Tahoe repeatedly asking to "bypass the window picker"

[Larsenv]

Every time I restart my computer or even randomly while using it, I keep getting prompts to have CleanShot + Barbee bypass the window picker repeatedly. I’ve tried adding and removing the apps from the privacy panel, including granting them full disk access, and editing the plist file to prevent them from expiring.

I’m using a Mac Mini M4 with 256GB of storage and running macOS 26.2, so I have my user directory on an external SSD.

Could you please help me understand why this is happening? Is it related to my external SSD? It’s very annoying.

 

[Starfia]

I know macOS has moved to specialized developer APIs in recent years that essentially allow access to user-facing video and audio content on a per-screen and per-window basis before they reach the lower-level framebuffer, partly for efficiency and partly for user privacy reasons: when apps participate, the user can choose what they're sharing with apps on those bases. Subsequent to offering these new APIs and deprecating the old ones, macOS also ramped up its alerts about apps still using them. (MacRumors previously covered this topic here and here.)

I'm not sure whether the frequency you're seeing has to do with the external location of your home directory, but I think it's right to consider it.