Recent evidence suggests that the use of suture button devices for ankle syndesmosis fixation is increasing. Multiple studies have shown some concern about damaging the greater saphenous neurovasculature with placement of the anchor point on the medial tibial cortex. We hypothesized that an all-inside button deployment technique would allow for a low risk to medial soft tissue structures. A total of 40 syndesmosis suture buttons were placed into 10 separate cadaveric lower limbs, using the newly developed technique. Four suture buttons were sequentially placed from distal to proximal in each limb within the zone of typical syndesmosis fixation, using fluoroscopic guidance. A medial incision was then performed to evaluate the relationship of the suture buttons to the medial soft tissue structures and the medial malleolus. Thirteen of 40 suture buttons (32.5%) were placed anterior, 7 (17.5%) posterior, and 20 (50%) with a portion of the button directly deep to the saphenous vein. Two of 40 buttons (5%) were placed within the tibial periosteum, and 38 (95%) were subfascial and directly superficial to the periosteum. Four of 40 (10%) limbs revealed a perforation in the saphenous vein from the guidepin. In conclusion, risks to the medial neurovascular structures exist with the medial deployment technique, but they appear to be mitigated compared with previous publications. The necessity of a medial incision to evaluate for soft tissue entrapment may not be necessary in all patients, as this technique appears to be safe, accurate, and reproducible.