AWS WorkMail to Office 365 Migration
Amazon WorkMail → Microsoft 365, with Route 53 DNS flipped by API. WorkMail’s EWS compatibility makes this a clean server-side move — mail, calendars, contacts. The rest of your AWS estate stays exactly as it is. From $15/user.
BitTitan Certified · Zero Data Loss Record · DNS Handled
Every mailbox. Every folder. Verified.
What staying actually costs.
No Teams-class collaboration, thin client support — WorkMail leans on Outlook anyway. You’re running Microsoft’s client against Amazon’s server and getting the best of neither.
WorkMail’s per-mailbox fee plus the Office licenses you’re buying separately exceeds Microsoft 365 Business Basic — which includes the collaboration stack.
WorkMail journaling and retention data needs explicit export handling before decommission — we script it as part of the exit.
Route 53 cutover is API-driven — the fastest MX flip in the business. No portal clicking, no propagation guessing.
Everything handled. Nothing assumed.
Server-side EWS migration
WorkMail exposes EWS — mail, calendars, and contacts migrate server-side with good fidelity, no per-user client work.
WorkMail org enumeration
Users, groups, aliases, and resources enumerated from the WorkMail organization via API and recreated in Microsoft 365.
Route 53 API cutover
MX, SPF, DKIM, and Autodiscover records updated in Route 53 by API at cutover — scripted, instant, reversible.
SES flow re-pointing
SES inbound rules and app mail flows that fed WorkMail get re-pointed to Microsoft 365 connectors so application mail keeps flowing.
AWS estate untouched
Only mail moves. EC2, S3, SES outbound, IAM — everything else in the account stays exactly as it is.
Compliance export handling
WorkMail journaling/retention data exported and preserved before the organization is deleted — a compliance step most DIY exits miss.
Assess. Plan. Migrate. Cutover.
Assess
1-2 days · Source audit, mailbox inventory, domain list. Fixed per-user quote in 24-48 hours.
Plan
1-2 days · Microsoft 365 tenant provisioned, domains verified, MFA + security baseline deployed.
Migrate
Background · Server-side pre-stage sync runs invisibly. Users keep working on the old system until cutover.
Cutover
2-4 hrs off-hours · MX/SPF/DKIM flip, final delta sync, Autodiscover repoint. 30 days hypercare.
The engineers on your project.
No outsourced ticket triage. The same three engineers handle source assessment, tenant provisioning, cutover night, and post-migration support on every Amazon WorkMail engagement.
Sreenivasa Reddy
Founder & Principal Migration Engineer
MCSE Messaging · 25 yrs · 500+ migrations led
Owns the discovery call and migration architecture: source assessment, licensing right-size, and the compliance/security mapping that decides which M365 SKU mix you actually need.
Roshan Pujari
Senior Migration Engineer · Source Systems Lead
Microsoft Certified · M365 Administrator
Runs source-side assessment and extraction: credentials, throttling strategy, batch design, and the pre-stage sync that makes cutover weekends boring.
Bhargav
Senior Migration Engineer · Mail Flow + Cutover
Microsoft Certified · Exchange + M365 Messaging
MX/SPF/DKIM/DMARC cutover and Autodiscover repoint. Owns the 2-4 hour cutover window plus post-cutover Outlook profile and mobile device resync.
The Amazon WorkMail-specific realities.
Generic migration guides skip these. They are the operational details that decide whether your cutover weekend is boring — which is the goal.
WorkMail journaling/retention exports need handling before decommission if you have compliance requirements — we script the export
Route 53 stays in AWS — only mail records change; your infrastructure, SES outbound, and hosted zones are untouched
WorkMail-integrated apps (SES inbound rules) must be re-pointed to M365 connectors, or application mail silently dies at cutover
Frequently Asked Questions
Why do companies leave AWS WorkMail for Office 365?+
Does the rest of our AWS infrastructure change?+
How fast is an AWS WorkMail migration?+
What is the downtime during a Amazon WorkMail to Microsoft 365 migration?+
Is there any risk of data loss?+
What does the migration include for $15/user?+
WorkMail was an experiment. End it.
$15/user flat. Pre-staged sync, off-hours cutover, DNS handled, 30-day hypercare. Zero data loss record across 1.4M users.
Microsoft Solutions Partner · BitTitan certified · Fixed-fee · 500+ migrations
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