10/08/2026
We're leaving ConnectWise after 14+ years. Before I migrated a single record, I had to answer one question:
How much of my data is actually coming with me? 🤔
Most people assume all of it. It almost never is.
⚠️ We watched a client get told mid-migration that terabytes of medical records wouldn't make the trip. Pick 1-2 years, leave the rest. Then hire a DBA to move anything else.
🧓 The usual fix? Keep the old system alive for 7+ years on an obsolete OS, paying to secure it so someone can look up a billing question twice a month.
🤖 What I did instead: connected Claude to the old system's API and had it build a searchable, indexed archive of everything. Every ticket. 700,000+ attachments. Invoices, agreements, time entries, all categorized.
💾 It runs as a self-contained app on SQLite. When the OS ages out, copy the folder. No legacy server. No unpatched attack surface.
⏱️ ~50 hours of build time, almost all of it Claude doing the work. My part: 3-4 hours of conversation.
💰 Not $100,000. Not a weekend of my life.
This is part one of a series on what big software migrations really look like, whether it's a PSA, ERP, CRM, or EMR.
👉 Read the full post:
We are moving our professional services automation platform from ConnectWise to Halo. This is the first in a series about that migration, but I want to be clear up front: this is not a how-to for Halo. If you run an ERP, a CRM, an electronic medical record system, or any other heavy business applica...