Move a Windows file server into Amazon S3

A Windows file server holds a decade of folders that nobody has audited, some of them with paths longer than the tools that will read them. The usual approaches are a scheduled script that nobody owns, or a desktop S3 client that somebody runs by hand and forgets to run again.

Both leave the same question open: which files actually made it? A copy that reports "completed with errors" over 400,000 files is not an answer, and re-running it from the beginning to find out costs another full read of the share.

1. 1.Turn on OpenSSH Server on the Windows machine — it is an optional Windows feature, and this is the step that catches almost everyone. See Connecting your own server for the four PowerShell commands.
2. 2.Add the server under Credentials → Servers, and press Test Connection. BucketPilot detects that it is Windows on the first successful connection and applies Windows path rules from then on.
3. 3.Connect the AWS account and pick the destination bucket.
4. 4.Create a migration job with the server path as the source. The first run walks the tree and copies it; a run that dies is resumed rather than restarted.
5. 5.Re-run until cutover. Later runs copy only what changed since the last one, so the final pass before you retire the share is short.

• •OpenSSH Server is not installed by default. A healthy machine that has never had it enabled looks exactly like one that is switched off: the connection gets no answer. If a test times out, rule this out first.
• •An administrator's key does not live in that account's .ssh folder. OpenSSH on Windows reads one shared file for every account in the Administrators group, and silently ignores the per-user file. The key belongs in C:\ProgramData\ssh\administrators_authorized_keys — a key in the wrong place authenticates for nobody and produces no error anywhere.
• •Paths are written /C:/like/this throughout BucketPilot, because that is the form Windows' own SSH server prints and accepts. Type a backslash path and it is stored in that canonical form.
• •The platform is detected, not chosen. There is no operating-system dropdown; on the first successful connection the machine is asked to resolve its own working directory, and the answer decides how every path on it is separated and compared. A wrong dropdown would apply the wrong rules silently.
• •Large files are sent in parts, so a single big export does not have to succeed in one request.
• •One address to allow through the firewall. Every connection BucketPilot makes to a server comes from 3.111.107.194, so you can open your SSH port to that one address rather than to the internet.

• •No agent. Nothing is installed on the server; the connection is SSH and you can revoke it by removing the key.
• •Incremental reruns — the second and later passes carry only what changed.
• •A log per file, so "which files did not make it" has a list rather than a count.
• •Retries and resume on transient errors and on a worker that dies mid-run.
• •A schedule — hourly, daily, weekly or monthly, so the share stays in step with the bucket until you cut over.

BucketPilot connects over SSH with a key you install and can remove. Host keys are verified on first use on the Pro plan and above. Files stream from the server to the bucket during a run and no copy of their contents is kept here.

Adding and testing a server is not plan-gated; using one as a migration source is Pro, which the trial includes. Full detail: Security & privacy.

• •You are retiring a file server and the data has to live in S3 afterwards.
• •You want the share and the bucket in step for a few weeks before the switch.
• •You want an auditable record of which files moved, rather than a copy tool's summary.

When it is not. If you want files to keep arriving on the server and being copied for ever, that is a scheduled backup rather than a migration — the same job, run on a schedule, and the distinction matters when someone deletes a file and expects the bucket to keep it. If you need to pull a bucket back *down* onto a Windows machine, that direction is a Business feature.