While the dough can be prepped entirely by hand, using a KitchenAid Stand mixer with a dough hook will speed the process. Dissolve yeast and 1 tablespoon sugar in 1 cup lukewarm water. (Make sure the container is a little larger than 1 cup in size as the yeast will foam up). Scald the milk (heating to just below boiling point) and add butter, ½ cup sugar and salt. Allow the mixture to cool to lukewarm. Pour the milk mixture into a large mixing bowl and add 2 cups of flour to make a batter. Add the yeast mixture and beaten eggs, beat well. Add the remaining flour slowly or enough to make a soft dough. Knead lightly and place in a greased bowl. Cover with a clean tea towel and set in a warm place, free from a draft. Let the dough rise until doubled in size, approx. 1 ½ hour. When light, punch the dough down.
Note: The amount of flour can vary each time this recipe is made due to humidity and other factors. After the 5th cup of flour is added and incorporated, add the remaining flour ½ cup at a time, and stop once the dough is silky and no longer gummy. Adding too much flour will cause the dough to be dry and possibly reduce the ability for the dough to rise.
Divide the punched down dough into 3 equal portions. Round up each portion and roll out into oblong pieces approx ¼ inch thick. Brush with melted butter and sprinkle with brown sugar and cinnamon evenly across the surface. Sprinkle the raisins evenly over the surface along with evenly spaced cherries and crushed pineapple. Roll each piece as for a jelly roll and place in a circle, inserting the one end into the other end, on a parchment lined baking sheet. With a sharp knife, cut 1 inch slices almost through and turn each slice partly on its side, pointing away from the center. This will expose the different layers.
Cover and let rise in a warm place for 45 minutes and then bake at 350 degrees for 25 to 30 minutes.
Make a glaze by stirring in the vanilla into the confectioners sugar. Slowly add water, drop by drop and stir until a glaze mixture is created. If it gets too thin, add more confectioners sugar. While the tea rings are still warm, drizzle the glaze over each tea ring.
NOTE: Baked tea rings freeze well. Simply place the cooled tea ring into a freezer bag and store up to two months in the freezer. Allow to thaw at room temperature and serve!