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Cassian knew the Kirammans as family friends, professionals and counselors. They only started working more close knit once Caitlyn showed interest in becoming an enforcer, shortly after the death of Grayson.
Once Cassian became a student full time, for the better part of 2 years, working closely with Jayce, there was a personal deal brought forth when the Kirammans began funding Jayce's studies. Regardless of the hierarchical status of the Kirammans, and what Cassandra's seat at the Council means to them, he respects her. She sees the danger in being an enforcer, and that they could agree on. He didn't want to let them down; it only encouraged him to assist Jayce even further, before he was pulled from the Academy of course.
Cassian's relationship with the Kirammans was further from estranged after Cassian graduated from Cadet school.
Cassian barely got to know Caitlyn before he was sent to Cadet school, but from what little time he spent with her, Caitlyn admired him admittedly. As a sheltered little kid of a high house, she set him as an example, to herself. In the same way she admired Jayce, she saw him as one who persisted despite the fascinatingly unfair realties of their fine city. As brash and inconsiderate as her pestering was, she couldn't help but ask him, "How do you bother going down to the Undercity with Jayce when you know they killed your brother?" and Cassian couldn't help but laugh at her absurdity.
"It wasn't their fault." He'd remind her, but refrain from saying anything else out of fear of rambling on and on about things she shouldn't hear.
When Cassian returned to the Academy to assist Jayce with the company, Caitlyn told him she was thinking of becoming an enforcer. It's safe to say he tried to talk her out of it, but he could see how persistent she was. He respected her, the same way he respected her mother.