Try these in order — most captioning issues come down to one of these:

Make sure you've clicked Start transcribing (or accepted a call-detected notification) — Sidekick doesn't caption unless a session has started. If it's paused, click the pause button again to resume.

Go to System Settings → Privacy & Security and confirm both Microphone and System Audio are granted to Rylo Sidekick (unless you've chosen to type rather than speak, in which case Microphone isn't needed). See Setting up Rylo Sidekick's permissions.

Live captioning needs an internet connection. If Sidekick can't reach our captioning service, you'll see an error message in the caption window — check your Wi-Fi or network connection and try starting the session again.

If you see captions for yourself but not the other participant (or vice versa), double check both Microphone and System Audio are granted — each one covers a different side of the conversation.

Quit and reopen Sidekick, then start a new session. If the problem continues, contact us.