Setting up "surveillance" on another character - how?

This came up in our game some time ago; I made a particular ruling on it, and on we went, but it’s turned out that, I think, I made it too easy (or at least too low of an obstacle) and that’s causing some issues down the line.

Here’s the setup - please tell me, oh gurus, how would you set up a spy ring or surveillance operation on a target to keep them under more or less constant watch, without them knowing it? And how would such a character find out about it?

For example, imagine that one character is the Chamberlain of the court. He wants to set up what I noted above on the Archcotare for his world. He’s got various skills like Observation and Security Rigging. He also has a group of “little birds” (i.e. spies) at 3D Aff (with a 2D Rep).

So, question is, how could he set up that op? Is it a matter of rolling his skills? Does he roll his group’s skills (say at 5D because he put 3 Circle Points into them)? Or is this a Circle matter (i.e., he Circles up “Super Spy” who then does the sjob based on HIS roll)? And of course, at what obstacle would this roll be set up at? And I assume it’s a building scene? Single roll, or linked test? Or what?

And, on the flip side, how would our Archcotare figure out she’s being watched, and then move to dismantle it/hide from it/cover her tracks? Is that possible? Or maybe the whole thing is some sort of versus test (whatever roll we determine above against her security detail? Or her Perception? Or what?)?

Please help! Very important to our game. It’s a thing that, depending on how wrong I was, I’ll just have them redo properly.

P.S. - Just thought of something: I think one player wanted to set up a spy satellite thing. Now that I think on it, it’s obviously tech night? So it should have been a rolled tech thing, right? Gah! Still learning…

I would:
• Use Surveillance tech (and automation).
• Make a Circles test to find a spy in his curia

Archotare better have an instinct about purging or a security officer who an Instinct about sweeping.

Hmm…yes, that makes perfect sense (especially the second one - never thought of that!).

As for the sweeping, yeah, I’ve already warned the crew that that’s happening and some rolls need to be made…

In our last game, the surveying character had an instinct to always check the day’s logs. This got him in tons of trouble.