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

Caddy vs Haven

Haven scores 22.2 (F) on agent readiness against Caddy's 16.7 (F), and leads in 3 of 7 scored categories. Caddy leads on schema & documentation and maintenance & community. Both do proactive personal assistants.

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

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

  • Schema & documentation, 10 against 4
  • Maintenance & community, 55 against 35

Watch for

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

Haven F

Best for A consumer assistant for one person who wants to phone, text or email it and have it remember them.

Ahead on

  • Reliability, 35 against 10
  • Agent ergonomics, 6 against 0
  • Security & auth, 13 against 0

Watch for

No approval setting or list of actions that need confirmation was found on the public pages. The terms say it sends emails, SMS and calls following the user's instructions.

Score by category

CategoryWeight this runCaddyHavenEdge
Reliability16%201035Haven +25
Performance10%pendingpendingpendingnot scored in this run
Schema & documentation13%16.2104Caddy +6
Agent ergonomics13%16.206Haven +6
Security & auth14%17.5013Haven +13
Payments & pricing10%12.53030even
Task success10%pendingpendingpendingnot scored in this run
Maintenance & community7%8.85535Caddy +20
Transparency & trust7%8.85251Caddy +1
Negative events≤1500
TotalF 16.7/100F 22.2/100

Facts side by side

FactCaddyHaven
KindPlatformPlatform
VendorCaddy Technologies Inc.Hello Haven, Inc.
Hosted endpointno (local only)no (local only)
TransportsHTTP
AuthOAuth or keyOAuth or key
PricingFreeFree
x402nono
LicenceClosed service under Caddy's Terms of Service (Caddy Technologies Inc., last updated 27 April 2026).Proprietary service under Hello Haven's Terms of Service
Read-only variant documentedyesno
llms.txtyesno
Last release2026-10-132026-09-17
Terms last updated2026-07-24
Privacy policy last updated2026-07-24
Customer content may train modelsnot found in the text
Terms restrict automated accessnot found in the text
Terms restrict benchmarkingnot found in the text
Terms or service can change without noticenot found in the text
Arbitration or class-action waivernot found in the text

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.

Haven

Haven answers by phone call, text, email and app, is free in beta with no card, and publishes a status page with dated incidents. No public page read says which actions need approval, which accounts it connects or how their tokens are kept, and it names no model provider or sub-processor.

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.

Haven

  1. Haven has no documented API or MCP server. An outside agent can reach it only through the owner's channels (call, SMS, email, app).
  2. Do not assume an approval step before Haven sends mail, texts or calls. None is documented on the public pages.
  3. Email Haven sends to other people names Hello Haven as sender and says it was sent on the user's behalf, per the terms.
  4. Chat messages, history, profile context and uploaded files go to third-party AI model providers that the vendor does not name.
  5. Check status.hellohaven.ai before relying on phone or voice. All four published incidents affected those channels.

Questions

Which is better for AI agents, Caddy or Haven?

Haven scores 22.2 (F) on agent readiness against Caddy's 16.7 (F), and leads in 3 of 7 scored categories. Caddy leads on schema & documentation and maintenance & community.

Other comparisons with Caddy or Haven

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.

Machine-readable

For companies

Do agents find, use and choose your tools?

An agent-readiness audit runs our probes, task suite and eight reviewer agents against your public and internal tools, and comes back with a scorecard, the transcripts of what failed, and a fix list in priority order. From $2,500, re-run included. We never take payment to move a rank. We do help companies earn one.