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After several of the Chaos Emeralds disappeared, Tails teamed up with Knuckles to set a trap for them. Reluctantly, he took apart his prized Tornado and rebuilt it into a trap. The thieves soon appeared and sprung the trap, but proved able to break out of it. Tails then watched in horror as Knuckles engaged the attackers only to be defeated by their leader and dragged off. Realizing that he couldn't handle this problem alone, he set out to get help from Sonic, Amy, and G.U.N. (StH: #191)
The Wisps and the Time Eater
After learning about an amusement park built by Dr. Eggman, Tails and Sonic went to investigate it. Upon arrival they met Yacker, one of the Wisps, and saved several of his friends from Orbot and Cubot. Some time later, Tails attended Sonic's birthday party along with the Chaotix, Rouge the Bat, and other friends. However, the happy gathering was interrupted by the attack of the Time Eater, who created portals to draw Tails and Sonic's other friends to times and places unknown. (StH: #219, #230)
Other Worlds and Crazy Games
Tails later teamed up with Sonic to investigate the return of the Little Planet, and was treated to Sonic's musings on his previous adventures there against Metal Sonic. Shortly thereafter, Tails competed in the Olympics, and was taking part in an event with Sonic and Shadow when Dr. Eggman attacked with a giant Caterkiller that captured Tails. Fortunately, Sonic was able to rescue him and the other trapped competitors. Another time, he took part in a contest with Sonic, Amy, and Knuckles to see who could collect the most Red Rings. (StH: #242, HFCS: #1, SSSM: #3, #10)