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

Caddy vs GAIA

GAIA scores 49.5 (D) on agent readiness against Caddy's 16.7 (F), and leads in 6 of 7 scored categories. Caddy leads on payments & pricing. 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 GAIAThe Experience Company · Platform D49.5/100#816 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

  • Payments & pricing, 30 against 20

Also in its favour

  • No incidents deducted, where GAIA loses 5 points for them

Watch for

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

GAIA D

Best for It suits one person who wants mail triage, meeting briefs, todos and scheduled workflows from one assistant reachable on WhatsApp, Telegram, Slack, Discord or iMessage, and who wants to read the source.

Ahead on

  • Reliability, 67 against 10
  • Schema & documentation, 51 against 10
  • Agent ergonomics, 54 against 0
  • Security & auth, 54 against 0
  • Maintenance & community, 78 against 55
  • Transparency & trust, 60 against 52

Watch for

The default approval mode in the source is always_allow, commented as nothing gated, while the privacy policy and the 26 August release notes say destructive actions wait for approval.

Score by category

CategoryWeight this runCaddyGAIAEdge
Reliability16%201067GAIA +57
Performance10%pendingpendingpendingnot scored in this run
Schema & documentation13%16.21051GAIA +41
Agent ergonomics13%16.2054GAIA +54
Security & auth14%17.5054GAIA +54
Payments & pricing10%12.53020Caddy +10
Task success10%pendingpendingpendingnot scored in this run
Maintenance & community7%8.85578GAIA +23
Transparency & trust7%8.85260GAIA +8
Negative events≤150-5
TotalF 16.7/100D 49.5/100

Facts side by side

FactCaddyGAIA
KindPlatformPlatform
VendorCaddy Technologies Inc.The Experience Company
Hosted endpointno (local only)no (local only)
Transports
AuthOAuth or keyOAuth
PricingFreePaid
x402nono
LicenceClosed service under Caddy's Terms of Service (Caddy Technologies Inc., last updated 27 April 2026).PolyForm-Noncommercial-1.0.0
Read-only variant documentedyesno
llms.txtyesyes
Last release2026-10-132026-09-14
Terms last updated2026-08-14
Privacy policy last updated2026-08-07
Customer content may train modelsnot found in the text
Terms restrict automated accessyes
Terms restrict benchmarkingnot found in the text
Terms or service can change without noticeyes
Arbitration or class-action waiveryes
Popularitynone308 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.

GAIA

GAIA's source is public, so its approval gate, memory store and token handling can be read. Three approval modes and per-tool overrides exist, but the default mode in the source runs every action unasked, which the privacy policy and release notes do not say. Pro costs $30 a month and self-hosting is limited to noncommercial use.

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.

GAIA

  1. Set Settings > Approvals to Always ask or Auto before connecting mail. The default in the source runs every action, including send and delete, without asking.
  2. Expect no public API on the hosted service. The backend turns off its OpenAPI document in production, so reach GAIA through its apps, bots or CLI.
  3. Check the plan before relying on the hosted service. The README and docs describe a Free plan, and the pricing page says GAIA is a paid product.
  4. For self-hosting, prepare Docker, Node.js 20, a WorkOS account and a model key first, and confirm the use is noncommercial under the licence.
  5. Add outside tools as MCP servers by URL on the Integrations page. GAIA asks before adding a server in every approval mode.

Questions

Which is better for AI agents, Caddy or GAIA?

GAIA scores 49.5 (D) on agent readiness against Caddy's 16.7 (F), and leads in 6 of 7 scored categories. Caddy leads on payments & pricing.

Other comparisons with Caddy or GAIA

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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