Tipping for a hotel room upgrade—often called the "Sandwich Trick" when slipping a bill between your ID and credit card—is a nuanced art rather than a fixed rule. In 2026, the standard "handshake" tip for a front desk agent in the U.S. remains $20 to $50, depending on the length of your stay and the caliber of the hotel. In luxury resorts, a $100 bill is more likely to secure a high-value suite. If the agent successfully secures a significant upgrade that would normally cost hundreds more per night, it is a "pro-tip" to show your appreciation at that moment. However, be aware that many modern hotel chains now use automated inventory systems that prevent agents from giving away rooms for free. If you are offered a "discounted" paid upgrade, a tip is not required, but for a purely "discretionary" upgrade, a polite inquiry accompanied by a discreet cash gesture remains a widely recognized way to signal that you are a "V.I.P." guest.