Background In the presence of pain over the lateral aspect of the foot or recurrent ankle sprain in children, medical imaging is often employed to investigate potential causes, such as a calcaneonavicular coalition or a too-long anterior process (TLAP) of the calcaneus. Diagnosis and categorization of calcaneonavicular coalitions (synostosis, synchondrosis, or synfibrosis) is generally facilitated through imaging, in contrast to TLAP, which lacks well-defined semiological characteristics, apart from a calcaneonavicular space measurement of less than 5 mm. However, this measurement initially performed on an oblique view radiograph can be subject to a lack of precision due to positional variations of the foot and overlapping bones. Furthermore, the differentiation between TLAP as an anatomical variant and TLAP syndrome (characterized by symptomatic presentation), remains a subject of uncertainty. Objective The objective of our retrospective study was to investigate the imaging diagnosis of TLAP syndrome. Materials and methods A retrospective unmatched case-control study was conducted, covering data from February 2014 to January 2021. All patients, included retrospectively and consecutively, were initially managed in our hospital with radiography and/or computed tomography (CT) and/or magnetic resonance imaging (MRI). Two radiologists independently reviewed the images taken (radiographs, CT scans, and MRIs) of patients undergoing treatment in pediatric orthopedics for TLAP syndrome and control subjects, utilizing a standardized questionnaire. The control group consisted of subjects with no features suggestive of TLAP syndrome. The questionnaire included measurements of the calcaneonavicular space and identification of indirect signs associated with calcaneonavicular coalitions, as described in the related literature. Results A total of 128 patients who met the inclusion criteria were included in the analysis, including 38 patients and 90 controls. The prevalence of TLAP was 71.5% in the study population and 62.6% among controls. A threshold measurement of the calcaneonavicular space at 3.2 mm favored TLAP syndrome (sensitivity=97%, specificity=70%, area under the curve [95% confidence interval] =0.881[0.812–0.949]), with better precision using CT. Three indirect signs were significant: the “anteater nose” sign, the talar beak, and the tapered anterior calcaneal process. These signs demonstrated an even stronger association with TLAP syndrome when observed in conjunction with a reduction in the calcaneonavicular space, particularly in CT scans. Conclusion TLAP is common among control subjects. Therefore, a variant appears to be the most plausible explanation and it can be considered a mild form of calcaneonavicular coalition. However, in conjunction with symptoms suggestive of TLAP syndrome, the diagnosis is further supported by imaging, specifically with a calcaneonavicular space measurement of less than 3.2 mm. This measurement is most accurately obtained using CT with 2-dimensional reconstructions in all three planes. The simultaneous presence of the “anteater nose” sign, the talar beak, or the tapered anterior calcaneal process provides additional diagnostic evidence. In the diagnostic approach of calcaneonavicular coalition, oblique foot radiography seems useful in initially detecting abnormal coalition (bony or not), and complementarily, CT emerges as the best modality to characterize TLAP syndrome.