Anaerobic soil disinfestation (ASD) is emerging globally as an alternative to fumigant pesticides. To investigate ASD mechanisms, we monitored microbially produced volatile organic compounds (VOCs) and other volatile gases in situ using Fourier Transform Infrared Spectroscopy. Study plots infested with Fusarium oxysporum, Macrophomina phaseolina, and/or Verticillium dahliae included: organic flat ground (fASD, 6.7 + 13.5 megagrams per hectare, Mg/ha, rice bran/broccoli) and uncovered soil treated with mustard seed meal (MSM, 3.4 Mg/ha) at one site performed in fall of 2018; formed bed (bASD, 20 Mg/harice bran), control (UTC) and fumigant (FUM) at a second field site in fall of 2019 and 2021. Here, we present VOC diversity and temporal distribution. fASD generated 39 VOCs and GHGS, including known pathogen suppressors: dimethyl sulfide, dimethyl disulfide, and n-butylamine. bASD produced 17 VOCs and greenhouses gases (GHGs), 12 of which were also detected in fASD but in greater concentrations. Plant mortality and wilt score (fASD: 3.75% ± 4.79%, 2.8 ± 0.8; MSM: 6.25% ± 12.50%, 2.7 ± 0.3; bASD: 61.27% ± 11.26%, 4.1 ± 0.5; FUM: 13.89% ± 7.17%, 2.3 ± 0.2; UTC: 76.63% ± 25.11%, 4.3 ± 1.0) were significantly lower for fASD and MSM versus bASD and UTC (p < 0.05). Only FUM was not statistically different from fASD and MSM, and was significantly lower than UTC and bASD (bASD-FUM, p < 0.05; UTC-FUM, p < 0.05). The cumulative strawberry yield from bASD-treated plots was not different from FUM or UTC (bASD: 60.3 ± 13.6; FUM: 79.4 ± 9.19; UTC: 42.9 ± 12.4 Mg/ha). FUM yield was significantly greater than UTC (p = 0.005). These results, and to a far greater extent, additional challenges faced during both bASD trials, suggest that bASD is not as effective or as feasible at maintaining overall plant health as fASD or traditional fumigants. However, differences in management practices and environmental conditions at both sites across years cannot be fully excluded from consideration and many of our observations remain qualitative in nature.