Background: Organizing pneumonia (OP) accounts for ~10% of the interstitial lung diseases in patients diagnosed with rheumatoid arthritis (RA). There are only a few published studies that have described RA-associated OP (RA–OP), each with comparatively few study participants. Furthermore, despite the high frequency of secondary flareups, no studies to date have identified factors that predict RA–OP recurrence. This study aimed to clarify the clinical characteristics of RA–OP, to determine the relationship between OP and RA exacerbations, and to identify predictors of RA–OP disease recurrence.Methods: The data of 33 patients with RA–OP admitted to our hospital between 2006 and 2016 were retrospectively analysed.Results: RA onset preceded OP in 82% of patients; OP preceded or co-occurred with RA in 9% each. The median [Q1, Q3] age at first OP onset was 64.0 [55.0, 68.0] years and 5.5 [1.0, 19.3] years after RA onset. At OP onset, 42% of events exhibited unilateral shadows and 76% had normal KL-6; RA disease control remained good in 52% and was exacerbate d in only 18%. Ten (30%) patients experienced OP recurrence with an interval of 13.0 [7.5, 22.5] months between events, with a rate of first recurrence of 127 per 1,000 person-years. Compared with 14 non-recurrent cases, 10 recurrent cases showed lower age at first OP (59.5 years vs. 67.1 years; p = 0.043) and shorter period from RA to first OP (6.4 vs. 14.2 years; p = 0.047) and included more OP-preceding patients (30% vs. 0%; p = 0.029) and more ever-smokers (80% vs. 36%; p = 0.032). OP-preceding patients showed shorter median recurrence-free survival time (15 vs. 136 months; p = 0.009) and higher recurrence risk (hazard ratio, 5.5; p = 0.021). Conclusions: RA–OP showed a high recurrence rate but no association with RA exacerbation. Four predictors of RA–OP recurrence were identified.