The Admiral and I have had some issues getting our anchor to set recently needing several tries to get it done.
We are in the Chesapeake (read: mud) and use a Danforth as our primary. 30 ft of chain and usually at least 5:1 scope
I am on the anchor and the wife is driving. General process is approach drop spot, coast to stop into wind, drop anchor and enough chain to hit bottom plus extra while boat begins to drift in reverse. Typically avoid piling chain on top of anchor.
Trying to narrow down the problem (procedure, anchor drop, driving, anchor type/condition). Would like to set it on one attempt and feel comfortable anchoring in tight quarters. Also, would like to reduce the discussions between anchor person and helms-lady
and not be those people who have attempt a set 4 times.
Once set we usually back down under throttle and are good to go.