Why Choose Keith Thomas
• 20 years of experience as a Senior Apple Support Specialist at Apple Computer UK HQ.
• Former Apple Computer UK Mac Support Specialist and Apple Authorised Service Provider background.
• Established and Independent since 2010 for on‑site Apple Support Service – no call centres, no outsourcing, no hardware repairs. Over 25,000+ Apple problems resolved. Unique on-site Apple Support Service. backed up with Independent Apple Telephone Support Assistance.
• Trusted by home users, small businesses, and professionals across London and the South East UK.• Clear, honest, software‑only support. No Hardware Repairs. Expert Apple Consultancy Service.
On‑site Apple Mac Support in London and the South East UK
What this page covers
This guide explains the real reasons Outlook for Mac keeps asking for your email password, the steps you can try yourself, and when it’s time to get professional on‑site help. It applies to:
• Microsoft 365 accounts
• Exchange accounts
• Outlook.com accounts
• Gmail, iCloud and IMAP accounts added to Outlook
If Outlook repeatedly prompts for your password, refuses to authenticate, or keeps disconnecting from your email account, this page is for you.
The most common reasons Outlook for Mac keeps asking for your password
These are the issues that Keith Thomas identifies most often during on‑site visits:
• Incorrect password
• Microsoft 365 authentication issues
• Two‑factor authentication problems
• App‑specific password required
• Keychain conflicts
• Damaged Outlook profile
• macOS update issues
• Corrupted user account
Quick checks you can do yourself
These steps solve around 60% of repeated password prompts.
Check 1 – Restart the Mac
A restart resets Outlook and authentication services.
Check 2 – Check your password
Most repeated prompts happen after password changes.
Check 3 – Approve login alerts
Microsoft, Google and Apple often require approval on another device.
Check 4 – Update macOS and Outlook
Authentication fixes are often included in updates.
If Outlook shows “Authentication Required”
This usually means:
• Incorrect password
• Authentication token expired
• Microsoft 365 security block
Try:
• Re‑entering your password
• Approving the login on your phone
• Restarting the Mac
If Outlook keeps asking for your Microsoft 365 password
This usually means:
• Microsoft 365 authentication issue
• Damaged Outlook profile
• Keychain conflict
Try:
• Signing out and back into your Microsoft 365 account
• Removing old Microsoft passwords from Keychain
• Restarting the Mac
If Gmail keeps asking for your password in Outlook
This usually means:
• Google security block
• App permissions revoked
• Two‑factor authentication required
Try:
• Approving the login on your phone
• Checking Google Account security alerts
• Restarting the Mac
If iCloud Mail keeps asking for your password in Outlook
This usually means:
• Apple Account authentication issue
• App‑specific password required
• Keychain conflict
Try:
• Generating an app‑specific password
• Restarting the Mac
• Checking Apple Account security settings
If password prompts started after a macOS update
This usually means:
• Outlook authentication reset
• Keychain reset
• Account re‑authentication required
Try:
• Re‑entering your email password
• Restarting the Mac
• Updating Outlook
If Outlook works on another user account
This usually means:
• Corrupted user account
• Damaged Outlook preferences
• Permissions issues
Try:
• Testing Outlook on another user account
• Restarting the Mac
• Reinstalling macOS without erasing data
When DIY stops working
You should get on‑site help if:
• Outlook keeps asking for your password every time you open it
• Password prompts return even after re‑entering your details
• macOS reinstall does not fix the issue
• Outlook crashes or freezes during login
• You need your data preserved
These issues usually require:
• Email account and authentication repair
• Outlook profile rebuild
• macOS recovery
• Data‑safe macOS reinstall
• User account repair
• Permissions and system file diagnostics
On‑Site Apple Mac Support – London & South East UK
If Outlook for Mac keeps asking for your password, Keith Thomas provides an often same‑day on‑site support service across:
• Central London
• West, North, South and East London
• Surrey
• Berkshire
• Hampshire
• Wiltshire
Keith Thomas is a Mac Support Specialist in:
• Email login and authentication issues
• Outlook and Microsoft 365 configuration
• macOS configuration repair
• Data‑safe macOS recovery
• macOS reinstall and repair
• New Mac setup and migration
• User account and permissions diagnostics
Book on‑site help in London and the South East UK
If Outlook for Mac keeps asking for your password, Keith Thomas can visit your home or office and get you working again.
Keith Thomas – Apple Mac Support Specialist
Established 2010 – Open 09:30–20:30, 7 Days
Contact Keith Thomas by Telephone: 07800 940756 or by Text to: 07800 940756, or simply complete an online website contact form 24/7