The answer is AMAZE, five letters. No answer has appeared under this clue more often, with STUN next at four squares and AWE and WOW at three. Every candidate is a verb, like the clue itself, and several of them started out describing something much more violent than surprise.
Astound and stun both come from thunder
Astound, astonish and stun are three versions of one word. All of them go back through Old French estoner, to stun, daze or deafen, to a Vulgar Latin verb built from ex, out, and tonare, to thunder. The literal picture is someone left thunderstruck. Stun, recorded in the early fourteenth century, is probably a shortened form of Middle English astonen, and it kept the physical sense of dazing someone or knocking them senseless.
Astound has an odd shape because of how it was used. It grew out of the Middle English past participle astouned, and one explanation is that the participle was so much more common than the plain verb that it came to be taken for the infinitive. Astonish meant to stun or strike senseless around 1300 and only settled into the sense of amaze in the 1610s.

Amaze meant to put someone in a maze
AMAZE has a different root and a similar arc. It traces to Old English, an intensive prefix attached to the same element as maze, so to amaze someone was, in effect, to put them in a maze. In Middle English amased meant stunned, dazed or bewildered, and earlier still stupefied or foolish. The sense of overwhelming someone with sudden surprise or wonder is recorded from the 1580s, and the adjective amazing picked up its approving sense, wonderful, by 1704.
Surprise words that started as blows
Look down the list and a pattern appears: several of these verbs began as physical violence. FLOOR meant to knock someone down to the floor in the 1640s and was being used to mean puzzle or confound by 1830, which is the sense in I was floored by the news. SHOCK arrived in the 1560s for a violent clash of armed forces, from French choc, and the verb was being used for offending or disturbing people by the 1650s. STAGGER meant to walk unsteadily or reel, and its transitive sense of bewildering or amazing someone is recorded by the 1550s.
Even SURPRISE began in combat. In the late fourteenth century the noun meant an unexpected attack or capture, from an Old French word for taking unawares, and the verb came to mean strike with sudden astonishment only around the 1650s. AWE started in fear: it comes from Old Norse agi, fright, and its early English senses included fear and terror.
That shared history is useful in the grid. When the clue leans physical, with wording about reeling or knocking, try STUN, FLOOR or STAGGER before AMAZE.
Astonishment words by length
| Letters | Answer | Note |
|---|---|---|
| 3 | AWE | Also a noun, a verb here |
| 3 | WOW | Informal |
| 4 | STUN | The usual four-letter fill |
| 4 | DAZE | Shares no square with STUN |
| 5 | AMAZE | The lead answer |
| 5 | FLOOR | Figurative since 1830 |
| 5 | SHOCK | Shares the middle O with FLOOR |
| 7 | STAGGER | Amazing sense by the 1550s |
| 7 | STUPEFY | Starts ST, like STAGGER |
| 8 | SURPRISE | The plain word |
| 11 | FLABBERGAST | A vogue word in 1772 |
Picking among AMAZE, FLOOR and SHOCK
At five squares the three candidates overlap in only one place: FLOOR and SHOCK both have an O in the middle square. An A in the first or third square means AMAZE, an O in the fourth square means FLOOR, and a K at the end means SHOCK. FLOOR has appeared under this exact wording in American newspaper puzzles, so do not dismiss it because it reads like a noun. At four squares it is simpler still, since STUN and DAZE differ in every one of their four boxes.
FLABBERGAST, at eleven squares, is the showpiece of the list. It was noted in a magazine as a new vogue word in 1772, was recorded as a Sussex dialect word by 1823, and its origin is still uncertain, though one guess ties it to flabby and aghast.