What stopped you from hesitating when raising prices on early adopters?

When I launched I just picked a price below a couple of competitors without really looking at long term math. Six months in between hosting costs and hours spent answering tickets I'm essentially working for free.

Grandfathering old users or adding higher tiers makes sense on paper but actually communicating the change to people who signed up early feels extremely awkward.

If you had to fix underpriced software after launch what made writing that announcement email easier?