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Fluoroquinolones are widely recommended as empirical monotherapy for community-acquired pneumonia. Since 1999, case reports of failure of levofloxacin therapy due to levofloxacin-resistant strains of Streptococcus pneumoniae have started to appear. Most worrying is that, in some cases, levofloxacin resistance has been acquired by pneumococci within days of the initiation of therapy. Because use of current clinical antimicrobial resistance breakpoints fail to identify the majority of S. pneumoniae isolates with only first-step mutations, current treatment guidelines not only may have implications with regard to the ability of surveillance programs to detect emerging resistance but may have therapeutic implications as well.