Whilst TS does technically contain breaks, these are normally simple increases in the power of the type-checking. It's finding more errors in code that previous seemed fine. Think of it like adding more ESlint rules.
It's rare for there to be a breaking change in the JS emit.
The TypeScript team work hard to preserve compatibility. Breaking changes are explicitly managed and communicated ahead of time. There is a concept of a breakage-budget per-release. This means if you stay up to date, the cost of each upgrade should not be huge. Orta and Nathan on the TypeScript team talk about this in this podcast episode: https://dev.to/devteam/devnews-s1e4-typescript-4-0-gitee-chr...
The majority of breaks are due to the checker getting better. So code that passed now errors. Most of the time pre-existing published DTS files still operate fine.
Yeah, in most cases the breaks are because of how DTS files are interpreted in consuming projects, as new strictness checks light up. Most of the time that has seemed to be what the DTS files really intended and the previous interpretation less useful.
A useful example is Strict Null Checks which started to treat unadorned types as non-nullable (string versus string? versus string | null). In most cases the runtime behavior of libraries were already throwing errors when nulls were passed in, and the extra checks helped immensely. In rarer cases "oh yeah, null is totally a valid thing to send to this API and it has some defined behavior that we document/should document" and the DTS files were encouraged to annotate their types to include that. In the worst where libraries had such APIs but failed to update their DTS files, there were explicit casting workarounds in consuming projects (the awkward `null as string` and the so called "damn it" operator `possiblyNullString!`).
It's rare for there to be a breaking change in the JS emit.
The TypeScript team work hard to preserve compatibility. Breaking changes are explicitly managed and communicated ahead of time. There is a concept of a breakage-budget per-release. This means if you stay up to date, the cost of each upgrade should not be huge. Orta and Nathan on the TypeScript team talk about this in this podcast episode: https://dev.to/devteam/devnews-s1e4-typescript-4-0-gitee-chr...
So "keeping up" is not too hard.