With cloak of pain you should be able to stay in stealth because it triggers infiltrate a second time. But if you are using dual weapons the one attack often counts as 2 ( for example dagger heavy attacks) because both weapons hit the target at once.
This explains the wonky behaviour I was having recently when I came back to finish my Shade challenges for Chaos Wastes. I still don’t understand how FS manages to break some many things with each larger update. It’s like the devs have no idea how to properly use version control on sourcetree/gitlab or whatever service they’re using to manage their dev branches. It’s not even funny anymore. Especially after the tidal wave of reintroduced bugs when Winds of Magic released.