The high ductile-to-brittle transition temperature (DBTT) of tungsten combined with its high hardness make machining incredibly difficult. These properties typically result in the poor-quality machined surfaces and short tool life. In this study, TiAlN coated carbide tools with different rake angles (8°, 10° and 12°) were tested in conventional milling at different cutting speeds (60 m/min, 100 m/min and 150 m/min) and preheating temperatures (400°C, 500°C and 600°C). The resulting surfaces were examined, and the assessment of relevant surface/sub-surface features was performed to understand the impact of deformation. Surface examinations revealed the presence of ductile and brittle fracture regions. The study showed that machining at 60 m/min produced the best performance with the 12° rake resulting in the longest tool life while preheating has no effect. Further assessment of the tool wear at the optimized cutting speed revealed that the tool nose was the location of principal structural weakness where additional strengthening could enhance tool life.