The current study evaluated 17 loads of cull beef cows transported in Canadian winter conditions to assess in-transit temperature and humidity, evaluation of events during loading and unloading, and animal condition and bruising. Regardless of the use of boards to block ventilation holes in trailers, temperatures were higher within trailers than at ambient locations during both travel and stationary periods (P < 0.01). Boarding was associated with smaller differences in trailer temperature, compared with ambient conditions, while the trailer was traveling at highway speeds versus when trailers were stationary (P < 0.01). Moisture levels within trailers were not different from ambient conditions when loads using boarding were traveling (P < 0.01), whereas loads without boarding had a larger difference (P < 0.01). The moisture within trailers relative to ambient conditions increased when trailers were stationary compared with traveling when boarding was used (P < 0.01). The majority of cattle transported were in good body condition (97.4% within BCS of 2 to 3.5) and had calm temperaments (96.7%). Although all comparisons were made, only the doghouse compartment had an increased risk of severe bruising compared with all other compartments (odds ratio [95% confidence interval]: 3.0 [1.6–5.5], 3.7 [2.1–6.4], 2.2 [1.3–3.7] and 3.8 [1.5–9.6] in comparison with the back, belly, deck, and nose compartments, respectively; P < 0.05). Increasing the duration of waiting to unload 30 min relative to a 1 h duration increased the odds of severe bruising by 1.18 times (95% confidence interval: 1.09–1.29; P < 0.01). Scoring systems that have been developed for auditing unloading of cattle had limited variation across loads at both loading and unloading. Pretransport assessment of animal condition using the American Meat Institute's compromised animal score was the only scoring system that was consistent with posttransport scores. We inferred from the temperature and humidity data in the current study that under commercial conditions, boarding may increase ventilation within trailers during travel and decrease ventilation during stationary periods. The current study provides the first indication that issues in Canadian cull cow transport may be related to pretransport animal condition and management of unloading.