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Cloud vs self-hosted support desk: the four-question checklist

By the Onsites AI team · Last updated August 28, 2026 · 8-minute read

Cloud-versus-self-hosted used to be an enterprise procurement question. It is not anymore: a forty-person trading firm and a two-hundred-person services company both get asked it now, usually mid-sales-cycle and usually by the customer's compliance person. What still makes teams mis-choose is treating the answer as an identity — "we are a self-hosted company" — instead of what it actually is: four questions with checkable answers. Here is the checklist we use with prospects.

Question 1 · Can customer data leave your network?

If the legally-reviewed answer is no — banking, healthcare, government contractors, defense-adjacent suppliers — self-hosted is not a preference, it is the requirement, and everything else in this checklist is decoration. In self-hosted mode the desk runs on your LAN or your own cloud account, messages never leave your infrastructure, and the vendor has no access to your data at all. If the answer is "yes, mostly," the cloud track's protections (TLS in transit, encryption at rest, seat-based access controls, audit trails) are what most companies actually need, and you should say that plainly instead of paying an ops tax for a compliance scenario you do not have.

Question 2 · Do you budget annually or monthly?

Teams that lurch between procurement cycles prefer a single annual per-seat line item they can defend in one review. Self-hosted is priced for exactly that: $15 per seat per month, billed annually, 10 seats minimum, with installation, updates and support included. Teams that want cost to track headcount prefer the cloud shape: the first three seats are free forever, seat four onward is $15/seat/month prorated daily, and the only meters are opt-in (storage beyond 100 MB at $1/GB/month; AI credits from $10 per pack, prepaid and non-expiring). Neither is more honest — they are honest about different things.

Question 3 · Can you be offline?

Factories, ports, ships and segmented R&D networks have intermittent internet by design, not by accident. A desk that must be reachable when the network is not is a self-hosted deployment: it runs fully disconnected, and AI features simply activate whenever you attach a model — your own API key, a model served inside your network, or an air-gapped endpoint. If nobody in your support operation experiences disconnection as a real scenario, this question is a pass for cloud.

Question 4 · Who maintains it?

Cloud means zero ops: we host, we update, your team answers conversations. Self-hosted usually means your team owns backups and upgrades — on the base product. Onsites self-hosted includes installation, software updates and technical support in the plan, and upgrades ship as two commands (docker compose pull, docker compose up -d) with backward compatibility inside the supported major version. What remains genuinely yours is the one discipline no vendor can absorb: running the included backup script daily, on disks you control.

What each track actually costs

Per-seat, both tracks are the same $15. The differences around the seat decide the invoice. A three-seat team in the cloud pays $0, forever, with no meters unless they opt in — no equivalent self-hosted offer exists or should. A ten-seat cloud team pays for seven seats ($105/month) plus whatever credits and storage they choose to consume. A ten-seat self-hosted team pays $150/month equivalent, billed annually — and supplies its own AI model and storage, so on busy AI usage the self-hosted bill can land lower even as the seat invoice is written larger. The pricing-models blog post compares the shapes; the monthly-cost guide runs worked examples.

The decision, compressed

• Regulated data or air-gap required: self-hosted, full stop. Start with the 60-day pilot.
• Annual procurement culture, ops team exists: self-hosted is the honest fit.
• Everyone else, especially ≤3 seats: cloud free tier, and it is not a trial.
• Unsure: start cloud free this afternoon; the same software moves behind your firewall when a real trigger arrives, not before.

The expensive mistake is treating the track as permanent identity. One codebase feeds both tracks precisely so the choice can be revised when regulation, budgeting or network reality changes. For the deeper mechanics of the self-hosted deployment, read the Docker deployment guide; for licensing and trial terms, the self-hosted page.

Hybrid patterns that work

The tracks also mix. A group with several brands can run each brand in its own workspace and keep all of them free in the cloud, with only the regulated brand self-hosted. A services firm can pilot cloud-free for a quarter and flip to self-hosted the month its largest customer's security review lands — same product, same exports, same widget, new firewall, and the conversations move rather than retooling the team. What does not mix is pretending one track's economics onto the other: cloud meters bill as consumed (seats from the fourth at $15, storage packs at $1/GB, credits prepaid), while self-hosted is a single annual per-seat line whose "meters" are your own disks and your own model. When a compliance officer asks where the messages live, these four questions are the entire answer — and the honest one usually ends at Question 1.