Answers to the clues:
- Row (02): issue, lap up, ubuntu, cayenne, days, wind sock, idyll, crinkled, Finn, midfield
- Row (04): root canal, orcs, echo, Earp, clip art, sample, elapse, web games, Dinah, horizon
- Row (01): Boulder, counter, dilute, small fry, mortar, roasting, paradigms, Cadillacs
- Row (05): used up, pâté, guilty, esprit, friars, senior, pled, Zappa, Iowa, Oahu, Olds, shlep
- Row (03): crewel, parasol, pilcrow, deuce, big-eyed, sighted, diphthong, peasants, wisp
As implied by the flavortext, one can read the solution DUSKY SHROUD along the diagonal.