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

Caddy vs Town

Town scores 48.7 (D) on agent readiness against Caddy's 16.7 (F), and leads in 6 of 7 scored categories. 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 TownTown.com, Inc. · Platform D48.7/100#834 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.

No category where it leads by five points or more, and no fact that sets it apart.

Watch for

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

Town D

Best for An owner who wants a mail and calendar assistant whose routines other systems can trigger.

Ahead on

  • Reliability, 35 against 10
  • Schema & documentation, 33 against 10
  • Agent ergonomics, 49 against 0
  • Security & auth, 79 against 0
  • Maintenance & community, 60 against 55
  • Transparency & trust, 63 against 52

Also in its favour

  • Free to start without a card

Watch for

The privacy policy describes training with an opt-out and the trust page says training is opt-in.

Score by category

CategoryWeight this runCaddyTownEdge
Reliability16%201035Town +25
Performance10%pendingpendingpendingnot scored in this run
Schema & documentation13%16.21033Town +23
Agent ergonomics13%16.2049Town +49
Security & auth14%17.5079Town +79
Payments & pricing10%12.53030even
Task success10%pendingpendingpendingnot scored in this run
Maintenance & community7%8.85560Town +5
Transparency & trust7%8.85263Town +11
Negative events≤1500
TotalF 16.7/100D 48.7/100

Facts side by side

FactCaddyTown
KindPlatformPlatform
VendorCaddy Technologies Inc.Town.com, Inc.
Hosted endpointno (local only)no (local only)
TransportsHTTP
AuthOAuth or keyOAuth or key
PricingFreeFreemium
x402nono
LicenceClosed service under Caddy's Terms of Service (Caddy Technologies Inc., last updated 27 April 2026).Closed service under Town's Terms of Service (Town.com, Inc., updated 21 July 2026).
Read-only variant documentedyesyes
llms.txtyesno
Last release2026-10-132026-10-10
Terms last updated
Privacy policy last updated
Customer content may train models
Terms restrict automated access
Terms restrict benchmarking
Terms or service can change without notice
Arbitration or class-action waiver

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.

Town

Town is a hosted assistant that works across the owner's mail, calendar and work apps, and other systems can start its routines through per-routine webhooks with rotatable secrets, idempotency keys and documented errors. A caller can't read a run's result. The privacy policy and trust page disagree on whether training is on 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.

Town

  1. Start a Town routine with POST to its webhook URL, Authorization Bearer whsec_ secret, and application/json or text/plain. Expect 202 only.
  2. Send X-Town-Idempotency-Key with a stable event id on every retry so Town doesn't start a second run.
  3. Treat 404 as wrong secret, disabled endpoint or missing endpoint alike, and ask the owner to check Routine Settings rather than retrying.
  4. Send account_email only if the owner allowed the override. It must match a connected account in full and can't widen the routine's scope.
  5. Ask the owner to keep routines that act on webhook input in approval-required mode, as Town's own docs advise.

Questions

Which is better for AI agents, Caddy or Town?

Town scores 48.7 (D) on agent readiness against Caddy's 16.7 (F), and leads in 6 of 7 scored categories.

Other comparisons with Caddy or Town

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.

Town 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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