Fixing OneDrive Asking for Login on Every Windows Startup

Have you ever found yourself repeatedly logging into OneDrive every time your Windows PC starts, even though you just signed in the last session? You’re not alone. This is a common problem for both personal and enterprise users of Microsoft 365. Fortunately, this issue can be resolved by identifying its root causes and applying the right solutions.

In this post, I’ll walk you through step-by-step troubleshooting to stop OneDrive from prompting for login every time your PC boots up.

---

🧠 Why Does OneDrive Keep Asking Me to Sign In?

This issue typically occurs due to:

• Corrupted or outdated cached credentials
• Incomplete browser-based authentication
• Disabled auto-start settings for OneDrive
• A corrupted OneDrive installation or sync issues
• Group Policy or registry restrictions (especially in corporate environments)
• Network trust/authentication issues

Let’s troubleshoot each of these possibilities.

---

✅ Step-by-Step Troubleshooting Guide

1. 🔐 Sign in via Default Browser at Least Once

OneDrive often relies on a browser-based authentication flow to maintain your login session—especially in environments using Azure AD or Microsoft 365. If you haven’t signed in through your default browser, OneDrive might struggle to persist your login.

Steps:

1. Open your default browser (e.g., Microsoft Edge, Chrome).
2. Navigate to https://onedrive.live.com.
3. Sign in with the same Microsoft account used in OneDrive.
4. When prompted, check “Keep me signed in”.
5. Close the browser and restart your PC.

This small but crucial step helps OneDrive authenticate properly across system sessions.

---

2. 🗝️ Clear Cached Credentials

Corrupted or outdated credentials stored in Windows Credential Manager can break your OneDrive session.

Steps:

1. Open Credential Manager via Start menu.
2. Select Windows Credentials.
3. Look for entries like:
   • OneDrive Cached Credential
   • MicrosoftOffice16_Data:SSPI
   • microsoftonline.com entries
4. Remove those credentials.
5. Restart and re-sign in to OneDrive when prompted.

---

3. ⚙️ Verify OneDrive Auto Start Settings

If OneDrive isn’t set to auto-start properly, it may not retain your session.

Steps:

1. Right-click the OneDrive cloud icon in the taskbar.
2. Click Settings.
3. Under the Settings tab, make sure Start OneDrive automatically when I sign in to Windows is checked.
4. Click OK and reboot.

---

4. 🚑 Repair or Reinstall OneDrive

A corrupt installation or outdated version could also be to blame.

Steps:

1. Download the latest OneDrive version: https://www.microsoft.com/en-us/microsoft-365/onedrive/download
2. Uninstall OneDrive via Settings > Apps > Installed apps.
3. Reinstall using the latest installer.
4. Launch OneDrive and log in again.

---

5. 🧽 Reset OneDrive Completely

Resetting OneDrive clears the local configuration without removing files.

Steps:

1. Press Win + R, then run: shellCopyEdit%localappdata%\Microsoft\OneDrive\onedrive.exe /reset
2. If OneDrive doesn’t restart automatically, run: shellCopyEdit%localappdata%\Microsoft\OneDrive\onedrive.exe
3. Re-sign in and reselect your sync folders if prompted.

---

6. 🪟 Apply Registry Fixes (Advanced)

Be cautious—editing the registry incorrectly can cause issues. Back up before proceeding.

Steps:

1. Open the Registry Editor (regedit).
2. Navigate to: CopyEditHKEY_CURRENT_USER\Software\Microsoft\OneDrive
3. Delete the UserFolder key if it exists.
4. Then go to: sqlCopyEditHKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Common\Identity
5. Delete subkeys related to identity or sign-in persistence.
6. Restart your PC.

---

7. 🛡️ Check Group Policy and Domain Settings (For IT Admins)

In domain-joined environments, policy restrictions can override OneDrive settings.

Steps:

1. Run gpedit.msc.
2. Navigate to: nginxCopyEditComputer Configuration > Administrative Templates > Windows Components > OneDrive
3. Ensure Prevent the usage of OneDrive for file storage is Not Configured.
4. Check under: pgsqlCopyEditUser Configuration > Administrative Templates > System > Logon for settings like Always wait for the network at computer startup and logon.

---

8. 🌐 Ensure Network Trust & Connectivity

Authentication relies on proper network setup. If you’re on a public or metered network, OneDrive may not authenticate at boot.

Checklist:

• Change your network type to Private.
• Temporarily disable firewall/antivirus to test.
• Whitelist Microsoft domains: markdownCopyEdit*.onedrive.com *.live.com *.microsoftonline.com *.sharepoint.com

---

9. 🔍 Use Event Viewer for Deeper Insight

OneDrive errors are often logged to Event Viewer.

Steps:

1. Press Win + R, type eventvwr.msc, press Enter.
2. Go to Windows Logs > Application.
3. Look for entries with sources like OneDrive, User Profile Service, or Office16.

A persistent OneDrive login prompt can be disruptive, but thankfully, it’s often easy to fix once you address the right root cause. Start with the simplest checks—like signing in via the browser—then move toward more advanced fixes such as credential cleanup, Group Policy review, or full reset.

By methodically working through the steps in this guide, you should be able to resolve the issue and ensure that OneDrive works smoothly with each reboot.