Yes, that's always an issue for us: did we put enough chain when we dropped the anchor? I'm the one of the two of us who drops the anchor and makes sure it is fix and holds.
It's easiest when anchoring freely in a bay. Pay attention to the type of ground, sand or silt are good, on sea grass the anchor often digs in badly, rock - that doesn't work at all. The depth of the water, the distance to the shore or to individual rocks and other boats, wind strength, all this has to be taken into account before the chain runs out.
As a general rule, it's better to put in more chain than too little. We have 100 metres. So far we have used up to 60 metres. But it's a good feeling when there are still 40 metres in the box.
Sometimes it's difficult when we lay with the stern to the pier in the harbour in front of bow anchors. That's the case in almost every Greek city harbour, so almost always. What is the ground like in the harbour? What is there on the ground? Maybe a thick ground chain across the whole harbour, like in Ios Port? 30 metres away from the pier. Where are the anchors of the other boats? How many metres of chain can I put in at most? Fortunately Walter, who is at the helm during the harbour manoeuvre, drives around slowly and calmly so that we can look at everything in peace. Hectic is not helpful, but experience and patience are. In the meantime, we've gained in patience. Nevertheless, there is sometimes tension. Once - on Euboea - the anchor winch wouldn't work when I wanted to let the chain out. The contacts in the push-button were completely corroded. Luckily we were able to moor alongside and fix it.
It can also be exciting when retrieving the chain, if another boat's chain is lying above ours and we bring it up with our anchor. We have already been lucky and got rid of the foreign chain by manoeuvring back and forth. But sometimes there is real work to do: pull up the other boat's chain until you can pull a line under it, then fix the line, lower your own anchor again and as soon as it is free, pull the line out from under the other boat's anchor chain. Sounds simple and has always worked, but afterwards I was always nearly knocked out.
In Ios Port, we watched a boat that had deployed its bow anchor later drift alongside onto the pier in strong winds because the anchor had broken loose. Could have, would have ... more anchor chain? Who knows? Our anchor had also slipped sometime, so that we came closer to the pier with the stern. Then it's good to have a few more metres of chain to pull in.