Amazon WorkMail is a cloud-based email and calendaring service by Amazon Web Services (AWS), designed for businesses that want a simple yet secure way to manage emails.
Microsoft Office 365 (now Microsoft 365) is a complete productivity suite that goes beyond email — offering apps like Outlook, Teams, SharePoint, OneDrive, Excel, and Word in one integrated platform.
Over the last few years, many organizations have migrated from Amazon WorkMail to Office 365 to take advantage of its collaboration features, larger storage, better integrations, and enterprise-grade security.
However, the migration process comes with one major concern:
“How do we move all our data without losing a single email, contact, or calendar entry?”
That’s exactly what this guide covers. By the end, you’ll know the most reliable and easiest way to migrate Amazon WorkMail to Office 365 — even if you’re not a technical expert.
Why Migrate from Amazon WorkMail to Office 365?
Switching platforms is never just about changing an email service — it’s about upgrading your business’s productivity tools.
Here are the top reasons companies make the move:
Enhanced Collaboration Tools
- Office 365 offers Microsoft Teams for instant messaging, video calls, and project collaboration.
- SharePoint & OneDrive allow secure document sharing and real-time co-editing.
More Storage & Scalability
- Office 365 typically offers 50GB–100GB mailbox storage per user plus 1TB OneDrive storage, compared to Amazon WorkMail’s 50GB.
- Easily add more users or upgrade plans as your business grows.
Integration with Microsoft Ecosystem
- Seamless sync with Word, Excel, PowerPoint, Planner, and third-party integrations.
- Works across desktop, web, and mobile without compatibility issues.
Advanced Security & Compliance
- Built-in Data Loss Prevention (DLP), encryption, and multi-factor authentication.
- Meets GDPR, HIPAA, and ISO compliance requirements.
Challenges You Might Face During Migration
Migrating from one email platform to another is not just a “drag-and-drop” process. Without planning, you risk:
- Data Loss – Emails, contacts, or calendar events might be missed.
- Email Formatting Issues – HTML emails may lose styles or attachments.
- Downtime – Email service disruptions during migration.
- Manual Complexity – IMAP setup and DNS changes can overwhelm non-technical users.
That’s why choosing the right migration method is critical.
Pre-Migration Checklist
Before you start, ensure these steps are complete:
- Backup Your Amazon WorkMail Data
Export emails, contacts, and calendars as a precaution. - Verify Office 365 Setup
Ensure you have:- Active Office 365 subscription
- Admin privileges for both platforms
- Domain & DNS Preparation
- Add and verify your domain in Office 365 Admin Center
- Prepare to update MX records after migration
- Inform Your Team
- Share migration timelines to avoid interruptions
- Schedule migration during low-activity hours
Migration Methods
There are two primary ways to migrate from Amazon WorkMail to Office 365:
Manual Method – IMAP Migration
The manual approach uses Office 365’s built-in migration feature.
Steps:
- Log in to Office 365 Admin Center.
- Navigate to Setup → Data Migration.
- Select IMAP as the migration type.
- Enter Amazon WorkMail IMAP server details:
- Server:
imap.mail.us-west-2.awsapps.com(Region-specific) - Port: 993
- Encryption: SSL/TLS
- Server:
- Map and migrate user mailboxes.
Pros:
- No extra cost.
- Simple for small mailboxes.
Cons:
- Slow (large mailboxes take hours/days).
- Doesn’t migrate calendars, contacts, or tasks.
- Higher chance of missing or corrupt emails.
Recommended Method – Using a Professional Migration Tool
Specialized migration tools automate and secure the transfer process.
Advantages:
- Migrates emails, contacts, calendars, and attachments in one go.
- Zero downtime — users can continue working during migration.
- Maintains email formatting and folder structure.
- Faster migration with progress tracking.
- No manual server configuration required.
How It Works:
- Connect your Amazon WorkMail account.
- Connect your Office 365 account.
- Choose what data to move (emails, contacts, calendars).
- Apply filters (date range, specific folders).
- Start migration and let the tool handle the rest.
Step-by-Step: Easiest Way to Migrate Without Data Loss
If you want the simplest, safest, and fastest migration, follow these steps with a reliable migration tool:
- Download & Install the tool on your system.
- Login to Amazon WorkMail within the tool using admin credentials.
- Login to Office 365 with admin credentials.
- Select Data Types:
- Emails
- Contacts
- Calendars
- Set Migration Filters:
- Migrate specific date ranges
- Include/exclude folders
- Initiate Migration:
- Monitor live progress
- Pause/resume as needed
- Verify Migration in Office 365 to ensure nothing is missing.
Pro Tip: Always test with a few accounts before doing a company-wide migration.
Post-Migration Steps
Once migration is complete:
- Update MX Records to Office 365 so new emails arrive directly there.
- Check Mailbox Sync — ensure all folders match.
- Test Calendars & Contacts — verify shared calendars work.
- Train Your Team on Office 365 features for faster adoption.
Comparison Table: Amazon WorkMail vs Office 365
| Feature | Amazon WorkMail | Office 365 |
|---|---|---|
| Mailbox Size | 50 GB | 50–100 GB |
| Storage for Files | None | 1 TB OneDrive |
| Collaboration | Basic | Teams, SharePoint, Planner |
| Apps | Email & Calendar | Full Office Suite |
| Security | AWS Security | Microsoft Enterprise Security |
Conclusion
Migrating from Amazon WorkMail to Office 365 is a strategic upgrade for businesses seeking better productivity, scalability, and collaboration tools.
While the manual IMAP method works for small setups, it’s slow and limited.
For zero data loss, faster transfer, and complete migration of all items, a professional migration tool is the best solution.
Final Recommendation: Plan ahead, use a trusted migration tool, and you’ll enjoy a seamless move to Office 365 — without losing a single email.
FAQ – Amazon WorkMail to Office 365 Migration
Yes, with a professional tool, you can keep Amazon WorkMail active until migration is complete, ensuring zero disruption to daily business operations.
Yes, advanced migration tools preserve your folder hierarchy exactly as it was in Amazon WorkMail.
Yes, you can apply filters to migrate emails by date range, specific folders, or even keywords in the subject line.
No, IMAP migration only transfers emails. If you want to migrate calendars, contacts, and tasks, you’ll need a professional migration tool.
The migration time depends on your mailbox size, internet speed, and method used. With a migration tool, most transfers are completed faster compared to the manual IMAP process.
Not necessarily. Many migration tools offer a step-by-step interface suitable for non-technical users. However, large organizations may still prefer IT admin supervision.
Yes, most professional tools support migrating shared mailboxes, distribution lists, and group emails.
Yes, a reliable migration method ensures all attachments, embedded images, and inline files are transferred intact.
First, check your migration report for skipped items. If using a migration tool, you can re-run migration for the missed data only without duplicating existing items.
If migration is done improperly or interrupted, yes. That’s why it’s recommended to use a professional solution with built-in error handling and retry features.
Nathan Matthew is a seasoned tech blogger specializing in email backup and migration solutions. With a keen eye for detail and a passion for simplifying complex tech topics, Nathan helps readers navigate the digital landscape with clarity and confidence. His content is trusted by professionals seeking reliable, easy-to-follow guidance on protecting and managing their email data. When he’s not writing, Nathan is exploring the latest innovations in cloud storage and data security.