Tree stabilization systems are specified by landscape architects to promote stability and maintain posture at transplant. However, staking and guying can compromise tree health. I investigated the effects of such stabilization systems on tree health to inform landscape architectural planting specifications. Through field investigations, trees were assessed for their health and the use of a stabilization system. Ten health symptoms were recorded for 488 trees in Guelph, Ontario. Results showed symptoms of stunted growth, death and pest/disease were fewer on trees observed with a TSS. Health was negatively impacted by TSS by producing more symptoms of a girdled trunk, swelling and wilting. Trees planted on public land were found to benefit from being stabilized while trees on private land expressed negative health effects when observed with trunk support. Implications for landscape architects include limiting tree stabilization practice to site conditions where their use is warranted along with timely removal.