Replacing Cisco Umbrella: A 2026 Migration Guide for IT Leaders

The short answer

Replacing Cisco Umbrella in 2026 is a side-by-side migration, not a forklift. You deploy the dope.security agent through your MDM in monitor mode, import your existing Umbrella category and domain lists, validate policy on a pilot group, then enforce across the fleet and remove the Umbrella resolver and roaming client. Most teams finish the cutover in days to a few weeks with no downtime. We migrated one Umbrella customer to 2,000 machines in two days.

Why teams are replacing Cisco Umbrella now

Cisco Umbrella grew out of OpenDNS, and DNS filtering is still its center of gravity. You point your network at Cisco's resolvers, and they block lookups to categories and domains you do not want resolved. For a workforce sitting behind an office router, that was a clean fit.

The work moved. Laptops are remote. Traffic is encrypted. Risk lives inside SaaS apps, in AI prompts, and in file uploads. DNS resolution happens before any of that, so it cannot inspect it. To cover the gap, Cisco offers the Umbrella SWG, which backhauls traffic to a Cisco data center for inspection. That narrows the visibility gap and adds a latency one, because every request now takes a detour before it reaches the internet.

The reasons IT leaders give for moving off Umbrella tend to repeat:

• DNS-only filtering misses HTTPS, and the SWG add-on backhauls traffic
• A CISO or auditor asked for on-path TLS inspection and DLP that Umbrella does not natively provide
• ChatGPT, Claude, and Gemini appear in reporting with no tenant-level control
• Remote employees slip past the resolver on personal networks
• One console with SWG, DLP, and CASB looks cheaper than stacking Umbrella tiers, connectors, and roaming clients

If two of these are on your list, a replacement is overdue.

What you are migrating to

dope.security is an agent-based endpoint Secure Web Gateway. The agent sits on the device, decrypts TLS locally, applies your policy, and sends traffic Fly Direct to the internet. There is no resolver to point at and no proxy POP to route through. Dopamine DLP intercepts file uploads and AI prompts. Cloud Application Control restricts SaaS access to corporate tenants. Everything runs through one cloud console, dope.console, built from the ground up rather than assembled through acquisitions.

Migration plan, week by week

This is the playbook we have used for Cisco Umbrella migrations at scale, including the customer who reached 2,000 machines in two days.

Phase	Action with dope.security	Cisco Umbrella state
Week 1, pilot	Push agent via MDM to 20-50 devices in monitor mode	Stays in production, no change
Week 1, policy import	Import category lists and custom domains from Umbrella	Acts as the enforcement layer
Week 2, validate	Compare logs side by side, tune false positives	Still enforcing
Week 2, enforce pilot	Switch pilot group to enforce mode	Bypassed on pilot devices
Week 3, fleet rollout	Push to remaining fleet in waves	Still resolving for unmigrated devices
Week 3, decommission	Validate 100% device coverage in dope.console	Remove resolver from DHCP, retire roaming client, cancel subscription

What you keep, what you gain, what you retire

You keep: your existing MDM, your category lists, your block pages where they matter, your reporting cadence, and your identity provider integration.

You gain: full URL filtering with on-device TLS inspection, Dopamine DLP on uploads and AI prompts, Cloud Application Control for personal versus corporate SaaS tenants, policy that follows the device off-network without a VPN, one console for SWG, DLP, and CASB, and direct-to-internet routing with no backhaul.

You retire: the Umbrella DNS resolver, the SWG proxy POP detour, the roaming client, the SmartProxy and connector setup, and the per-network workarounds you have been doing for users on home Wi-Fi.

What can go wrong, and what does not

Three things teams worry about during a DNS-and-proxy to endpoint migration.

Will users notice? Almost never. The agent works in the background. SSL inspection is local, so there is no certificate warning when it is configured cleanly. Users reach the same sites they always reached, minus the ones your category policy blocks, and often faster than they did through the Umbrella proxy.

Will it break legacy apps? TLS-inspection sensitivity lives in dope.console. You can bypass specific destinations the same way you would tune any proxy, including the pinned-certificate apps that broke under the Umbrella SWG. The bypass list is built to stay short.

