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Background: In today's competitive job market, pharmacists must have a well-crafted curriculum vitae (CV), cover letter, and personal statement. However, non-native English speakers may face challenges in crafting effective job application documents. Jordan is one such country where English is a second language for many, and little is known about the CV/job application writing skills of Jordanian pharmacists. Therefore, this study examined Jordanian pharmacists' ability to write job applications cover letters, and personal statements in English and investigated the association between several demographics and professional variables and the readability index of cover letters and personal statements., Methods: This study aimed to investigate Jordanian pharmacists' ability to write job applications cover letters, and personal statements in English and evaluate the readability of their personal statements and cover letters. The data were blindly and independently reviewed by two researchers. The readability of the cover letters and personal statements was assessed using an online calculator that assigns a readability index score. A readability score of 7-12 was considered "target", while scores above 12 or below 7 were considered "complicated" or "simple", respectively. The relationship between readability index scores and other variables was analyzed using the chi-square test with a statistical significance level of 0.05., Results: The study recruited 592 pharmacists. Most applicants, specifically 62.3%, were female, and 60.0% of them graduated more than six months before submitting their job applications. While 78.2% of the applications included a personal statement, only 34.8% included a cover letter, and 27.2% provided both. Of the 206 cover letters written in English, 43.2% were tailored, and 80.6% were structured. The study also found that the provision of an official photo was associated with providing a cover letter (P < 0.001, Phi(φ) = 0.14) while providing a structured cover letter was associated with including a personal statement (P < 0.001, Phi (φ) = 0.24). Only 102 cover letters and 65 personal statements had readability index scores within the target range., Conclusion: In this study, most Jordanian pharmacists undervalue the importance of cover letters and personal statements and lack job application writing skills. The study also highlighted the need for improved pharmacists' English proficiency to write effective job application documents in Jordan., (© 2023. The Author(s).)