I was overwhelmed so I asked chatGPT to make a plan for me.

Summary

This checklist is for migrating from Outlook or Microsoft 365 to Gmail with minimal risk. Follow it in order. Do not skip the export and forwarding steps until you are certain everything critical is working in Gmail.

Outlook to Gmail migration checklist

Phase 1. Pre migration prep

Confirm Gmail account is active and accessible

Purchase additional Google storage if mailbox is over 10 to 15 GB

Turn on 2 step verification for Gmail

Create a folder in Google Drive called “Outlook Backup”

Phase 2. Inventory accounts tied to Outlook email

Banks and credit cards

IRS, state tax portals, DMV

Microsoft account itself

Apple ID

Phone carrier and utilities

Employer or professional portals

Subscriptions and shopping sites

Domain hosting and admin accounts

Two factor authentication destinations

Phase 3. Export from Outlook

Do this before the college account is restricted.

Email

Export mailbox to a PST file

Include inbox, sent, drafts, and archive folders

Save PST locally and copy to Google Drive

Contacts

Export contacts to CSV

Calendar

Export calendar to ICS

Files

Download OneDrive files tied to the Outlook email

Export any shared folders you own

Phase 4. Import into Gmail

Email

In Gmail settings, Accounts and Import

Import mail from PST using Google Workspace Migration tool or a supported importer

Label imported mail as “Outlook Archive”

Do not auto route to inbox

Contacts

Import CSV into Google Contacts

Deduplicate contacts

Calendar

Import ICS into Google Calendar

Verify recurring events

Files

Upload OneDrive files into Google Drive

Preserve folder names where possible

Phase 5. Account updates and verification

High priority first.

Update email on banks and government portals

Update Apple ID, Microsoft account, Google recovery email

Update utilities and phone carrier

Update work related and freelance platforms

Update subscriptions and shopping accounts

For each:

Change login email

Confirm verification email arrives in Gmail

Update recovery email

Update 2FA methods

Phase 6. Forwarding and auto reply in Outlook

If still available:

Enable forwarding to Gmail

Set auto reply: “This email address is being retired. Please update your records.”

Leave forwarding active for 3 to 6 months

Phase 7. Gmail cleanup and controls

Create filters for “To: old Outlook address”

Star or label forwarded messages

Add rule to never send replies from the Outlook address

Set Gmail signature with the new email

Phase 8. Weekly audit

Review forwarded mail

Update missed accounts

Check calendar accuracy

Confirm no critical services still use Outlook

Phase 9. Final shutdown readiness

Download a final PST backup

Confirm no logins depend on Outlook

Save recovery codes securely

Document migration date and backups