A common intuition is that sentence embeddings should adapt to the difficulty of the input. We test this intuition in a controlled, multi-seed setting: a lightweight post-encoder adapter attaches to a frozen Qwen3-Embedding-0.6B encoder, accessing only its final pooled embedding, and is evaluated on four paraphrase and semantic-similarity tasks (PAWS, MRPC, QQP, STS-B). The naive form of the idea fails: surface-based per-sentence complexity is nearly uncorrelated with frozen-baseline error (Pearson approximately 0.05) and provides no advantage over constant or shuffled controls, while degrading a saturated baseline. Even when the target is aligned to a non-circular pair-difficulty signal, the per-sentence gate still cannot reliably capture difficulty because difficulty is primarily a property of the pair, not the individual sentence. In contrast, a small pair-level residual gated by a held-out cross-encoder difficulty signal yields consistent gains on the larger and graded tasks, including +0.022 Spearman on STS-B and +0.037 on QQP, while remaining anchored to the frozen baseline across all seeds. Because this useful form operates on sentence pairs rather than individual sentences, the resulting model is best understood as a lightweight re-ranker over cached frozen embeddings, not a replacement single-vector embedding; we make no state-of-the-art claim. Our contribution is a controlled account of when difficulty-aware adaptation helps and when it fails, together with a pre-training diagnostic that predicts the available headroom.