Should I worry about a business's compliance history with its regulator, even if unrelated to my deal?

Generally yes, worth checking, even for issues that seem unrelated to why you're buying. Many Ontario businesses operate under sector-specific licences or regulatory oversight — food service, personal services, trades, health-related businesses, and others — and a pattern of compliance problems, even minor or seemingly unconnected ones, can indicate weak operational management more broadly, not just a risk in that one narrow area.

There's also a practical closing risk: some licences and permits are personal to the current licensee and don't automatically transfer to a new owner, and a regulator with an open compliance concern may be slower to approve a transfer, impose conditions, or scrutinize the new owner more closely than they would an operator with a clean record. This can affect your timeline and, in some cases, your ability to operate the business at all right after closing.

Ask specifically about any regulatory inspections, warnings, or enforcement actions in recent years, not just ones tied to what you're worried about, and confirm what's required to transfer or re-obtain any necessary licences in your own name. A Treadstone business lawyer can help identify what regulatory approvals your specific deal will need.