Using the boronate ester probe P1 shown in Scheme 1B, detection of submicromolar or subnanomolar concentrations of H2O2 or a naphthoquinone, respectively, within 1 hr was demonstrated. Although these analytical performances are significantly better than those previously achieved for H2O2 by DCR, they are still limited by the lack of chemical stability of P1, which in the absence of the trigger tends to slowly self-deprotect into a naphthohydroquinone. This lack of stability turns out to be intrinsic to the self-immolating spacer installed on the probe, a recurrent issue of molecular probes based on self-immolation and which is at the origin of the unsatisfactory analytical performances encountered so far. To access more robust and stable probes, it is thus important to design probes that no longer rely on self-immolation. This is what we address here with the new boronate-based probes shown in Scheme 1C. Instead of introducing the masking boronate ester function via a remote self-immolating spacer, we have chosen to place it directly on the naphthyl ring, leading to either the single-protected naphthol monoboronate ester probe P2 or the doubly protected naphthyl diboronate ester probes P3 and P4. By reaction with H2O2, these probes are expected to release a 1,4-naphthohydroquinone (1,4-NQH2), which in the presence of O2 spontaneously autoxidizes into 1,4-naphthoquinone (1,4-NQ) with concomitant regeneration of H2O2, as previously shown with P1. Another important feature we have considered here is to design boronate probes with an improved reactivity towards H2O2 as well as an optimized redox cycling capability, with the underlying idea to outcompete the background reactions. As it will be shown, the single-protected probe P2 generates a remarkably efficient autocatalytic reaction (LOD of 0.1 µM H2O2 in less than 10 min at pH 8.5) thanks to a fast H2O2-mediated deprotection rate (kd) (faster than P1). However, the lack of chemical stability of P2 pushed us to opt for a double masking strategy, as exemplified with probes P3 and P4, which finally enable us to obtain much more stable boronate probes while keeping a good reactivity towards H2O2. With these doubly protected probes, detection of nanomolar concentrations of H2O2 in less than 10 min was achieved using a simple UV-visible absorbance readout, which in terms of analytical performance is competitive with the best fluorescent-based molecular probes currently available on the market for quantitative analysis of H2O2 by fluorescence. Finally, we will show that these excellent analytical performances could be obtained thanks to a comprehensive kinetic analysis of the complex cross-catalytic reaction network, thus providing an access to its quantitative prediction and rationalization. In particular, we were able to explain why the autocatalysis is still possible for doubly protected probes even in the absence of instability of the monoprotected intermediate.