Step 0: Decide what "cloud" actually means for you

"Move to the cloud" is not a plan. For most Australian SMBs we work with, the practical end-state is two things: Microsoft 365 for email, files and collaboration, and either nothing else or one line-of-business app moved to SaaS. That's it. There is rarely a need to rebuild your on-prem world in Azure VMs — that's a lift-and-shift trap, and it usually costs more than the box you replaced.

Get clear on three answers before you do anything else:

  • Where will email and shared files live? (Almost always: Exchange Online + SharePoint/OneDrive.)
  • Which line-of-business apps stay on-prem, move to SaaS, or get retired?
  • What's the identity story? (Almost always: Entra ID, with SSO into everything else.)

Step 1: Inventory honestly

Before touching anything, write down — on one page — every server, every shared mailbox, every weird mapped drive, every accounting package, every piece of hardware that talks to a domain controller, and every printer that still authenticates via LDAP. Yes, the printer. Especially the printer.

The cheapest mistake in any migration is discovering the existence of a forgotten dependency on the night of cutover.

Step 2: Identity first, always

Set up Entra ID Connect (or its successor, Entra Cloud Sync) and get your existing Active Directory users syncing into the cloud, then enable seamless SSO. This is the unglamorous foundation that makes everything else easy.

Don't try to keep two parallel sets of users in your head. One identity, synced from one source of truth, used everywhere.

If a migration plan doesn't start with identity, it's not a migration plan — it's a list of accidents waiting to happen.

Step 3: Email is the easiest win — do it next

Exchange Online migrations are the most boring, well-trodden path in the entire Microsoft ecosystem. If you're on a hosted Exchange box or even an old on-prem Exchange, run a cutover or staged migration, wait for the MX record to flip, and move on. Use the native Microsoft tooling, not third-party "migration suites" — for small tenants the native path is faster and free.

One nuance worth flagging: pre-stage SPF, DKIM and DMARC records on your DNS the week before, not the morning of. Deliverability problems on day one are 100% avoidable and 100% the thing your CEO will remember.

Step 4: Files — kill the file server

This is where most migrations get bogged down. The temptation is to lift the entire H: drive into one giant SharePoint site. Don't. Take the opportunity to actually re-architect:

  • Personal files → OneDrive (auto-redirect Known Folders for Desktop, Documents, Pictures)
  • Team files → one SharePoint site per team, with sensible permissions
  • Org-wide reference material → a single read-only "Company" SharePoint
  • Archive that hasn't been touched in 3+ years → cold storage, not your live tenant

Use the Migration Manager in the SharePoint admin centre. It's free and it handles permissions, timestamps and large files better than any paid tool we've tried.

Step 5: Decide line-of-business apps one by one

For every remaining on-prem app, pick exactly one of three outcomes:

  • SaaS equivalent exists → move to it. Xero, Halaxy, Cliniko, ServiceM8, simPRO — most Australian verticals are covered now.
  • SaaS doesn't exist but it can live on a single Azure or AWS VM → move it. Right-size the VM aggressively and turn it off at night if usage allows.
  • It's a critical, high-throughput app with no good cloud story → leave it on-prem on a small replacement box and treat that box like a precious thing: backed up, patched, monitored, surrounded by a proper UPS.

Step 6: Switch off the old hardware, then back it up anyway

Once the cutover is done, don't immediately e-waste the old server. Keep it powered down but recoverable for 90 days, then image it to cold storage for another twelve months. Migrations that look successful on day one occasionally reveal a missing share on day forty.

The honest budget

For a typical 10-25 person Australian small business with one on-prem server, an Exchange mailbox plan and a couple of LOB apps, a clean migration is usually 4-8 weeks elapsed, 30-60 hours of consulting time, plus your new M365 licences. Anyone quoting you a five-figure "transformation" for that profile is selling you a deck, not a result.

Want a sanity check?

If you're in the middle of one of these — or staring down the start of one — grab a free 30-minute review. We'll look at your inventory, your licences and your timeline, and tell you the things we'd do differently. No obligation, no slide deck.