sync: auto-sync from GURU-5070 at 2026-06-25 19:18:08

Author: Mike Swanson
Machine: GURU-5070
Timestamp: 2026-06-25 19:18:08

projects/msp-tools/runbooks/google-workspace-to-m365-migration.md

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+# Runbook: Google Workspace (Gmail) → Microsoft 365 mail migration
+
+Reusable ACG process for moving a client's mail (and optionally calendar/contacts) from Google
+Workspace to Exchange Online. Covers method selection, prerequisites, the native Microsoft path
+end-to-end, the MX cutover, and gotchas. Author: 2026-06-25 (first written while scoping Birth
+Biologic). Status: working draft — refine after the first real run.
+
+---
+
+## 1. Pick the method
+
+| Method | Moves | Cost | When to use |
+|---|---|---|---|
+| **MS native "Migration from Google Workspace"** (EAC) | mail + calendar + contacts, with incremental/delta sync | **Free** | **Default.** Need Google super-admin to set up a service account + domain-wide delegation on the source tenant. |
+| **IMAP migration** (EAC) | **mail only** | Free | Fallback when you can't get domain-wide delegation. Gmail labels→folders get messy; no calendar/contacts. |
+| **BitTitan MigrationWiz** (3rd-party) | mail + cal + contacts + Drive, coexistence, best throttling/reporting | ~$12–15/mailbox | Larger/complex jobs, strict cutover windows, or to make this a repeatable productized service. **ACG has no BitTitan account yet.** |
+| **Takeout MBOX / Gmail→PST → 365 PST Import** | mail only, one-shot | Free | Last resort / archival only. Manual, per-mailbox, no delta, fidelity loss. Avoid for live cutovers. |
+
+Default to the **MS native** path below.
+
+---
+
+## 2. Prerequisites (all methods)
+
+- **Google super-admin** on the SOURCE Workspace tenant (for the SA + domain-wide delegation, or an app password for IMAP). **This is the #1 gate — confirm it before quoting timelines.**
+- **M365 target tenant** with the client's domain **added and verified** (do NOT cut MX yet), and **licensed mailboxes provisioned** for every user being migrated.
+- **DNS control** for the MX/autodiscover/SPF/DKIM cutover — know the registrar AND the DNS host (often different). Get edit access ahead of time.
+- **Inventory** (from the Google Admin console): user list + mailbox sizes, shared mailboxes / delegated mailboxes, groups/distribution lists, aliases, calendars/resources, and who's actually active.
+- **Vault** the source Google admin creds / SA per the ACG pattern (see §6).
+
+---
+
+## 3. ACG reusable asset — the Google domain-wide-delegation SA
+
+ACG already has a Google service account for Workspace access:
+`msp-tools/acg-msp-access-google-workspace.sops.yaml` →
+`acg-msp-access@acg-msp-access.iam.gserviceaccount.com` (GCP project `acg-msp-access`).
+- Currently scoped for the **security-assessment** read path (`gmail.readonly`, `drive.readonly`,
+  `admin.directory.user`, `reports.audit`, etc.) and **onboarded only to lonestarelectrical.net**.
+- For a **migration** you can reuse this SA (or create a per-job one) — but the migration needs the
+  **migration scopes** added to the SA's **domain-wide delegation in the SOURCE client's Google Admin
+  console**, not just ACG's project. Microsoft specifies the exact scopes (see §4 step 1).
+- Reusing the same SA across clients is fine; each source tenant separately authorizes the SA's
+  `client_id` in *their* Admin console. Keep the key in the vault; rotate per the entry's notes.
+
+---
+
+## 4. MS native migration — end to end
+
+**Step 1 — Source (Google) prep**
+1. In **GCP** (project `acg-msp-access` or a new one): ensure the service account exists and a JSON key is in the vault. Enable APIs: **Gmail, Google Calendar, Google People (Contacts), Admin SDK (Directory)**.
