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Head to head · Proactive personal assistants · October 2026 research run

Caddy vs Leon

Leon scores 41 (E) on agent readiness against Caddy's 16.7 (F), and leads in 6 of 7 scored categories. Caddy leads on maintenance & community. Both do proactive personal assistants.

Best AI personal assistants that act for one person · All 834 assistants comparisons

CaddyCaddy Technologies Inc. · Platform F16.7/100#996 of 1010 LeonLouis Grenard (Leon AI) · Agent harness E41/100#938 of 1010

Which one, for what

Caddy F

Best for People who want a free assistant in iMessage or RCS that watches mail, calendars and work tools and asks before acting.

Ahead on

  • Maintenance & community, 55 against 15

Watch for

No API, MCP server or A2A endpoint for an outside agent.

Leon E

Best for A developer who wants a self-hosted assistant with memory, computer use and a local model, and who will read the source.

Ahead on

  • Reliability, 32 against 10
  • Schema & documentation, 33 against 10
  • Agent ergonomics, 57 against 0
  • Security & auth, 34 against 0
  • Payments & pricing, 60 against 30
  • Transparency & trust, 60 against 52

Also in its favour

  • No key needed to call it
  • Free to start without a card
  • Open source

Watch for

No tagged release of the core since 1.0.0-beta.8 on 1 May 2023. The 2.0 Developer Preview is installed by cloning the develop branch

Score by category

CategoryWeight this runCaddyLeonEdge
Reliability16%201032Leon +22
Performance10%pendingpendingpendingnot scored in this run
Schema & documentation13%16.21033Leon +23
Agent ergonomics13%16.2057Leon +57
Security & auth14%17.5034Leon +34
Payments & pricing10%12.53060Leon +30
Task success10%pendingpendingpendingnot scored in this run
Maintenance & community7%8.85515Caddy +40
Transparency & trust7%8.85260Leon +8
Negative events≤1500
TotalF 16.7/100E 41/100

Facts side by side

FactCaddyLeon
KindPlatformAgent harness
VendorCaddy Technologies Inc.Louis Grenard (Leon AI)
Hosted endpointno (local only)no (local only)
Transports
AuthOAuth or keyNone
PricingFreeFree
x402nono
LicenceClosed service under Caddy's Terms of Service (Caddy Technologies Inc., last updated 27 April 2026).MIT
Read-only variant documentedyesno
llms.txtyesno
Last release2026-10-132023-05-01
Terms last updatedno document linked
Privacy policy last updatedno document linked
Customer content may train models
Terms restrict automated access
Terms restrict benchmarking
Terms or service can change without notice
Arbitration or class-action waiver
Popularitynone18k stars

Verdicts

Caddy

Caddy is a free iMessage and RCS assistant in public beta that watches connected mail, calendars and work apps and asks before sending email or changing data. No outside agent can call it, and no status page, changelog or security contact was found, though its iOS app ships every week or two.

Leon

Connected-app credentials are encrypted per profile and the Gmail connection is read-only. The 2.0 Developer Preview has no tagged release, runs tools and a 30-minute proactive pulse with no approval step, listens on every network interface with client authentication off, and sends telemetry by default.

Before you call either

Caddy

  1. Don't plan to call Caddy from another agent. It answers the owner's text messages, Siri and group chats it's added to.
  2. Expect Caddy to ask the owner before it sends email or creates an invite.

Leon

  1. Clone the develop branch for 2.0. npm install --global @leon-ai/cli and docs.getleon.ai install and describe the legacy 1.0 betas
  2. Set client_interface.auth.enabled: true and a LEON_PROFILE_TOKEN before the machine joins a shared network. The server binds 0.0.0.0
  3. Set telemetry_enabled: false and runtime.pulse_enabled: false in the profile config.yml for an unattended or private run
  4. Use availability.tools.allowed to limit tools. Shell, file writes, computer use and browser control are otherwise available to the agent with no approval prompt
  5. Back up LEON_CONNECTIONS_ENCRYPTION_KEY from the profile .env. Without it the stored connections cannot be read

Questions

Which is better for AI agents, Caddy or Leon?

Leon scores 41 (E) on agent readiness against Caddy's 16.7 (F), and leads in 6 of 7 scored categories. Caddy leads on maintenance & community.

Are Caddy and Leon open source?

No open-source release is listed for Caddy. Leon is open source (MIT).

Other comparisons with Caddy or Leon

Disclosure

Caddy competes with LocalGhost, which Anchor Terminal's founder builds. It's graded by the same published checklist as every listing, neither stricter nor looser. Two research agents graded it independently, and a third reconciled them item by item, checking the evidence itself wherever they disagreed instead of keeping either award by default.

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