Detecting Invalid Characters and Long Paths in OneDrive on macOS

Microsoft OneDrive is widely used for syncing documents across devices, but on macOS, it can silently fail to sync certain files if they violate Windows filesystem rules — like overly long paths or invalid characters. This creates frustrating experiences for end users who don’t know why files aren’t syncing.

To address this issue, I created a script — check_onedrive_paths.zsh — which detects common pathing issues and logs them to a file for JAMF or local review.

🔍 What the Script Does

This Zsh-based script is designed to scan a user’s OneDrive directory and:

• 🚫 Detect filenames with Windows-incompatible characters (like *, :, ?, |, etc.)
• 📏 Identify file paths exceeding the maximum path length (400 characters)
• 🔠 Flag individual filenames that exceed macOS filesystem length limits (255 characters)
• 🪄 Optionally shorten long filenames automatically to prevent sync issues

A log file is written to /Users/Shared/onedrive_path_check.log and displayed at the end of the run for JAMF integration.

📁 How It Works

1. Defines Limitations:
   • Max path length: 400
   • Max filename length: 255
   • Invalid characters defined as a pattern: [*:<>?/\\|"]

2. Looks Up the Logged-In User: Uses stat -f %Su /dev/console to find the current user and determine their OneDrive directory path.

3. Recursively Scans Files: Uses find to inspect all files in the OneDrive directory and:
   • Reports invalid characters
   • Logs overly long paths
   • Shortens names if the shorten_filename() function is triggered
4. Outputs a Log: The log summarizes every issue found, making it easy for IT to take action.

🛠 Example Output

OneDrive Path Check - Mon Jul 14 10:23:45 EDT 2025
Invalid characters: /Users/jon/Library/CloudStorage/OneDrive/file:backup.docx
Path too long (405 chars): /Users/jon/Library/CloudStorage/OneDrive/very/deep/nested/folder/structure/that/keeps/going/on/and/on...
Filename too long (280 chars): /Users/jon/Library/CloudStorage/OneDrive/photos/this_is_a_very_very_very_very_long_filename_that_should_probably_be_shortened.jpg

⚠️ Why This Matters

Microsoft OneDrive follows stricter pathing and filename rules due to its underlying Windows-based architecture. macOS doesn’t naturally enforce these, so users can create files that OneDrive won’t sync — with no clear error message.

This script provides an automated way to detect and optionally fix these issues, ideal for use in:

• JAMF Pro policies
• IT onboarding scripts
• Scheduled maintenance routines

🔄 Customization

You’ll want to modify this section of the script to match your OneDrive setup:

ONEDRIVE_FOLDER_NAME=""

Replace with your folder name (e.g., "OneDrive - CompanyName").

You can also tune the limits or logging path to suit your environment.

📎 Get the Script

👉 check_onedrive_paths.zsh

Keep your users syncing smoothly — and OneDrive compliant — by proactively checking for path issues!

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