Background/Objectives: This study aimed to evaluate whether liver stiffness (LS), as assessed by transient elastography (TE), is increased in patients with systemic sclerosis (SSc) and to identify the factors associated with LS. Methods: In this exploratory cross-sectional study, the LS value and the prevalence of LS ≥ 5.3 and LS ≥ 7.5 kPa in 94 SSc patients and 50 healthy controls (HCs) were compared by univariate and multivariate analyses (adjusted for age and sex). TE was performed using FibroScan^® and LS values were expressed in kPa. Clinical and laboratory variables were analysed as factors potentially associated with LS, LS ≥ 5.3 kPa and LS ≥ 7.5 kPa, in exploratory analyses adjusted for a pre-specified set of confounders. Results: Among the 94 SSc patients, 79 (84%) were female; median age was 59 (49–70) years, and median disease duration was 8 (3–13) years. LS was significantly higher in SSc patients than in HCs in both univariate (5.12 ± 1.95 vs. 4.18 ± 0.98 kPa, p < 0.001) and multivariate analyses (β = 0.289, p = 0.001), with a higher prevalence of LS ≥ 5.3 kPa (40.4% vs. 10.0%, adjOR 6.85, p = 0.001) and LS ≥ 7.5 kPa (11.7% vs. 0%, p = 0.009). Only a limited number of factors were associated with LS abnormalities: telangiectasias (β = 0.222, p = 0.044) and glutamic–oxaloacetic transaminase (GOT) (β = 0.278, p = 0.012) for LS, and GOT (adjOR 1.082, p = 0.020) and anti-centromere antibodies (adjOR 4.09, p = 0.017) for LS ≥ 5.3 kPa. In univariate analysis, LS ≥ 7.5 kPa was associated with pulmonary hypertension (p = 0.049), pre-capillary pulmonary hypertension (p = 0.011), and GOT (p = 0.032); no multivariate model was fitted because of the few events. Conclusions: SSc patients show increased LS values and a higher prevalence of both LS ≥ 5.3 kPa and LS ≥ 7.5 kPa than HCs, easily detectable by TE. These findings are exploratory and require confirmation in larger cohorts to determine whether increased LS in SSc reflects hepatic fibrosis and whether it carries clinical and prognostic implications.