Large language models (LLMs) are increasingly used in finance and economics, where prompt-based attempts against look-ahead bias implicitly assume that models understand chronology. We test this fundamental question with a series of chronological ordering tasks with increasing complexities over facts the model already knows from pre-training. Our tasks cover (1) chronological ordering, (2) conditional sorting (filter, then order), and (3) anachronism detection. We evaluate GPT-4.1, Claude-3.7 Sonnet, with and without Extended Thinking (ET), and GPT-5 across multiple reasoning-effort settings. Across models, Exact match rate drops sharply as sequences lengthen even while rank correlations stay high as LLMs largely preserve local order but struggle to maintain a single globally consistent timeline. In conditional sorting, most failures stem from the filtering step rather than the ordering step, but GPT-5 and Claude-3.7 Sonnet with Extended Thinking outshine normal models significantly. Lastly, anachronism detection is found to be the easiest task for the LLMs but performance still declines with increasingly overlapping timelines or entities. Overall, our main contribution is showing that allocating explicit reasoning budget helps with chronological ordering with GPT-5 at medium/high reasoning effort achieving flawless ordering at all lengths and perfect conditional sorting (both self-filtered and given-subset), whereas low/minimal effort degrades with longer lists, mirroring earlier models. Our findings delineate limits of current LLMs on chronological tasks, providing insights into task complexity, and demonstrate scenarios in which reasoning helps. These patterns are important for the real-time application of LLMs in finance. We release all code and evaluation templates to support full reproducibility.

As is true of many complex tasks, the work of discovering, describing, and understanding the diversity of life on Earth (viz., biological systematics and taxonomy) requires many tools. Some of this work can be accomplished as it has been done in the past, but some aspects present us with challenges which traditional knowledge and tools cannot adequately resolve. One such challenge is presented by species complexes in which the morphological similarities among the group members make it difficult to reliably identify known species and detect new ones. We address this challenge by developing new tools using the principles of machine learning to resolve two specific questions related to species complexes. The first question is formulated as a classification problem in statistics and machine learning and the second question is an out-of-distribution (OOD) detection problem. We apply these tools to a species complex comprising Southeast Asian stream frogs (Limnonectes kuhlii complex) and employ a morphological character (hind limb skin texture) traditionally treated qualitatively in a quantitative and objective manner. We demonstrate that deep neural networks can successfully automate the classification of an image into a known species group for which it has been trained. We further demonstrate that the algorithm can successfully classify an image into a new class if the image does not belong to the existing classes. Additionally, we use the larger MNIST dataset to test the performance of our OOD detection algorithm. We finish our paper with some concluding remarks regarding the application of these methods to species complexes and our efforts to document true biodiversity. This paper has online supplementary materials.