Introduction. Uncontrolled deformity, deep infection, and/or ischemia-hypoxia are highly associated with healing challenges of diabetic foot ulcers (DFUs). This paper reports the occurrences of these factors that the authors label the “Troublesome Triad” (TT) in a prospective series of 62 patients with diabetes mellitus (DM), who were hospitalized because of their DFUs. Materials and Methods. With Institutional Review Board approval, the authors gathered data in a prospective series of patients hospitalized because of lower extremity wounds. From this data, they analyzed the DFU cohort for the incidence of each of the components of the TT. The severity of the wound was graded with the authors’ 0 to 10 Wound Score in the patients who had components of the TT and compared with those who did not. Results. One or more components of the TT were observed in 57 patients (91.9%). As the number of confounders increased, mean Wound Scores decreased from 5.2 for 1 confounder to 2.9 for 3 confounders (P = 0.003). Most patients had 1 or 2 confounders (38.7% and 45.2%, respectively), while only 5 (8.1%) patients had all 3 confounders. Unresolved infection was the major confounder in 38 (61.3%) patients, uncontrolled deformity in 31 (50.0%), and ischemia-hypoxia in 26 (41.9%). Conclusion. For those patients with DM who were hospitalized because of DFUs, confounders that require remedial interventions were present in more than 90% of patients. Recognition and management of the TT eliminates wasteful uses of resources in an attempt to heal lower extremity wounds in patients with DM where the confounders need to be addressed first.