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The cross-entropy loss decreases monotonically while the correct token never overtakes the competitor in rank. We study this regime across five transformer architectures spanning two families and a fivefold parameter range, on ten hand-selected near-synonym contexts. We instrument these failures with an order parameter combining the predicted distribution and pairwise embedding overlaps. It decomposes additively into a signal, tracking the model's commitment to the correct token over its nearest competitor, and a background drag, set by how the embedding bulk leaks probability into the score. This isolates two failure modes. In kinematic failure the signal stays small. In structural failure the drag actively worsens as fine-tuning proceeds. 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This isolates two failure modes. In kinematic failure the signal stays small. In structural failure the drag actively worsens as fine-tuning proceeds. 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