The Masked Stranger is a mysterious figure who was conducting archaeological research on Reaper related artifacts. She rescued newfound "lover" Stitcher Jim from being marooned in The Devil's Roar. She and Jim joined the Bilge Rats and started preparing a fortified base at The Reaper's Hideout. After the completion of the Hideout, the Stranger disappeared, but there are some who rumour The Servant of the Flame who took her place to be her.
The Masked Stranger first appeared with Jim during Smuggler’s Fortune at the Uncharted Island now known as The Reaper’s Hideout. She was working on deciphering the contents of Reaper’s Chests and creating sketches of a chalice, a dragon figurehead, and of Shipwreck Bay.
Later, through The Fort of the Damned, she and Jim moved to Castaway Isle to keep a close eye on Old Boot Fort, which had just transformed into the now Fort of the Damned, where the Ghostly form of Graymarrow was released with a Shadowy Ritual.
With the The Seabound Soul, their planned ritual at Shipwreck Bay was completed, releasing the Ghost of Sir Arthur Pendragon from his curse. This set Pendragon on a mission to enlist pirates with the task to release the souls of other cursed Captains, which lead to the accidental releasing of Captain Flameheart whose soul had also been cursed. During all of this, Stitcher Jim was at Taverns, filling in for Duke as the Bilge Rats representative, while the Masked Stranger worked away behind a locked door within Wanda’s Hideout on Wanderers Refuge.
Coming out of hiding for Festival of Giving, she charted the previously Uncharted Island at I/J-12 and named it The Reaper's Hideout. There she took residence on the South-Eastern island, dressing it up for the festive season, and began collecting Gifts from passing Pirates. Construction continued through Legends of the Sea, with a Fort erecting around the South-Eastern island, while The Masked Stranger accepted various of the more valuable Trading Company Treasures for double their value.
In the Heart of Fire Tall Tale, Stitcher Jim's carvings in the walls of his hidden Hideout at Liar's Backbone indicate that the Masked Stranger is Captain Warsmith. Additionally, the Stranger can be seen overlooking Stitcher's ritual during the Tall Tale.
No dialogue was available.