How did a gratuity given to a serving person come to be called a tip?

Tip is underworld cant meaning to pass on, to hand to, especially to pass on a small sum of money. The ultimate origin of the word is not known. It may come from the sense of tip meaning to lightly touch someone, but this is by no means certain. From Samuel Rowland’s 1610 Martin Mark-All:

Tip me that Cheate, Giue me that thing.


Tip a make ben Roome Coue, Giue a halfepeny good Gentlemen.

The sense meaning to give a small sum of money, appears at the beginning of the 18th century. From George Farquhar’s 1706-07 The Beaux Stratagem:

Then I, Sir, tips me the Verger with half a Crown.

The noun appears about a half-century later. From J. Barebones in The Connoisseur No. 70. of 1755:

I assure you I have laid out every farthing...in tips to his servants.

The idea that it comes from an acronym for to insure promptness is just plain wrong.

(Source: Oxford English Dictionary, 2nd Edition)

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