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

Caddy vs Dots

Dots scores 28.3 (F) on agent readiness against Caddy's 16.7 (F), and leads in 3 of 7 scored categories. Caddy leads on reliability, payments & pricing, maintenance & community and transparency & trust. 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 DotsOpenAI · Platform F28.3/100#980 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

  • Reliability, 10 against 3
  • Payments & pricing, 30 against 10
  • Maintenance & community, 55 against 38
  • Transparency & trust, 52 against 31

Watch for

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

Dots F

Best for A ChatGPT Pro or Enterprise user who wants ongoing work tracked across mail, documents, code and Slack with approval before sends.

Ahead on

  • Schema & documentation, 41 against 10
  • Agent ergonomics, 22 against 0
  • Security & auth, 58 against 0

Watch for

Beta. The admin setting is labelled Use dots (Beta), access is rolling out gradually, and Teams access is an invite-only alpha

Score by category

CategoryWeight this runCaddyDotsEdge
Reliability16%20103Caddy +7
Performance10%pendingpendingpendingnot scored in this run
Schema & documentation13%16.21041Dots +31
Agent ergonomics13%16.2022Dots +22
Security & auth14%17.5058Dots +58
Payments & pricing10%12.53010Caddy +20
Task success10%pendingpendingpendingnot scored in this run
Maintenance & community7%8.85538Caddy +17
Transparency & trust7%8.85231Caddy +21
Negative events≤1500
TotalF 16.7/100F 28.3/100

Facts side by side

FactCaddyDots
KindPlatformPlatform
VendorCaddy Technologies Inc.OpenAI
Hosted endpointno (local only)no (local only)
Transports
AuthOAuth or keyOAuth or key
PricingFreePaid
x402nono
LicenceClosed service under Caddy's Terms of Service (Caddy Technologies Inc., last updated 27 April 2026).Proprietary hosted service. The governing terms were not read
Read-only variant documentedyesno
llms.txtyesyes
Last release2026-10-132026-10-09
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

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.

Dots

Actions that affect accounts or share information pass an automatic review, and custom rules can require approval or a hand-off. Dots is a beta on Pro plans from $100 a month, and no status page, terms, privacy policy or way to delete individual saved notes was found in the pages we could read.

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.

Dots

  1. Say what may be sent. Asking a dot to draft replies does not permit sending them, and an action outside a stated scope needs another decision
  2. Stop three things separately. Pause stops the main task only, delegated tasks stop in Activity and recurring tasks in Scheduled, and completed actions are not undone
  3. Connect each thing separately. A messaging channel grants no access to an inbox, an app or a computer
  4. Sign out of websites and disconnect apps yourself when removing access. Revoking dots access or disconnecting an app does not delete information already obtained
  5. Keep the connected computer online with the ChatGPT app open for local work. Only one personal computer can be connected at a time

Questions

Which is better for AI agents, Caddy or Dots?

Dots scores 28.3 (F) on agent readiness against Caddy's 16.7 (F), and leads in 3 of 7 scored categories. Caddy leads on reliability, payments & pricing, maintenance & community and transparency & trust.

Other comparisons with Caddy or Dots

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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