Background <p>First permanent molars (FPMs) in children are frequently affected by extensive caries or molar–incisor hypomineralization, making their long-term restoration challenging. Stainless steel crowns (SSCs) have been the traditional full-coverage treatment for compromised FPMs, whereas CAD/CAM-based indirect restorations (IDRs) offer a more conservative, tooth-colored alternative. However, evidence comparing the real-world clinical performance and esthetic satisfaction of SSCs and IDRs in pediatric patients is limited.</p> Methods <p>This retrospective, exposure-based cohort study included children aged 7–14 years treated in a university-based pediatric dentistry clinic who received either an SSC or a CAD/CAM-based IDR on at least one FPM and had a minimum clinical follow-up of 12 months. Restoration type was determined by routine clinical decision-making (extent of structural compromise, pulpal status, occlusion, patient cooperation, and parental esthetic preferences), not by randomization. The SSC comparison sample was selected from an eligible/reachable source pool with the aim of balancing sex and age category at the patient level; this was not a formal pair-matched design. Clinical performance was evaluated using modified United States Public Health Service (USPHS) criteria. Esthetic satisfaction was assessed using separate 10-point visual analogue scales for children and parents. Statistical analyses were exploratory and included generalized estimating equations (GEE) to account for clustering of multiple restorations within patients, chi-square/Fisher’s exact tests, and Mann-Whitney U tests, as appropriate.</p> Results <p>Sixty children (30 boys, 30 girls; mean age 11.3 years, range 7–14 years) with 78 restored FPMs were included: 39 SSCs and 39 IDRs. The mean follow-up period was 14.2 ± 2.7 months. According to modified USPHS criteria, most parameters showed no statistically significant between-group differences (<i>p</i> &gt; 0.05); however, marginal adaptation and gingival health differed between groups (both <i>p</i> = 0.01). One SSC and one IDR received a Charlie score for secondary caries or retention. Among IDRs, both resin nano-ceramic (<i>n</i> = 25) and lithium disilicate (<i>n</i> = 13) restorations showed favorable short-term outcomes; given the small subgroup sizes and design heterogeneity, material-specific comparisons were descriptive. Children reported high esthetic satisfaction with both SSCs and IDRs (mean scores 9.2 ± 1.4 and 9.9 ± 0.4, respectively; <i>p</i> = 0.008). Parents showed higher esthetic satisfaction with IDRs compared with SSCs (10.0 ± 0.2 vs. 8.8 ± 2.1; <i>p</i> = 0.003), although absolute scores for SSCs remained high.</p> Conclusions <p>In this retrospective cohort, selected compromised first permanent molars restored with either SSCs or CAD/CAM-based IDRs showed favorable short-term outcomes after a minimum 12-month follow-up. IDRs were associated with higher esthetic satisfaction, particularly among parents. Given the non-randomized treatment allocation, baseline differences between groups, and heterogeneity within the IDR group, these findings should be interpreted as observational and hypothesis-generating rather than evidence of comparative effectiveness. Longer-term prospective studies with standardized baseline characterization are warranted.</p>