Backdating does not seem very friendly with current nostr infra or clients.. you'll need a new client..
Just ive noticed clients use timestamps a lot to limit their reqs.. and tend to be very timeline centric. They won't usually see old notes. Tho that doesn't explain why they can't pull a specific eventID from a specific outbox. Relays also can tend to limit old messages, unless they're serving backups capability, so that would make it important that the outbox gitlost uses supports very oldness.