Background: Athletes training in heat experience physiological and perceptual symptoms that risk their safety and performance without adaptation. Purpose: We examined the changes in environmental symptoms, assessed with the Environmental Symptoms Questionnaire (ESQ), during heat acclimatization (HAz), heat acclimation (HA), and intermittent heat training (HT). Methods: Twenty-seven participants (mean ± standard deviation [M ± SD], age of 35 ± 12 y, VO2max of 57.7 ± 6.8 mL·kg−1·min−1) completed five trials involving 60 mins of running (60% vVO2max) followed by a 4 km time trial in heat (M ± SD, temperature of 35.5 ± 0.7 °C, humidity of 46.4 ± 1.5%). The trials occurred at baseline, post-HAz, post-HA, at week 4 of HT (post-HT4), and at week 8 of HT (post-HT8). The participants completed HT once/week (HTMIN), completed HT twice/week (HTMAX), or did not complete HT (HTCON). ESQ symptoms, thermal sensation (TS), and heart rate (HR) were measured pre- and post-trial. Results: Post-ESQ symptoms improved post-HA (3[0.40, 4.72], p = 0.02) and post-HAz (3[0.35, 5.05], p = 0.03) from baseline. During HT, symptoms improved in the HTMAX group and worsened in the HTMIN and HTCON groups. Symptoms improved in the HTMAX group versus the HTCON group at post-HT8 (4[1.02, 7.23], p = 0.012). Higher TS and HR values were weakly associated with ESQ symptoms during HT (r = 0.20, p = 0.04), only explaining 20% of variance. Conclusions: ESQ symptoms improved during HAz, HA, and HT 2x/week. ESQ symptoms were not statistically correlated with HR during exercise heat stress. TS was not sensitive to detecting adaptation and did not subjectively change. The ESQ may be valuable in monitoring adaptation and may contribute to performance post-acclimation.