A 43-year-old woman died suddenly and was found at PM to have a ruptured thoracic aortic aneurysm. The endothelial surface of the aorta showed a 'tree-bark' appearance. Histology of the aneurysm wall showed a patchy, mainly perivascular, plasma cell infiltrate. Multiple spirochete-like organisms were identified on T. pallidum IHC. However, PM syphilis serology (screen including rapid plasma reagin (RPR) and T. pallidum particle agglutination (TPPA)) on femoral blood was negative. PCR testing on FFPE aortic wall tissue was negative. Further history revealed routine antenatal syphilis screening tests had been negative, no known history or risk of exposure to syphilis or other treponemes. This case raises the possibility of false negative syphilis testing. While acknowledged in RPR testing, with the modern testing regime using multiple methods, the rate of false negative results is now thought to be markedly reduced, and false positive results are a much greater problem in clinical medicine. The most common cause of false negative results is early in primary infection before an immune response has been mounted and in those patients that are immunocompromised. False negative results are also more often seen in tertiary syphilis, as in this case. Newer testing methods which include 16S rRNA sequencing have become available and early discussion with a microbiologist would be recommended. Strong macroscopic and microscopic suggestion of syphilis as the cause of the aneurysm makes it necessary to include the possibility of infection in the Post Mortem Report to Coroner as this will have implications for her sexual partners and children.