Library dependencies in software ecosystems play a crucial role in the development of software. As newer releases of these libraries are published, developers may opt to pin their dependencies to a particular version. While pinning may have benefits in ensuring reproducible builds and avoiding breaking changes, it bears larger risks in using outdated dependencies that may contain bugs and security vulnerabilities. To understand the frequency and consequences of dependency pinning, we first define the concepts of stale and fresh pins, which are distinguished based on how outdated the dependency is relative to the release date of the project. We conduct an empirical study to show that over 60% of consumers of popular Maven libraries contain stale pins to their dependencies, with some outdated versions over a year old. These pinned versions often miss out on security fixes; we find that 10% of all dependency upgrades in our dataset to the latest minor or patch version would reduce security vulnerabilities. We prototype an approach called Pin-Freshener that can encourage developers to freshen their pins by leveraging the insight that crowdsourced tests of peer projects can provide additional signal for the safety of an upgrade. Running Pin-Freshener on dependency upgrades shows that just 1-5 additional test suites can provide 35-100% more coverage of a dependency, compared to that of a single consumer test suite. Our evaluation on real-world pins to the top 500 popular libraries in Maven shows that Pin-Freshener can provide an additional signal of at least 5 passing crowdsourced test suites to over 3,000 consumers to safely perform an upgrade that reduces security vulnerabilities. Pin-Freshener can provide practical confidence to developers by offering additional signal beyond their own test suites, representing an improvement over current practices.