Dropstone Docs

Common issues

Fix common Dropstone CLI install and runtime issues. Step-by-step solutions for failed installs, auth problems, and update errors.

The most common issues Dropstone users hit, with the steps to fix them. For runtime errors and per-feature debugging, see the CLI troubleshooting page.

Install fails on macOS

"Command not found: brew"

You need Homebrew first. Install it once:

/bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)"

On Apple Silicon, also add Homebrew to your PATH:

echo 'eval "$(/opt/homebrew/bin/brew shellenv)"' >> ~/.zprofile
eval "$(/opt/homebrew/bin/brew shellenv)"

Then re-run the Dropstone install:

brew tap blankline-org/dropstone-cli
brew install dropstone

"Cannot install: package already exists"

Force-overwrite the existing install:

brew uninstall dropstone
brew install dropstone

Homebrew tap fails to refresh

Clear the cache and re-tap:

brew untap blankline-org/dropstone-cli
brew cleanup
brew tap blankline-org/dropstone-cli
brew install dropstone

Install fails on Windows

"irm is not recognized as an internal or external command"

You're in CMD, not PowerShell. Either switch to PowerShell:

irm https://dropstone.io/install.ps1 | iex

Or use the CMD installer:

curl -fsSL https://dropstone.io/install.cmd -o install.cmd && install.cmd

"The token '&&' is not a valid statement separator"

You're in PowerShell trying to run the CMD command. Switch to the PowerShell one above.

Pending update did not apply

If dropstone update reported success but dropstone --version still shows the old version, restart your terminal. On Windows the new binary swaps in on next launch.

If that still doesn't help, force-reinstall:

irm https://dropstone.io/install.ps1 | iex

Authentication

"Failed to sign in"

  1. Run dropstone again. On first launch it opens dropstone.io/login for PKCE-based sign-in.
  2. If the browser flow fails, paste a token instead. Grab one at dropstone.io/account and choose "Paste a token" at the sign-in prompt.

"Session expired"

Run /login from inside Dropstone to refresh your credentials.

Stuck on the wrong account

To switch accounts, run /login from inside Dropstone and pick the right account at the browser prompt.

Update problems

dropstone update reports "Update Available" but does nothing

This usually means the auto-installer doesn't have write access to the binary's directory. Reinstall using your original method:

PlatformCommand
macOS (Homebrew)brew upgrade dropstone
macOS / Linux (script)curl -fsSL https://dropstone.io/install | bash
Windows (PowerShell)irm https://dropstone.io/install.ps1 | iex

Stuck on an old version

Check what's installed:

dropstone --version

Compare against the latest at download.dropstone.io/latest.txt. If they don't match, reinstall using the platform command above.

Still having issues?

If none of the above resolved your problem, see the more detailed CLI troubleshooting page, or open an issue at dropstone.io/contact with:

  • Your OS and version
  • The output of dropstone --version
  • The full error message and the exact command you ran
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