Experimentally, updates to the "core" packages used by DSS (pandas, scikit-learn, jupyter, ...) are likely to break something.
At the moment, DSS 2.3 is known not to work properly with newer Pandas (behavior changes on dates), and scikit-learn (API change). For Jupyter, note that DSS uses a patched version of the "notebook" package, installing an updated pristine API change will make the integration at least partly non functional.
The more stable packages like requests or numpy are less dangerous (but there is also less incentive to update)
We'll probably update pandas and scikit learn in the next DSS update end of March