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Can a Skip card be played before all the players have had at least one chance to play? Or can it be played at anytime?

2

There is no such restriction. From the rules:

The player ends the turn by discarding one card of choice onto the discard pile.

And

SKIP CARDS: When discarded, a "Skip " card causes another player to lose their next turn. The player who discards the "Skip " card chooses the player who loses their turn. When a player draws a "Skip " card, the player may discard it immediately or save it for a later turn. A "Skip " card may never be used in making Phase 8, or any other Phase. A "Skip " card may never be picked up from the discard pile.

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  • 2
    In fact, the game can play a Skip card before anyone has had a chance to play: "If the dealer starts the discard pile with a "Skip" card, the first player's turn is automatically skipped." – Benjamin Cosman May 21 '16 at 22:50

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