Purpose: To compare clinical and esthetic outcomes between immediately loaded single implants placed with and without a fully guided surgical procedure. Materials and Methods: Patients with a missing maxillary tooth (second premolar to second premolar) were considered for inclusion in this 1-year prospective nonrandomized study. Exclusion criteria were general health contraindications for oral surgery besides the need for bone grafting or ridge augmentation. One group received digital implant planning, fully guided surgery, and immediate loading (DIL). The other group received freehand surgery and immediate loading (IL). Outcome measures were implant survival, marginal bone loss, soft tissue changes, papilla index, pink and white esthetic scores (PES and WES, respectively), and patient-reported outcome measures (PROMs). Results: Two of 21 implants failed in the DIL group soon after placement, resulting in a 1-year implant survival rate of 90.5%, while no implants failed in the IL group. Significantly higher papilla index scores and lower soft tissue changes were found for the DIL group compared to the IL group. No differences were found after 1 year regarding marginal bone loss, PES, WES, or PROMs. Conclusion: Within the limitations of this study, immediate loading in combination with fully guided surgery might negatively affect implant survival. Immediate loading, fully guided surgery, and a digital workflow appear to have a positive effect on early soft tissue adaptation.