What We'll Do
I will schedule a remote session with Mike Joly to walk through every part of the current environment from end to end. Using TeamViewer, we will connect to each server and workstation, document what is running, and record the details that matter for a clean migration.
This is the "measure twice, cut once" phase. It validates our understanding of your infrastructure and ensures there are no surprises once migration work begins. No changes will be made to the production environment during this phase.
Discovery Checklist
- Schedule TeamViewer session with Mike Joly
- Remote into each server: verify OS versions, disk usage, and running services
- Walk file server shares: inventory folders, sizes, permissions, and last-modified dates
- Interview Karen regarding QuickBooks workflow (features used, multi-user needs, reporting)
- Count active mailboxes and distribution lists in Exchange
- Document printer IP addresses at both offices
- Verify ISP speeds at both office locations (speedtest)
- Document any line-of-business applications not in our records
- Confirm active user headcount with Mike
- Document PC ownership: which users own their PCs vs. company-owned devices
- Assess mobile device usage: who accesses email on phones, which apps
- Identify shared PC situations (reception, conference room, etc.)
- Discuss PC budget willingness: must-replace only vs. optional upgrades
- Present finalized migration proposal to Mike for approval
- Confirm who holds Network Solutions DNS credentials and verify login works
- Pull current TTL values on all DNS records — lower to 300s at least 48hrs before cutover
- Export current SPF record in full — verify whether 72.70.41.163 is listed as authorized sender
- Check Exchange 2013 SSL certificate: valid, trusted, not self-signed?
- Test autodiscover from external network (not from inside the office)
- Run
Test-MigrationServerAvailabilityfrom Exchange Online admin center during discovery - Pull SonicWall firewall rules — document any rules touching port 443 on 72.70.41.163
- Inventory shared mailboxes and document all delegate permissions (Send As, Full Access)
- Check whether Exchange 2013 public folders exist and are in use
- Check all mailbox sizes — flag any over 10GB for pre-migration cleanup
- Inventory mobile devices with email configured (iOS/Android, native mail vs Outlook app)
- Confirm LOB apps beyond QuickBooks: Dotloop, DocuSign, ShowingTime, MLS tools, transaction management, CRM — anything that authenticates against AD or sends mail through Exchange
- Open \\bwfile\address and document exactly what is in it — shared contacts, address books, or data files
- Confirm Hyper-V VM inventory on BWHOST/BOARDWALK-2013: which VMs are running, which roles each holds, confirm no VM running on host before host is powered off
Open Questions
These are the items we need to resolve during the discovery session. Each question directly affects scope, cost, or timeline.
| # | Question | Why It Matters |
|---|---|---|
| 1 | QuickBooks version and daily features Karen uses | Determines whether QuickBooks Online is a viable replacement or if we need a hosted Desktop solution |
| 2 | Exact active user headcount | Determines license count and monthly cost |
| 3 | ISP speeds at both offices | Cloud-only requires a minimum of 50 Mbps download; slow connections would degrade the experience |
| 4 | Workstation inventory (desktops vs. laptops per user) | Determines hardware order quantities and form factors |
| 5 | Any line-of-business apps besides QuickBooks (MLS tools, CRM, transaction management) | May require additional cloud solutions or hosted environments |
| 6 | Which file shares are active vs. archive | Reduces migration scope and speeds up the file transfer |
| 7 | Printer models, IP addresses, and locations | Needed for direct IP printing setup; no compatibility concerns with this approach |
| 8 | Active mailboxes, distribution lists, and shared mailboxes | Determines Exchange migration scope and licensing needs |
| 9 | Wakefield office: still active? How many staff? | Determines if the site-to-site VPN is still needed or can be retired |
| 10 | Company and personal mobile devices used for work | Determines MAM policy scope and mobile setup guide distribution |
| 11 | Who holds Network Solutions credentials? | DNS access required for cutover — locked out at 11pm Saturday is a project-stopper |
| 12 | SSL certificate on Exchange: self-signed or CA-issued? Expiry date? | Migration endpoint creation fails on self-signed or expired certs |
| 13 | Is autodiscover working from outside the network? | Migration tool depends on autodiscover — silent failures if broken |
| 14 | What is in \\bwfile\address? | May contain shared Outlook contacts or address books that disappear post-migration |
| 15 | Are Exchange 2013 public folders in use? | Not migrated by cutover — requires separate process |
| 16 | Does anyone have delegate access (Send As / Full Access) on shared mailboxes? | Delegate permissions must be manually re-applied in Exchange Online |
| 17 | How many staff have email on mobile? Native mail app or Outlook? | ActiveSync configs break post-cutover — need reconfiguration plan |
| 18 | Any LOB apps that authenticate against AD or send via Exchange? | Break when AD and Exchange go offline — needs separate remediation |
| 19 | Any mailboxes over 10GB? | Large mailboxes throttle and stall the cutover migration batch |
Deliverable
At the end of Phase 0, we will have a finalized migration scope, an approved budget, and new PC hardware on order. This gives us a clear, agreed-upon plan before any technical work begins.
Estimated Timeline
One week. No changes will be made to the production environment during this phase. Everything in Phase 0 is observation, documentation, and planning.