Outlook keeps popping up asking for a password and not accepting it (Part-2)

Let’s go deeper. I’ll break this down into root cause areas with advanced diagnostics and fixes tailored for Outlook password prompt loops.

---

🧠 DEEP DIVE: Outlook Keeps Asking for Password – Advanced Fixes

---

🧱 1. Autodiscover + Authentication Flow Breakdown

Outlook uses Autodiscover to locate and configure the mailbox. Any misstep here = auth failure.

✅ Diagnostic Steps:

• Run this in Command Prompt: bashCopyEditoutlook.exe /autodiscover /cleanserverrules
• Or use Microsoft Remote Connectivity Analyzer: https://testconnectivity.microsoft.com/

🛠️ Fixes:

• Corrupt autodiscover entries:
  • Check: bashCopyEditregedit → HKEY_CURRENT_USER\Software\Microsoft\Office\<XX>\Outlook\AutoDiscover
  • Clear these:
    • ExcludeScpLookup, ExcludeHttpsRootDomain, ExcludeSrvRecord, etc.
    • Set them all to 0 to re-enable defaults unless explicitly set by org.
• Flush DNS + restart networking: bashCopyEditipconfig /flushdns netsh int ip reset

---

🔐 2. Modern Auth / OAuth Conflicts (Office 365, Gmail, etc.)

💡 Symptoms:

• Password loop but works in browser
• App password works but regular one doesn’t
• MFA enabled

✅ Fixes:

Office 365:

• Ensure Modern Authentication is enabled:
  • Run PowerShell (with ExchangeOnlineManagement module): powershellCopyEditConnect-ExchangeOnline Get-OrganizationConfig | FL OAuth* You want OAuth2ClientProfileEnabled : True
• Check registry: bashCopyEditregedit → HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Common\Identity Add or set: iniCopyEditEnableADAL = 1 (DWORD) And: pgsqlCopyEditHKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Common\Identity\EnableADAL = 1 HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Common\Identity\Version = 1

Gmail IMAP:

• You must use an App Password if 2FA is enabled.
• Google blocks insecure apps unless specifically allowed.

---

📦 3. Credential Manager Corruption / SSO Conflict

Even after clearing credential manager, tokens can persist or loop.

✅ Kill all tokens:

• Delete from:
  • Credential Manager
  • %LOCALAPPDATA%\Microsoft\IdentityCache
  • %LOCALAPPDATA%\Microsoft\Outlook\RoamCache
• Kill AAD tokens: powershellCopyEditdsregcmd /leave
• Rejoin AAD (if corporate): powershellCopyEditdsregcmd /join

---

💼 4. Hybrid/AADJ Issues (Work Devices)

On corporate-managed devices, you may get mismatches between:

• Device not properly joined to Azure AD
• Conditional Access Policies failing silently

✅ Fix:

• Run: powershellCopyEditdsregcmd /status
• Look for:
  • AzureAdJoined: YES
  • DeviceId present
  • SSO State: YES

If not, fix the AAD join. May need re-registering the device:

bashCopyEditSettings → Accounts → Access work or school → Disconnect and reconnect

---

🧪 5. Test Profile With Clean Flags

Create a new Outlook profile with full logging:

bashCopyEditoutlook.exe /profiles /logonprofile "<ProfileName>" /rpcdiag

You can also enable Outlook logging:

• File → Options → Advanced → Enable troubleshooting logging (under “Other”)

---

📊 6. Use SaRA with Full Traces

Use Microsoft’s Support and Recovery Assistant (SaRA):

• Choose “Outlook keeps prompting for password”
• Run trace diagnostics
• Download: https://aka.ms/SaRA-OutlookPwd

---

🚫 7. Third-Party Interference

Common offenders:

• Antivirus scanning Outlook data files
• VPNs affecting port 443 or redirecting auth URLs
• Proxy settings breaking Modern Auth

✅ Fix:

• Temporarily disable AV/firewall
• Try Outlook without VPN
• Run: bashCopyEditinetcpl.cpl → Connections → LAN Settings Ensure no unexpected proxy.