Outlook Keeps Asking for Password? Fix Persistent Prompts (2025 Guide)

Outlook Issues • Oct 25, 2025

Outlook Keeps Asking for Password (Even After Entering It) — Complete Fix Guide (2025)

If Microsoft Outlook keeps asking for your password repeatedly, even after you’ve entered the correct credentials, you’re likely facing a mix of cached credentials, authentication policy, or profile corruption issues. This step-by-step guide walks you through proven fixes for Outlook with Microsoft 365, Exchange, IMAP/POP, and hybrid accounts so you can sign in once and stay signed in.

Typical Reasons Outlook Repeatedly Prompts for a Password

  • Old or conflicting credentials stored in Windows Credential Manager
  • Outdated profile or corrupted local mail cache (OST/PST)
  • Modern Authentication (OAuth) disabled or misconfigured
  • MFA (two-step verification) not completing or app password required
  • Basic Auth still enabled on older setups (causing loops)
  • Broken Trusted Platform Module (TPM) or Web Account Manager sign-in cache
  • Antivirus / firewall or proxy interfering with secure sessions
  • IMAP/POP accounts with incorrect server/port/SSL settings

Quick Wins (Try These First)

  1. Restart Outlook and Windows (flushes temporary sign-in caches).
  2. Confirm the actual account password by logging into Outlook Web (OWA). If the password doesn’t work there, reset it.
  3. Update Outlook: File → Office Account → Update Options → Update Now.

Fix 1 — Clear Old Passwords in Windows Credential Manager

Stale cached credentials are the #1 reason for looping prompts.

  1. Close Outlook.
  2. Open Credential Manager (Windows Search → “Credential Manager”).
  3. Go to Windows Credentials.
  4. Remove entries for:
    • MicrosoftOffice16_Data:ADAL, MicrosoftOffice15/16, Outlook, ADAL, or entries containing your email/domain.
  5. Reopen Outlook and sign in once when prompted.

Fix 2 — Verify Modern Authentication & MFA

Microsoft 365 uses Modern Authentication (OAuth). If it’s disabled, Outlook may fall back to Basic Auth (often blocked) and keep prompting.

  • For Microsoft 365 tenants, ensure Modern Auth is enabled in the admin center.
  • If MFA is enabled, complete the pop-up prompt or use the Microsoft Authenticator app.
  • For older IMAP/POP connections on accounts with MFA, you may need an App Password from the provider’s security page.

Fix 3 — Repair or Recreate the Outlook Profile

Corrupted profiles cause repeated password prompts and sync failures.

  1. Close Outlook.
  2. Open Control Panel → Mail → Show Profiles.
  3. Select your profile → Repair. If that doesn’t help:
  4. Click Add → create a new profile → set it as Always use this profile.

Tip: Enable Cached Exchange Mode for faster, more reliable sign-in: File → Account Settings → Account → Change → “Use Cached Exchange Mode”.

Fix 4 — Reset Sign-In Components (WAM/ADAL) & WebView

Outlook relies on Windows sign-in components. Resetting them often stops loops.

  1. Close Outlook and all Office apps.
  2. Open Windows Settings → Accounts → Access work or school → disconnect stale work accounts (if present), then re-add.
  3. Open Edge (or your default browser) and sign out of your Microsoft account, then sign back in.
  4. Ensure WebView2 Runtime is installed and updated (required for modern sign-in UI).

Fix 5 — Delete Cached Tokens & Re-Authenticate

Sometimes Outlook stores broken token files. Clearing them helps.

  1. Close Outlook.
  2. Delete the folder contents (not the folder) at:
    %localappdata%\Microsoft\IdentityCache and %localappdata%\Microsoft\Office\16.0\Wef
  3. Restart Outlook and complete sign-in.

Fix 6 — Check Server, Ports, and SSL (IMAP/POP/SMTP)

Incorrect mail servers or ports will force Outlook to ask for credentials repeatedly.

  • IMAP: 993 (SSL/TLS), POP: 995 (SSL/TLS)
  • SMTP: 587 (STARTTLS)
  • Hostnames for Microsoft 365: outlook.office365.com (IMAP/POP), smtp.office365.com (SMTP)

Update saved settings via File → Account Settings → Server Settings. Use your full email as the username.

Fix 7 — Disable Problematic Add-ins & Security Software

  1. Open Outlook in Safe Mode: press Win + R → type outlook /safe → Enter.
  2. If prompts stop, disable add-ins: File → Options → Add-ins → Manage COM Add-ins → Go → uncheck non-Microsoft add-ins.
  3. Temporarily disable antivirus email scanning; ensure your firewall allows Outlook and secure mail ports.

Fix 8 — Reset Network Stack & DNS

If the issue follows you across devices, network policies or cached DNS can be the culprit.

ipconfig /flushdns
ipconfig /registerdns
netsh winsock reset
netsh int ip reset

Restart your PC and try Outlook again.

Fix 9 — Windows Work/School Account Re-Join (Work PCs)

On managed devices, broken work account tokens cause Outlook loops.

  1. Settings → Accounts → Access work or school → Disconnect the account.
  2. Restart → re-join the account → open Outlook → complete MFA.

Fix 10 — When to Use an App Password

If your provider uses MFA and you’re connecting via IMAP/POP in Outlook, the normal password may fail. Generate an App Password from your account’s security page and use it in Outlook’s incoming/outgoing password fields.

Prevention Checklist

  • Keep Outlook and Windows updated monthly
  • Use Modern Auth (OAuth) wherever possible
  • Avoid mixing Basic Auth with MFA
  • Don’t let multiple stale profiles/accounts linger in Windows
  • Back up OST/PST before major updates or profile changes

Need Help?

If Outlook still asks for your password after these steps, our experts can diagnose remote sign-in loops and fix profile/authentication problems for you. Contact FixTechGuide for quick assistance.

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