I would rather work with a company that updates continuously, while also building security into multiple layers so that weaknesses in one layer can be mitigated by others.
For example, at one company I worked for, they created an ACL model for applications that essentially enforced rules like: “Application X in namespace A can communicate with me.” This ACL coordinated multiple technologies working together, including Kubernetes NetworkPolicies, Linkerd manifests with mTLS, and Entra ID application permissions. As a user, it was dead simple to use and abstracted away a lot of things i do not know that well.
The important part is not the specific implementation, but the mindset behind it.
An upgrade can both fix existing issues and introduce new ones. However, avoiding upgrades can create just as many problems — if not more — over time.
At the same time, I would argue that using software backed by a large community is even more important today, since bugs and vulnerabilities are more likely to receive attention, scrutiny, and timely fixes.