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Why wasn't I able to use the first visit $10 off promo. It never worked? How does that get resolved?

When I originally joined Dog Vacay we were unsuccessful to find a sitter that could work with our time frame. So, fast forward 2 months and I again looked for a sitter for upcoming trips. When I did lock in a reservation, the system never accepted the First Time user promo code. Will that be something I can use retrospectively?

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I'd suggest you call customer service and let them know. If this is your first service booked, it seems likely that they could apply the promo code.