Will the agent slow my fleet down? The opposite. The agent runs in under 100 MB of RAM and delivers 4x the performance of legacy proxy SWGs because traffic does not get backhauled to a data center. Greylock Partners moved off Umbrella specifically because the SWG component still routed through Cisco POPs and added latency for a distributed team.

The cost conversation, honestly

Replacing Cisco Umbrella is usually a cost conversation as much as a capability one, so it is worth being straight about it. With Umbrella, the headline DNS price is low, but real coverage means stacking tiers: the SWG add-on for TLS inspection, a CASB for SaaS, the roaming client for off-network devices, and the connectors to tie it together. Each line item is its own renewal and its own configuration. By the time you have parity with what a modern endpoint SWG does out of the box, the bill and the operational load both look very different from the DNS-only sticker price.

dope.security folds URL filtering, on-device TLS inspection, Dopamine DLP, Cloud Application Control, and CASB into one agent and one console. There is no separate roaming client to license and no connector mesh to maintain. For most mid-market teams, consolidating four moving parts into one is where the savings show up, in software spend and in the IT hours you stop spending on integration and edge cases. Fast deployment compounds it: when a rollout takes days instead of a quarter, the breakeven on the switch arrives quickly.

What your users actually experience

A migration is only clean if users barely notice it, and that is the bar we hold. The agent runs in the background. Because SSL inspection is local and configured cleanly, there is no certificate warning and no broken-page surprise. Users reach the same sites they always reached, minus the categories your policy blocks. The one thing they tend to notice is that browsing feels quicker, because traffic is no longer detouring through a Cisco POP before it reaches the internet. For a team that has fielded "the web is slow" tickets since turning on the Umbrella SWG, that change alone is worth the move. Outreach Health saw web-access tickets drop 70% within 90 days of switching to an on-device model.

A note on the Greylock migration

Greylock Partners is a useful reference because the pain was specific. Their DNS-only Umbrella tier missed HTTPS traffic, and turning on the SWG meant backhauling through Cisco data centers, which added latency for a device-first VC team spread across locations. They deployed dope.security through Intune in a phased rollout and went from first proposal to signed contract in 27 days. The IT team's note when it closed: "We are signed. We are excited to be working with you and the team." That is the shape of a clean Umbrella replacement.

Frequently asked questions

How long does it take to replace Cisco Umbrella? Most mid-market IT teams finish the cutover in two to three weeks. Pilot in week one, enforce on the pilot in week two, full rollout and resolver decommission in week three. One Umbrella customer reached 2,000 machines in two days. There is no proxy POP to stand up and no data center work.

Do I have to remove Cisco Umbrella before deploying dope.security? No. Run them in parallel. dope.security in monitor mode shows you exactly what your URL, TLS, and application coverage will look like before you flip enforce on, while Umbrella keeps enforcing.

Will my existing category lists carry over? Yes. dope.console accepts your Umbrella category mappings and custom domain lists. We help with the import on the first call so you are not rebuilding policy by hand.

Does dope.security replace the Umbrella roaming client? Yes. The dope.security agent enforces policy on the device whether it is on corporate Wi-Fi, home Wi-Fi, a hotel network, or a coffee shop. There is no separate roaming client to manage and no VPN required.

Will I lose the DNS-layer protection I have today? No. You gain it and more. The endpoint SWG enforces at the URL, TLS, and application layers, which sit above DNS, so anything Umbrella's resolver caught, the agent catches, plus the encrypted and in-app activity DNS never saw.

Does replacing Umbrella mean replacing my Cisco networking too? No. The dope.security agent runs on the endpoint and is independent of your network gear. You can keep your Cisco switches, routers, and firewalls and simply retire the Umbrella resolver, SWG proxy, and roaming client. The migration touches the security layer, not your network hardware.

What happens to my reporting and logs? dope.console provides URL, TLS, DLP, and application-level reporting in one place, which is deeper than DNS-tier logs because it sees full paths and decrypted content. You can run side by side during the pilot and compare the two log sets directly before you cut over, so there is no reporting gap.

Want a migration plan for your fleet?

Bring the device count and your Cisco Umbrella policy export. We will scope a side-by-side migration in a single call, with no backhaul and no data center stand-up. Start at dope.security.