enter the building and cause extensive damage.  Call or send us a message.  We can do a free inspection to let you know how we can help extend the life of your roof through preventive maintenance.