How to migrate a Windows server to Cloudflare R2

Moving from a Windows server to Cloudflare R2 usually means a script somebody wrote once and a weekend of watching it. This job replaces the script: it copies everything, resumes if interrupted, and can be run again right before the switch to catch what changed.

This job runs on the Business plan (Cloudflare R2 and Google Cloud Storage buckets, Azure sources and server destinations are Business features). Every account starts with a 14-day trial of Pro; see plans.

1. 1.Connect the source. Enable the built-in OpenSSH Server on Windows (Settings → Apps → Optional features), then under Credentials → Servers add the machine with a user and its password or key. Paths are written the Windows way, C:\Data\Exports, and BucketPilot connects from one fixed address, 3.111.107.194.
2. 2.Connect the destination. Create an R2 API token with Object Read & Write on the Cloudflare dashboard and add it under Credentials. Then import the bucket under Buckets & Servers, or create one there.
3. 3.Open Backups & Migrations and press Create. Choose A server as the source and A bucket as the destination, then Continue.

1. 1.Pick the server and type the source path — the folder whose contents you want, for example /var/www/uploads or C:\\Exports. Tick *put the folder itself in the destination* if you want the folder name kept.
2. 2.Pick the destination bucket and, if you like, a folder inside it where the files land.
3. 3.Leave the schedule on manual for a one-time move, or set one if the source keeps receiving files and you want them to follow. Choose how many files copy in parallel (threads); eight is a good default for a busy server.

1. 1.Press Create Job, then Run now. The first run copies everything; every run after it copies only what changed.

Every run is incremental: a file is copied only if its size or timestamp differs from the copy, so a nightly run of a large source moves only the day's changes and finishes in minutes.

Files are streamed from source to destination — multi-gigabyte files never sit in memory, and a run that is paused or loses its worker resumes where it stopped.

You can watch it: live progress on the job, a per-file log, and an email when a run finishes or needs attention. Transient errors retry with backoff; a run that fails outright is reported, never silently skipped.

Cloudflare R2 has no object versioning, so the copy holds the latest version of each file. Nothing is ever deleted at the destination by a backup, so a file removed at the source stays in the copy until you remove it yourself.

Every job has a Restore button: it copies from the destination back to the source, only what is missing there, never overwriting a newer file and never deleting anything. A backup you cannot restore from is not a backup, so this is part of the job, not a separate product.