, ABSTRACT Context. The evolution of the most massive stars and their upper-mass limit remain insufficiently constrained. Very massive stars are characterized by powerful winds and spectroscopically appear as hydrogen-rich Wolf–Rayet (WR) stars on the main sequence. R144 is the visually brightest WR star in the Large Magellanic Cloud. R144 was reported to be a binary, making it potentially the most massive binary observed yet. However, the orbit and properties of R144 have yet to be established. Aims. Our aim is to derive the physical, atmospheric, and orbital parameters of R144 and to interpret its evolutionary status. Methods. We performed a comprehensive spectral, photometric, orbital, and polarimetric analysis of R144. We measured radial velocities via cross-correlation. Spectral disentangling was performed using the shift-and-add technique. We used the Potsdam Wolf–Rayet code for the spectral analysis. We further present X-ray and optical WR stars ( ≈ 1 R (cid:12) ); this scenario could help resolve the observed mass discrepancy. Conclusions. R144 is one of the few very massive extragalactic binaries ever weighed without the usage of evolution models, but poses several challenges in terms of the measured masses of its components. To advance, we strongly advocate for future polarimetric, photometric, and spectroscopic monitoring of R144 and other very massive binaries.