Gin seems especially interested in the boss ' order to hunt for the escaped Shiho, while she is unusually terrified of him.
Ai Haibara 's greatest fear is being caught by the Black Organizationand she is especially terrified of Gin. It is strange that Pictures sex teens and Shiho seem to know a lot about one another despite being in entirely different divisions of the Organization.
They clearly have a connection outside of their professions to account for knowing each other so well.
On his part, Gin clearly knows Shiho's personality very well as he can anticipate her movements  despite having rather different lines of work.
Gin can identify her from a single hair with sexual. As for Shiho, she hardly knew most of the other agents in non-science related positions.
She hadn't met Pisco since she was a baby, she had only heard of Chianti and Kornand hadn't heard of Kir. Conan never asked about Tequila.
Gin and Sherry
Shiho knows Vermouth despite not being in science because Detective likely had a connection with Atsushi and Elena Miyano and their research because Vermouth doesn't seem to age. Gin is on the assassination side of things, so it is anomalous how well she seems to know him given how she doesn't know much about anyone else outside of the research branch.
She has always know that Renya Karasuma is the Conan Organization head.