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Tobo's Shadowgate keys were 10 magical talismans created by the young Black Company sorcerer Tobo in Soldiers Live. They permitted safe passage across Shadowgates, and, when combined with training and discipline, allowed transit across the otherwise lethal glittering plain. The keys "looked like four black glass cylinders a foot long, two inches in diameter" and were equipped with silver handles on one end. The new keys, despite their difference in appearance, were functionally identical to older such keys like the Lance of Passion, the golden pickax, and, presumably, Longshadow's lost key.

Tobo crafted the keys using the secrets that he stole from the sprawling library at Khang Phi in Hsien, while several members of the File of Nine were distracted by Sleepy, the Black Company Captain. Tobo commented that they were easy to create once he had the specifications. Whereas, during the preceding 4 years, it proved impossible to reverse-engineer such artifacts even with an older Shadowgate key – the golden pickax – in his possession. The new keys replaced the pickax, which was the ancient Shadowgate key that Sleepy had used in Water Sleeps. After making his new keys, Tobo left the obsolete pickax with the golem Shivetya in the fortress with no name.

The new keys were distributed to trusted members and allies of the Black Company when they began migrating out of Hsien and onto the glittering plain. The first recipients of the new keys were: Blade, Suvrin, Lady, Croaker, and 2 battalion commanders from Hsien. Soon after, Sleepy entrusted the Chu Ming brothers with one of the new keys when they escorted Goblin to the Voroshk world to rendezvous with Croaker, Lady, Murgen, and others.

The keys were subsequently used during all the Black Company's movements across the homeworld and Voroshk world Shadowgates in Soldiers Live. Because the First Father and Nashun the Researcher did not have such keys, they were violently blasted by the homeworld Shadowgate after Tobo repaired the structure. They survived only because of their protective shefsepoken robes.

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