Several methods for extracting the chlorophyll sensitive red-edge position (REP) from hyperspectral data are reported in literature. This study is a continuation of a recent paper published as 'A new technique for extracting the red edge position from hyperspectral data: the linear extrapolation method'. The method was validated experimentally for estimation of foliar nitrogen concentrations of rye, maize and mixed grass/herb. The objective of this study was to test the utility of the linear extrapolation method under different conditions including variable canopy biophysical parameters, solar zenith angle, sensor noise and spectral bandwidth. REPs were extracted from synthetic canopy spectra that were simulated using properties optique spectrales des feuilles (PROSPECT) and scattering by arbitrarily inclined leaves (SAILH) radiative transfer models. REPs extracted by the linear extrapolation method involving wavebands at 680, 694, 724 and 760 nm produced the highest correlation (R2=0.75) with leaf chlorophyll content with minimal effects of leaf and canopy biophysical confounders (leaf area index, leaf inclination distribution and leaf dry matter content) compared to traditional techniques including the linear interpolation, inverted Gaussian modelling and polynomial fitting techniques. In addition, the new technique is insensitive to changes in solar zenith angle. However, the advantage of using the linear extrapolation method compared to the various alternative methods diminishes with increasing sensor noise and decreasing spectral resolution. In summary, the linear extrapolation technique confirms its high potential for leaf chlorophyll estimation. The efficacy of the technique under field conditions needs to be established.