From Flat to Fragmented: The New Reality of Overlay Routing

From Flat to Fragmented: The New Reality of Overlay Routing

From Flat to Fragmented: The New Reality of Overlay Routing

What has happened to the promise of security and ease with the “simple, flat network” we thought we had achieved through the elimination of WAN complexity, and was it the right idea in the first place? As Tailscale deployments quietly take control of routing on our endpoints, a familiar set of challenges is re-emerging—but in stranger, harder-to-debug forms.

Why do cloud environments commandeer massive CIDR blocks that swallow everything in their path? And why are engineers once again reaching for tools and mental models that feel suspiciously like early-2000s enterprise networking?

Let's unpack the subtle but profound shift from network-defined topology to endpoint-driven routing, reveal patterns you may already be encountering without realizing it, and hint at the architectural moves that can keep your network from tying itself in knots.