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Background: Plantar first metatarsal ulcerations pose a difficult challenge to clinicians. Etiologies vary and include first metatarsal declination, cavus foot deformity, equinus contracture, and hallux limitus/rigidus. Our pragmatic, sequential approach to the multiple contributing etiologies of increased plantar pressure sub–first metatarsal can be addressed through minimal skin incisions. Methods: A retrospective review was performed for patients with surgically treated preulcerations or ulcerations sub–first metatarsal head. All of the patients underwent a dorsiflexory wedge osteotomy, and the need for each additional procedure was independently assessed. Equinus contracture was treated with Achilles tendon lengthening, cavovarus deformity was mitigated with Steindler stripping, and plantarflexed first ray was treated with dorsiflexory wedge osteotomy. Results: Eight patients underwent our pragmatic, sequential approach for increased plantar pressure sub–first metatarsal, four with preoperative ulcerations and four with preoperative hyperkeratotic preulcerative lesions. The preoperative ulcerations were present for an average of 25.43 weeks (range, 6.00–72.86 weeks), with an average size of 0.19 cm3 (median, 0.04 cm3). Procedure breakdown was as follows: eight first metatarsal osteotomies, four Achilles tendon lengthenings, and six Steindler strippings. Postoperatively, all eight patients returned to full ambulation, and the four ulcerations healed at an average of 24 days (range, 15–38 days). New ulceration occurred in one patient, and postoperative infection occurred in one patient. There were no ulceration recurrences, dehiscence of surgical sites, or minor or major amputations. Conclusions: The outcomes in patients surgically treated for increased plantar first metatarsal head pressure were evaluated. This case series demonstrates that our pragmatic, sequential approach yields positive results. In diabetic or high-risk patients, it is our treatment algorithm of choice for increased plantar first metatarsal pressure.