+2. In the SOURCE **Google Admin console** → Security → API controls → **Domain-wide delegation** → add the SA **Client ID** with the Microsoft-required OAuth scopes (Gmail/Calendar/Contacts/Directory — copy the exact scope list from the EAC migration wizard so they match).
+3. Confirm a Google super-admin mailbox exists for the migration to impersonate.
+
+**Step 2 — Target (M365) prep**
+1. Add + **verify the client domain** in M365 (TXT). Do **not** change MX yet.
+2. **Provision + license** every target mailbox (match Google addresses). Create any missing ones.
+3. (Optional) pre-create shared mailboxes / distribution groups to mirror Google.
+
+**Step 3 — Create + run the migration batch**
+1. EAC → **Migration → Add migration batch → "Migration from Google Workspace."**
+2. Provide the **SA JSON key** + the super-admin to impersonate; upload a **CSV** of mailboxes
+   (`EmailAddress` of each source/target — they match on the verified domain).
+3. Start the batch → **initial sync**, then it keeps doing **incremental/delta** passes. Leave it
+   running (days for large mailboxes). Monitor the batch report for skipped items.
+
+**Step 4 — Validate**
+- Spot-check a few migrated mailboxes (mail counts, folders, calendar, contacts). Resolve large
+  skipped-item counts before cutover.
+
+**Step 5 — MX cutover (the go-live)**
+1. **Lower TTL** on MX (and autodiscover) at the DNS host 24–48h ahead.
+2. Flip **MX** → M365 (`<tenant>-com.mail.protection.outlook.com`), update **SPF**
+   (`include:spf.protection.outlook.com`), republish **DKIM** (enable in Defender, add the 2 CNAMEs),
+   set **autodiscover** CNAME → `autodiscover.outlook.com`, review **DMARC**.
+3. Run a final **incremental** sync after cutover to catch mail delivered to Google during propagation.
+4. **Complete/finalize** the batch.
+
+**Step 6 — Decommission**
+- After a validation window: reconfigure clients (Outlook/mobile to M365), remove Google licenses,
+  remove the SA's domain-wide delegation from the client's Admin console, cancel Workspace.
+
+---
+
+## 5. Gotchas
+
+- **Labels → folders:** Gmail labels become folders; a message with multiple labels can duplicate. The
+  native tool handles the primary label; expect minor structure differences.
+- **Shared / delegated mailboxes, groups, aliases, calendars/resources** don't all come across as
+  "mailboxes" — inventory and recreate them in M365 deliberately.
+- **Throttling:** Google + EXO both throttle; large tenants take days. Don't promise same-day.
+- **SPF/DKIM/DMARC:** must be updated at cutover or outbound mail fails auth / inbound double-delivers.
+- **Don't cut MX early** — mail in flight to Google after an early MX flip is missed until the final delta.
+- **Calendar/contacts** only migrate via the native tool or BitTitan, NOT via IMAP.
+- **Retention/litigation hold:** if the client needs Google data retained, export before decommission.
+
+## 6. Credentials & vault
+
+- Source Google admin / SA: vault under `clients/<slug>/google-workspace.sops.yaml` (see
+  `clients/lonestar-electrical/google-workspace.sops.yaml` for the shape) or reuse
+  `msp-tools/acg-msp-access-google-workspace.sops.yaml` (note which clients it's delegated to).
+- **Never echo the SA JSON / private key in chat** — read named fields with `vault.sh get-field`,
+  not a regex over the whole blob (a line-redaction missed a `private_key` once — errorlog 2026-06-25).
+- Target M365: the client's tenant-admin path (CIPP / remediation-tool / GA).
+
+## 7. Make it a service (future)
+
+If Google→365 jobs recur, decide: standardize on the **native** path (free, this runbook) vs. buy
+**BitTitan** (productized, per-mailbox, coexistence). Promote this runbook to a wiki pattern via
+`/wiki-compile` once proven on the first real migration.