# Keith leaves DigitalOcean one site at a time

> Keith moves apps from DigitalOcean to UpCloud one site at a time to avoid hosting chaos.
- Title: Keith leaves DigitalOcean one site at a time · Keith
- Summary: Keith moves apps from DigitalOcean to UpCloud one site at a time to avoid hosting chaos. Moving hosting projects incrementally reduces migration stress.
- Keywords: keith, digitalocean, upcloud, deploy, railpack, docker, postgresql, object storage, glitch, seahawks, technology, startups
- Source: Keith — https://keith.is/post/leaving-digitalocean
- Published: 2026-09-09T00:00:00+00:00
- Read time: 1 min
- Topics: keith, digitalocean, upcloud, deploy, railpack, docker, postgresql, object storage, glitch, seahawks, technology, startups
## DigitalOcean pledge
Keith pledged $1 million yearly to the Omacom Foundation, the nonprofit behind DHH’s Omarchy.

> Three million dollars. Ten times what made me cancel 1Password.
## Why move hosting
Keith moved apps from DigitalOcean droplets and Fly machines to UpCloud for cost and global server access.

> I went in fully prepared to use the ugliest, weirdest host on the internet if the price was right.
## Deploy tool
Keith built Deploy, an open-source tool using Docker and Railpack for automatic Git deployments.

> It sits on top of Docker and Railpack, Railway’s open source build system.
## Data migration
Keith moved databases and persistent directories one site at a time to avoid overwhelming complexity.

> The actual inventory was messier than that sounds.
## Tradeoff
Keith’s setup uses one server for all apps, risking downtime if the server fails.

> The tradeoff is obvious: if that one app machine goes down, everything on it goes down with it.
## Open source?
Keith won’t open source Deploy due to its specific configuration needs for his workflow.

> It’s also built extremely specifically for me.
## One site at a time
Keith recommends moving hosting projects incrementally to reduce migration stress.

> If you’re looking at your DigitalOcean bill feeling how I felt about 1Password: you don’t have to solve the whole migration today.
## Key takeaway

Moving hosting projects incrementally reduces migration stress.