Using the anchor trolley
The way I find best, is let out some anchor rope first (enough to go to the bow and back) and then clip it through the shackle on your anchor trolley, then set the anchor trolley to the bow or the stern so that when you drop the anchor over the side your anchor trolley and the anchor will be in the correct position for you let out the anchor rope. Once the anchor has set on the sea bed and you are not moving, it is at this point we tie off the rope or grip it with a cam cleat/clam cleat. How much rope? This will all depend on the depth of water, the tide run and the sea bed. In shallow water you may only have to let out 3 times the depth you are in or you may have to let out up to 10 times the depth in deeper water, but you most remember to let out enough to hold you in position and allow the kayak to ride the swell. Some kayakers use a short length of chain to help the anchor to set and hold bottom but I’ve never use any chain on my 3.5lb anchor I find the tide pushing on the anchor rope creates a bow in the rope that lessens the angle of the rope, this helps the anchor to hold bottom. I have had 4 kayaks tied to the back of my kayak using this method and it kept us all in position. See fig (2) & (3) for bow and stern anchoring.
Retrieving the anchor
When using an anchor trolley there is no need to release the anchor trolley to pull up the anchor. As you pull on the rope the kayak will want to be pulled towards the anchor and the water can come over the side of the kayak. Another good reason for not retrieving from the side is that if a stuck anchor does pull loose all of a sudden as you are pulling hard you could end up going out of the kayak on the opposite side. The way I retrieve the anchor is to leave the trolley locked so it can’t move, then all I do is pull the anchor rope towards me is give me the maximum leverage I can get when the anchor is stuck. Once the anchor is free and you are pulling in the rope I find it best to retrieve all the rope at once, I do this by letting the retrieve rope go back over the side of the kayak (same side as the trolley), the tide will take it away from you to start with but once you are drifting you will drift at the same speed as your rope. Once the anchor has come up to meet the trolley you can do two things, leave it at the end of the trolley and lock it off with your cam cleat or release the trolley and pull the anchor in the kayak. The good thing about this way is that you can move away from any danger quickly and it is a lot easier to coil the rope on your spool as you are not lifting the anchor with every wind. If your anchoring from the stern and the anchor is stuck then all you have to do is back paddle up tide until you have enough slack on the anchor rope to move the trolley to the bow, and then try again.