The Harold Lloyd Insurance Union (ハロルド・ロイド保険組合, Harorudo Roido Hoken Kumiai), also called Harold Lloyd (ハロルド・ロイド, Harorudo Roido) for short, is the Bentenmaru and the Barbaroosa's insurance company, one of the largest in the Orion Arm , and a frequent job provider for the pirates.
Harold Lloyd is one of several insurance companies that provide jobs for pirate ships, such as the Bentenmaru and Barbaroosa . As such it conducts negotiations with the parties involved regarding arrangements for the jobs in question and decides whether to approve them . They also deal with the insurance for items stolen during liner 'raids' .
- Mark's Intelligence System (マルクス情報システム) 
A few years before the start of the series, Show took over from Harold Lloyd as the company's primary agent .
Hakuoh Pirates ArcEdit
When Jenny Dolittle fled to the Bentenmaru to escape her arranged wedding, Robert Dolittle had Hugh and Dolittle Interstellar Transportation put pressure on Harold Lloyd to have her handed over to him, threatening to cut ties with them if they didn't. After speaking with Jenny, Show agreed to let the Bentenmaru take the job of escorting her to the safety of Space University rather than giving in to Robert's demands, accepting the terms and payments she proposed, including 10% of the annual profit from her company Fairy Jane .
Abyss of HyperspaceEdit
During the spring break before Marika's third year at Hakuoh Academy, Harold Lloyd was losing a fair number of jobs due to a series of subspace accidents and other occurrences in the market, which was later revealed to be the work of the Yggdrasil Group. During the search for Professor Mugen's legacy, Harold Lloyd hired Ririka to act as a bodyguard for the Bentenmaru crew, lending her a Silent Whisper for the job .
- The company and its former owner are named after Harold Lloyd, a famous actor in silent comedies.