IMO it was at arrival. There's not much to go on, other than Stanley Armour Dunham's age:
Arrival was supposedly June, 1959. (Three months before the FIRST AIRLIFT OF KENYAN STUDENTS)
The on the beach image would be around 1963? Does Stanley Armour Dunham appear to have aged some 4-5 years?
The photo of Stanley and 0bama on the beach looks later; the kid looks about 4 or maybe even 5. He’s tall, and kids that age can vary in size when they are destined to be tall.
I’d say 4 1/2 maybe.
So, if that is correct, Stanley would be at least - well, I can’t say, because who knows if the 1961 birth date is accurate. But he certainly looks quite a few years older.