AVAIL, five letters, answers the benefit crossword clue. It carries the verb sense of being of use to someone. Shorter slots switch to the noun senses and give PERK, BOON or GAIN at four, while a fundraising reading in the surface wants GALA instead.
Avail survives in exactly two places
You will almost never hear this verb standing on its own in American English. It lives inside two constructions and essentially nowhere else. The first is reflexive: you avail yourself of an offer. The second is the fixed negative, to no avail, where the word has quietly become a noun. Nobody says the effort availed him any more, though that was once perfectly ordinary.
Words in this condition are sometimes called fossil words, meaning they are alive only inside a phrase that carries them. English holds on to a fair number. Fro survives in to and fro. Shrift survives in short shrift. Kith survives in kith and kin, dudgeon in high dudgeon, beck in beck and call, bated in bated breath, wreak in wreak havoc. Lift any one of them out of its phrase and most fluent speakers cannot define it.
BOON, the four-letter neighbor on this clue’s list, is partway down the same road, surviving mostly as a boon to something. GAIN and PERK are in no such trouble and remain fully current. Puzzles are one of the last places the fossils still circulate on their own terms, which is how regular solvers end up with a working vocabulary that has otherwise left the language.

Benefit is doing three jobs at once
As a plain noun it means an advantage. In the plural and in a workplace setting it means the non-salary part of compensation, the health coverage and retirement contributions and paid leave, which is a distinct sense with its own conventions and its own paperwork. As a noun it also means a fundraising event, as in a benefit concert, where the word has slid from the advantage itself to the occasion that produces it. And as a verb it means to be of use.
British usage adds a fourth. On benefits means drawing state welfare payments, a sense American readers mostly meet through imported television. A puzzle with a British flavor can want DOLE at four letters for it, which makes no sense at all under the American reading.
One word, four senses, three parts of speech, and a clue that hands you nothing but a square count. That is the whole reason this entry is harder than its bland surface suggests.
The fill list, slot by slot
Work from the square count down, then check the sense against whatever the surface is hinting at.
| Length | Fill | Sense being clued |
|---|---|---|
| 3 | AID | The helping sense, very short slots |
| 4 | PERK | Workplace compensation |
| 4 | BOON | Something welcome |
| 4 | GAIN | The plain noun |
| 4 | GALA | The fundraising event |
| 4 | DOLE | British welfare reading |
| 5 | AVAIL | The verb, be of use |
| 5 | ASSET | A loose synonym, easy grids only |
| 9 | ADVANTAGE | Long slots, the literal definition |
Signals that tell you which sense is meant
Tense comes first. A surface reading benefits or benefited is asking for a verb, and that alone eliminates most of the list. Register comes second: any mention of a concert, a gala, a charity or a fundraiser has switched you into the event sense, and late-week puzzles lean on that reading precisely because solvers reach for it last.
Abbreviation markers come third. A clipped word in the surface, or a tag such as for short or briefly, changes the register entirely and can pull the answer somewhere you were not looking. If AVAIL, PERK and GAIN have all failed against your crossings, the mistake is almost certainly in which sense you picked rather than in the crossing entries themselves.