To develop and evaluate domain-specific and pretrained bidirectional encoder representations from transformers (BERT) models in a transfer learning task on varying training dataset sizes to annotate a larger overall dataset. The authors retrospectively reviewed 69 095 anonymized adult chest radiograph reports (reports dated April 2020–March 2021). From the overall cohort, 1004 reports were randomly selected and labeled for the presence or absence of each of the following devices: endotracheal tube (ETT), enterogastric tube (NGT, or Dobhoff tube), central venous catheter (CVC), and Swan-Ganz catheter (SGC). Pretrained transformer models (BERT, PubMedBERT, DistilBERT, RoBERTa, and DeBERTa) were trained, validated, and tested on 60%, 20%, and 20%, respectively, of these reports through fivefold cross-validation. Additional training involved varying dataset sizes with 5%, 10%, 15%, 20%, and 40% of the 1004 reports.