The context around that sentence does quite explicitly intends to insure the outcomes because you can't really ensure it. I mean, the paragraph literally starts with "Insurance as code”.
If you're talking about the language, insurance is wrong: retries do ensure positive outcomes. However, assurance is wrong as well: unlike retries, observability tools don't ensure positive outcomes, they just mitigate the negative ones.
It's just bad writing, using a tortured metaphor to explain a definition that doesn't make any sense.