By combatting erosion and increasing habitat, mangrove living shorelines are an effective alternative to hard-armoring in tropical and subtropical areas. An experimental red mangrove living shoreline was deployed within Mosquito Lagoon, Florida, using a factorial design to test the impact of mangrove age, breakwater presence, and mangrove placement on mangrove survival within the first year of deployment. Mixed mangrove age treatments were included to identify if seedling (11-month-old) survival could be enhanced by the presence of transitional (23-month-old) and adult (35 to 47-month-old) mangroves. Environmental factors were monitored to detect possible causes of mangrove mortalities. Approximately half (50.6%) of mangroves died, and of those, 90.7% occurred within the annual high-water season, and 88.9% showed signs of flooding stress. Planting seedlings haphazardly among older mangroves did not attenuate enough wave energy to significantly increase seedling survival. Breakwaters alleviated stress through a reduction in water velocity and wave height, increasing the odds of survival by 197% and 437% when mangroves were planted in the landward and seaward rows, respectively. Compared to seedlings, deployment of adult mangroves increased survival odds by 1087%. Collectively, our results indicate that sites with a high-water season should utilize a breakwater structure and mangroves with a woody stem.