Medication error is an inappropriate medication use that may lead to patient harm if not prevented. Thus, providing patient medication counseling by the community pharmacists can reduce this problem. This study used correlational survey design aimed to determine the influence of the extent of challenges such as system, pharmacy environment, patient and pharmacist encountered by community pharmacists on patient medication counseling. Purposive sampling method was used with 35 respondents working in drugstores within downtown area in Davao City. Results were statistically treated with frequency and percentage for the demographic profile, one-way anova and t-test and pearson r product-moment correlation for the level of capability on counseling and the extent of challenges encountered by the respondents. Based on the treatment, it showed that majority of the respondents were female 21-30 years old, female, single and served between 1-5 years in chain pharmacy. Generally, they are moderately affected by the system, patient and pharmacist challenges but highly challenged in the aspect of pharmacy environment. The level of capability in terms of knowledge and attitude revealed moderate result but demonstrated high in the practices. Also, there was no significant difference in the capability of the respondents on counseling when analyzed according to demographic profile and no significant difference between the extent of challenges encountered and their level of capability.