OneDrive File Issues

How to Fix OneDrive Upload Failed and Sign-In Problems on Mac

Maira Mehtab Sep 28, 2026 868 views

Question details

The user is experiencing recurring OneDrive upload failures, OneNote connection errors, sign-in problems, and web download issues across multiple Macs and Microsoft accounts.

Product: Microsoft OneDrive
Device & OS: Mac
Scenario: Attempting to sync files to OneDrive or sign in to Microsoft services on a Mac computer.
Observed behavior: OneDrive uploads repeatedly fail and sign-in issues persist, even after attempting temporary workarounds like switching networks, changing DNS settings, and clearing Keychain credentials.

Before you start

Ensure your Mac is connected to a stable internet network and verify the Microsoft 365 Service Status page online to rule out any widespread server outages before proceeding.

Solution 1Recommended

Flush the Mac DNS Cache

Clearing the local DNS cache can resolve persistent network routing issues that block OneDrive from communicating with Microsoft servers.

If changing networks or DNS settings temporarily resolves the problem, the local DNS cache on your Mac might be corrupted. Flushing it forces your system to fetch fresh DNS records.

Open Terminal

Navigate to Applications > Utilities on your Mac and launch the Terminal application.

Execute Flush Command

Type 'sudo dscacheutil -flushcache; sudo killall -HUP mDNSResponder' into the Terminal window and press Enter.

Enter Administrator Password

When prompted, type your Mac administrator password (characters will not appear as you type) and press Enter.

Restart Mac and Test

Reboot your Mac, open OneDrive, and attempt to sign in and upload your files again.

Terminal Executed: A successful DNS flush will not display a confirmation message; the command prompt will simply appear on a new line.

Solution 2

Check Firewall, Proxy, and Security Settings

Temporarily disabling network security features helps determine if a firewall or proxy is blocking OneDrive's background syncing processes.

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Frequently Asked Questions

Why does my OneDrive upload keep failing on Mac?

Upload failures are often caused by corrupted local DNS caches, network proxy misconfigurations, overly strict firewall rules, or temporary Microsoft server outages.

How do I clear Keychain credentials for OneDrive?

Open Spotlight Search (Cmd + Space), type 'Keychain Access', search for 'OneDrive', delete the related credential entries, and then restart the OneDrive application to sign in fresh.

Does changing DNS servers fix OneDrive sync issues?

Yes, switching your Mac's DNS settings to public DNS servers like Google DNS (8.8.8.8) or Cloudflare (1.1.1.1) can bypass ISP-level routing issues that may be blocking access to OneDrive servers.

Document & File Issues