Troubleshooting

Common issues and how to fix them.

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Finder

"Send to R2" is missing from the right-click menu

Finder Sync extensions are cached aggressively by macOS.

1. Go to System Settings → Privacy & Security → Extensions → Finder Extensions

2. Toggle the R2Drop extension off, then back on

3. Run killall Finder in Terminal

If it still doesn't appear, quit R2Drop completely and relaunch it.

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Upload Issues

Uploads are stuck on "Pending"

• Check that your account has a bucket configured — open the Accounts tab and verify the bucket field is not empty

• Check R2 connectivity: r2drop status

• If the macOS app is not running, the upload engine won't process the queue — launch the app

Upload failed with a network error

R2Drop retries automatically with exponential backoff (up to 10 retries). If all retries fail:

1. Check your internet connection

2. Verify your API token is still valid: r2drop status

3. Re-run the upload

has no bucket configured

Open Accounts tab in the app and fill in the Bucket field for your account.

From the CLI, edit ~/.r2drop/config.toml and set the bucket field under the relevant [[accounts]] entry.

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Authentication

No token for ... / Keychain errors

Your API token was not found in the macOS Keychain.

r2drop login   # Re-authenticate interactively

If issues persist, open Keychain Access.app, search for com.superhumancorp.r2drop, and delete any stale entries before logging in again.

Token expired or revoked

R2Drop checks token validity on launch. If the token has been revoked in the Cloudflare dashboard:

1. Create a new API token in Cloudflare → My Profile → API Tokens

2. Run r2drop login and paste the new token, or use Accounts tab → Update Token

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CLI

r2drop: command not found

The binary is not in your PATH.

echo 'export PATH="$HOME/.local/bin:$PATH"' >> ~/.zshrc
source ~/.zshrc

Verify the install:

r2drop --version

No account specified or Account not found

r2drop accounts                         # List configured accounts
r2drop accounts --switch "My Account"   # Set active account

Rust toolchain errors when building from source

The install script builds from source and requires a modern Rust stable toolchain.

rustup update stable
./scripts/install-cli.sh --prefix ~/.local

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App Behavior

R2Drop doesn't appear in the Dock

If you've enabled Hide Dock Icon in Settings, the app only shows in the menu bar. To restore the Dock icon:

1. Click the menu bar icon → Preferences → Settings

2. Uncheck Hide Dock Icon

Or from the CLI:

r2drop config set hide_dock_icon false

No sound on upload complete

Check that Play sound on complete is enabled in Settings tab, and that your Mac's volume is not muted.

Auto-updates not working

Open About tab → Check Now to manually trigger an update check.

If updates are blocked, verify that R2Drop has outbound network access in System Settings → Network → Firewall.

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Resetting R2Drop

To start fresh and reset all local state:

rm -rf ~/.r2drop

This removes all accounts, queue, history, and config. Your files in R2 are not affected.

You'll need to go through onboarding again after this.

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Still Stuck?

Open an issue on GitHub with:

• Your macOS version

• R2Drop version (from About tab)

• Steps to reproduce

• Any relevant output from r2drop status --json