Aims The aim of this retrospective study was to evaluate the rate of conversion to surgical release after a steroid injection in patients with a trigger finger, and to analyze which patient- and trigger finger-related factors affect the outcome of an injection. Methods The medical records of 500 patients (754 fingers) treated for one or more trigger fingers with a steroid injection or with surgical release, between 1 January 2016 and 1 April 2020 with a follow-up of 12 months, were analyzed. Conversion to surgical release was recorded as an unsuccessful treatment after an injection. The effect of patient- and trigger finger-related characteristics on the outcome of an injection was assessed using stepwise manual backward multivariate logistic regression analysis. Results Treatment with an injection was unsuccessful in 230 fingers (37.9%). Female sex (odds ratio (OR) 1.87 (95% confidence interval (CI) 1.21 to 2.88)), Quinnell stage IV (OR 16.01 (95% CI 1.66 to 154.0)), heavy physical work (OR 1.60 (95% CI 0.96 to 2.67)), a third steroid injection (OR 2.02 (95% CI 1.06 to 3.88)), and having carpal tunnel syndrome (OR 1.59 (95% CI 0.98 to 2.59)) were associated with a higher risk of conversion to surgical release. In contrast, an older age (OR 0.98 (95% CI 0.96 to 0.99)), smoking (OR 0.39 (95% CI 0.24 to 0.64)), and polypharmacy (OR 0.39, CI 0.12 to 1.12) were associated with a lower risk of conversion. The regression model predicted 15.6% of the variance found for the outcome of the injection treatment (R2 > 0.25). Conclusion Factors associated with a worse outcome following a steroid injection were identified and should be considered when choosing the treatment of a trigger finger. In women with a trigger finger, the choice of treatment should take into account whether there are also one or more patient- or trigger-related factors that increase the risk of conversion to surgery. Cite this article: Bone Joint J 2022;104-B(10):1142–1147.