5 Files You're Forgetting to Back Up (And Will Regret Losing)

By Alex Morgan, Cloud Solutions Architect
Last Updated: May 2026 · 7 min read

Everyone backs up Documents and Photos. But here are five categories of files I've personally lost — and watched friends lose — over the years. Files that, once gone, you can't recreate. Files that backup guides never mention.

1. Browser Bookmarks & Passwords

A former colleague lost 10 years of bookmarks when his laptop died. He had backed up his Documents and Photos religiously. His bookmarks — years of research, client resources, tools — vanished overnight. Export bookmarks as HTML (Chrome: Bookmark Manager → Export bookmarks). Better yet, use a password manager that syncs (see our free password manager guide) so you don't rely on browser saved passwords at all.

2. Application Settings & Config Files

Your VS Code extensions, terminal aliases, Alfred workflows, AutoHotkey scripts — these are tiny files that represent hundreds of hours of customization. I once reinstalled Windows and spent six hours trying to remember every config tweak. Now I back up ~/.config (Mac/Linux) and %APPDATA% (Windows) with Restic. Even better, version-control your dotfiles with Git and push to a private repo.

3. Chat Histories (WhatsApp, Signal, Telegram)

My mother lost three years of WhatsApp conversations with her sister when she switched phones. Back up WhatsApp to Google Drive or iCloud. Signal offers encrypted backups in settings. Telegram stores chats in the cloud, but exports are manual. Losing conversations with loved ones is a different kind of data loss — one that can't be measured in gigabytes. Monthly chat backups take 30 seconds.

4. Email Archives

If you use Gmail or Outlook.com, your emails are in the cloud — fine. But if you use a desktop client (Thunderbird, Apple Mail, legacy Outlook) with local PST or profile folders, those files are one hard drive crash from oblivion. Export important emails as PDF or .eml files and include them in your backup routine. I archive client project discussions and invoices annually to PDF.

5. Digital Licenses & Receipts

Software licenses, domain registration receipts, SSL certificate orders, and proof of purchase for tax deductions — these come via email and get buried. Create a folder called "Receipts" in your cloud storage and save every confirmation there. Forward email receipts to that folder. When tax season arrives, you'll thank yourself.

One-Click Backup Checklist

  1. Export browser bookmarks → save .html to your cloud backup folder.
  2. Copy config folders → add ~/.config or %APPDATA% to your automated backup script (see our cloud backup guide).
  3. Export chat histories → WhatsApp (Settings → Chats → Chat backup), Signal (Settings → Chats → Chat backups), Telegram (Desktop → Settings → Advanced → Export Telegram data).
  4. Archive important emails → save as PDF to your Receipts folder.
  5. Save receipts & licenses → create a dedicated cloud folder and forward all confirmation emails there.

Now schedule all of this with Restic, Rclone, or your automated backup system. Once set, you'll never think about it again — until the day you need it.

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Have a file type you think belongs on this list? Reach us at contact@viperstream.cloud.