Enterococcus species inhabit the human gastrointestinal tract and may be recovered from urine, wounds, abdominal specimens, and blood. Their isolation raises a recurring clinical question: does the organism represent harmless colonization, contamination, or a causative pathogen requiring treatment? This narrative review synthesizes contemporary clinical guidelines and selected studies, emphasizing practical interpretation across specimen types, species-level identification, and antimicrobial stewardship. Enterococcus faecalis and Enterococcus faecium differ substantially in epidemiology, antimicrobial susceptibility, and association with healthcare exposure. Asymptomatic bacteriuria generally should not be treated, except during pregnancy or before selected endourological procedures associated with mucosal trauma. Conversely, enterococcal bloodstream infection requires prompt clinical assessment, source investigation, and consideration of endocarditis, especially for E. faecalis. Deep or normally sterile-site specimens provide stronger evidence of pathogenicity than superficial swabs or surveillance cultures, although specimen quality and the possibility of contamination remain critical. Intra-abdominal isolation must be interpreted in relation to source control, severity, healthcare association, and polymicrobial growth. Species identification, susceptibility testing, and targeted therapy are essential because intrinsic cephalosporin resistance and acquired vancomycin resistance limit treatment options. A stepwise clinical–microbiological framework can reduce both missed invasive infections and unnecessary antibiotic exposure. Enterococci should neither be dismissed reflexively nor treated solely because a culture is positive; management must be driven by syndrome, specimen validity, host factors, and the strength of microbiological evidence.