Keith leaves DigitalOcean one site at a time

Keith moves apps from DigitalOcean to UpCloud one site at a time to avoid hosting chaos.

Sep 9, 2026

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Keith leaves DigitalOcean one site at a time

Keith moves apps from DigitalOcean to UpCloud one site at a time to avoid hosting chaos.

In brief

Keith moves apps from DigitalOcean to UpCloud one site at a time to avoid hosting chaos. Moving hosting projects incrementally reduces migration stress. Originally reported by Keith.

Quick answers

Open source?
Keith won’t open source Deploy due to its specific configuration needs for his workflow.
What is the key takeaway from Keith leaves DigitalOcean one site at a time?
Moving hosting projects incrementally reduces migration stress.

DigitalOcean pledge

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

The Deploy dashboard listing my running apps

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.”

Here's the gist

Moving hosting projects incrementally reduces migration stress.

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