Insomnia is one of the most common minor ailments to which patients seek advice in a community pharmacy setting. Due to the availability of a wide variety of over-the-counter (OTC) products, community pharmacists are in the front line to safe-guard patients looking for self-medication or advice for treatment of insomnia. The purpose of this study was to assess the content of community pharmacists' interactions with patients seeking advice for insomnia in Jordan. A cross-sectional study using a simulated patient methodology was conducted across a stratified convenience sample of community pharmacies in three major cities in Jordan. The visits were evaluated using pre-defined criteria adapted from published literature relating to content and counseling skills. Visits were audio-recorded using a hidden microphone and the simulated patient completed a data collection form immediately after each visit. A total of 67 community pharmacies (response rate = 93.0%) agreed to participate and were all visited once by the simulated patient. The median duration of the visit was 2 minutes (range: 0.2-4 minutes). The majority (86.6%) of visits resulted in the sale of a drug, most commonly a combination product (paracetamol and diphenhydramine) for 30 recommendations (44.8%). This was followed by a natural plant extract combination product, namely valerian and lemon balm (Melissa officinalis L.) for 23 (34.3%). Pharmacists often did not question medical history or other symptoms prior to product sale. Frequently, the recommended dose (49.3%) and administration time (38.8%) were the only information provided to the patient. No information was provided in relation to potential drug interactions or contraindications. No advice was offered on lifestyle or good sleeping hygiene. This study provided evidence that community pharmacists in Jordan in general did not offer adequate counseling for patients seeking advice for insomnia. Exploration of the reasons and factors contributing to this practice and highlighting professional opportunity and responsibility is recommended.