One thing is for sure Kuroda knows Rumi.
SO there are two ways to Rumi-Kuroda story.
I will try to keep my points related to 987 only.
1. Rumi is Kuroda's apprentice/collegue
So the first point says the whole story itself, And I even gave my view on this previously on any other thread, that i don't remember.
Anyway, So Rumi had been undercover all this time, Note the fact that Rumi came after Kuroda was introduced, So the possibility is Kuroda gained his position and then, After getting all the things needed he called Rumi, made her go undercover and after he noticed conan, he found the perfect plan and established her as a teacher.
2. Rumi is on the Run from Kuroda/Rumi is BO/ Rumi is the uploader for the Kohji Haneda's case
When Kuroda heard the reference related to Rumi he was shocked. Not only that he was giving the looks of a hunter(I think).
Not to forget that he was searching for the Haneda case himself in the start.
Now more instances from the file.
1. Kuroda viewing website having kohji haneda's case, to gain more on the case on which he worked and to probably get to know its status (Maybe)
2. Given the fact that he starts to think about Rumi simultaneously while thinking of the case make me wonder how and why? He got this link between both of them.
3. Intriguing thing i found in this chapter was Shiratori's way of speaking, He was telling Kuroda about Agasa and Conan as if Kuroda knows everything about them and meets them every now and then.(Probably I am thinking way too much)
4.The part when Kuroda states the phrase " Unlike her/ That's not liker her " , gives a different aspect of their relationship as to how and why kuroda is so devious (for the time being).
5.Conan going through previous encounters with Rumi and also giving a flashback to her part of work, she did to claim conan's help. The doorway to basement all cleaned, the receipt to all the stuff she bought that day etc, making him come to a final conclusion that rumi wants conan in what way he doesn't know though.
6.Last but not least the glare-stare between Rumi and kuroda was something Rumi never expected nor wanted.
7. Not to forget when he said Kogoro's Bag of Wisdom, I think he knows the truth about Sleeping Kogoro. Who knows he may even know who shinichi is ..