We report on the first X-ray absorption fine structure (XAFS) and near edge X-ray absorption fine structure (NEXAFS) spectroscopy are well established methods for retrieving structural information about the composition of solid state materials and soft matter. The water window spectral range between 284 eV and 543 eV is of special interest as it contains the K-shell absorption edges of the biological building blocks: carbon (284 eV), nitrogen (410 eV) and oxygen (543 eV). Up until recently only facility scale light sources have been capable of generating coherent water window radiation: synchrotrons with a high degree of spatial coherence and hundreds of femtoseconds pulse durations, and X-ray free electron lasers with a high degree of spatial coherence and femtosecond temporal resolution [1]. High harmonic generation (HHG) [2, 3] offers an attractive alternative approach since it is realizable on a small table-top scale and is capable of generating fully coherent radiation, i.e. femto-to atto-second and possibly even zeptosecond pulse durations. The ability to generate coherent water window radiation from HHG is extremely exciting as it would bring ultra-short time resolution to structural probing with a table top method. HHG is most commonly driven by Ti:sapphire sources at 800 nm with the highest achievable photon energy, the so called cutoff, scaling linearly with the laser intensity and quadratically with the driving wavelength [4]. While the water window range is reachable with such sources via nonphase-matched HHG [5], the contradicting requirements of increasing the cutoff with higher laser intensity while avoiding excessive ionisation, severely limits the achievable flux in the water window. A solution to this dilemma is to use a source with a similar peak intensity and pulse duration, but at much longer emission wavelengths in order to exploit the quadratic wavelength scaling of the HHG cutoff. A drawback of such an approach is the unfavourable single atom response scaling of harmonic yield with λ −9 [6] which can however be mitigated, to a large extent, through high gaspressure phase matching [7]. This concept was demonstrated by reaching a 1.6 keV cutoff when driving with a mid-IR laser system [8]. Despite this cutting-edge result, the 20 Hz repetition rate and stability of the system have thus far proved insufficient for applications, thereby underlining the need for significant improvements of the laser parameters.We find that while high X-ray flux can be achieved through phase-matched HHG driven by kHz or higher repetition rate long-wavelength sources, achieving sufficient intensity and carrier to envelope phase (CEP) stability of the driver laser is an essential key both for producing attosecond pulses and for generating reproducible X-ray spectra from each laser pulse and throughhout an X-ray measurement.Currently at the kHz level and with long wavelength drivers, the lower end of the water window at 300 eV was reached using a Ti:sapphire pumped optical parametric amplifier (OPA) at 1.5 μm [9]...