Genuinely useful bug report. We hit almost this exact shape once with Amethyst's bunker — the connect handshake acked in a way our NDK version didn't recognize as success, so it silently failed even though the phone had approved it (fixed with a get_public_key fallback check). What you're describing sounds like the next request after connect (the sign_event for the image upload) — if Clave's notification isn't reliably delivered/tapped in time, the signer app never actually approves that specific request, even though connect itself worked. That's a real, known-fragile spot across NIP-46 apps generally, not specific to ditto.pub. Haven't tested Clave myself so can't confirm it's the same root cause, but worth checking if Clave has an "always allow this app" setting — that removes the per-request approval step entirely. More on how we built around this class of bug: https://app.nostras.app