Objective: To identify clinical, serological, and pharmacological factors associated with dry eye disease (DED) in patients with rheumatoid arthritis (RA). Methods: In a retrospective cohort, 65 adults with RA (2010 American College of Rheumatology / European League Against Rheumatism criteria) underwent a TFOS DEWS II-based ocular surface workup, with 65 age- and sex-matched non-RA clinic participants for descriptive comparison. Group comparisons used t-test, Mann–Whitney U-test, χ2, or Fisher’s exact tests. A multivariable logistic regression model with anti-CCP positivity, smoking, anti-SSA, and age was fitted; discrimination was assessed by ROC analysis, and calibration by the Hosmer–Lemeshow test. Results: Dry eye disease was present in 19 of 65 RA patients (29.2%); for descriptive context, prevalence in 65 matched non-RA ophthalmology clinic participants was similar (27.7%; P = .85). Anti-CCP positivity (89.5% vs. 60.9%; P = .037) and cumulative pack-years (median 10.0 vs. 0.0; P = .032) separated RA-DED from RA without DED, whereas disease activity, glucocorticoid dose, methotrexate, and hydroxychloroquine exposure did not. Given only 19 events, the model was fitted with Firth penalized likelihood; anti-CCP positivity remained independently associated with DED (adjusted odds ratio (aOR) 4.20; 95% CI, 1.10-23.77; P = .035), and smoking showed a directionally consistent effect (aOR 2.42; 95% CI, 0.81-7.64). Model discrimination was moderate (AUC 0.757) with adequate calibration. Conclusion: Within this RA cohort, anti-CCP positivity was independently associated with DED, whereas cumulative tobacco exposure showed a directionally consistent association that did not reach independent significance. These findings support consideration of targeted ocular surface surveillance in anti-CCP–positive patients with a smoking history, pending confirmation in larger prospective studies.