Managed IT contracts are hard to compare because everyone lists the same services. These questions separate the quotes.
Every managed IT proposal in this market lists monitoring, support, patching and backup. That makes the quotes look interchangeable and pushes the decision onto price, which is how organisations end up disappointed at a discount.
Ask what the response time actually commits to. 'Four-hour response' usually means someone acknowledges the ticket within four hours, not that anyone attends to it. Ask for the definition in writing, and ask what happens when it is missed.
Ask who attends on site, and from where. A provider covering the whole country from one office is quoting you travel time they have not mentioned.
Ask what happens to your documentation if you leave. Network diagrams, passwords and asset registers built during the engagement should be yours. Some providers treat them as internal, which makes changing supplier far more expensive than it looks.
Ask how licences are held. If Microsoft licences sit under the provider's tenant rather than yours, moving away means a migration rather than a transfer.
Ask when the last restore test was, on any customer. A provider who cannot answer is not running them.
Ask what is explicitly out of scope. The honest answer is a list — project work, hardware, after-hours callouts. A proposal claiming everything is included has moved the exclusions somewhere less visible.
Ask for a reference from a customer who left. Nobody enjoys this question, and the answer tells you more than three happy references will.