Introduction: Illegible handwritten prescriptions for look-alike sound-alike medications (LASAMs) compromise pharmaceutical service quality, dispensing errors, and patient safety risks. Methods: To date, little is documented on the real dispensing practices of Libyan community pharmacists when presented with illegible prescription orders involving poorly handwritten LASAMs. Therefore; this cross-sectional study using simulated patient methodology, was performed to assess predictors for dispensing errors among 400 community pharmacists and evaluate their ability to interpret and dispense illegible handwritten prescriptions of LASAMs. Four prescriptions, each with 1–4 items (10 total items, including either Duphalac® or Duphaston®) were evaluated, yielding a thousand measurements. Results: The findings revealed significant challenges in interpreting illegible handwritten prescriptions, with 45.5% of pharmacists correctly identifying the LASAM. Generic drug names as Aspirin (94%) and Dexamethasone (77%), were interpreted more accurately compared to brand names like Utrogestan® (21%) and Pregnyl® (12%). Key predictors of dispensing errors include: single drug item prescriptions ([AOR] [95% CI]: 1.842 [1.15-2.950]; p = 0.011), crowded pharmacy ([AOR] [95% CI]: 2.165[1.256- 3.731]; p = 0.005), and evening visits ([AOR] [95% CI]: 1.983[1.119- 3.517]; p = 0.019). Pharmacists who sought additional information ([AOR] [95% CI]: 0.330 [0.208- 0.524]; p < 0.001), or referred patients to the physician ([AOR] [95% CI]: 0.241 [0.124- 0.468]; p < 0.001) achieved correct dispensing, reducing errors by 67% and 75.9%; respectively. Conclusion: Urgent systemic interventions, including the implementation of Computerized Physician Order Entry (CPOE) systems, standardized prescription-writing practices, and targeted pharmacists training programs are critical to enhance patient safety in Libya’s healthcare system.