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

Boski vs Caddy

Boski scores 26.2 (F) on agent readiness against Caddy's 16.7 (F), and leads in 5 of 7 scored categories. Caddy leads on payments & pricing and maintenance & community. Both do proactive personal assistants.

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

BoskiBoski, Inc. · Platform F26.2/100#981 of 1010 CaddyCaddy Technologies Inc. · Platform F16.7/100#996 of 1010

Which one, for what

Boski F

Best for People who want an agent working on personal goals between conversations, and who want ChatGPT or Codex to read their saved preferences.

Ahead on

  • Reliability, 25 against 10
  • Schema & documentation, 15 against 10
  • Agent ergonomics, 13 against 0
  • Security & auth, 45 against 0
  • Transparency & trust, 63 against 52

Watch for

No free plan or trial found.

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 10
  • Maintenance & community, 55 against 23

Watch for

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

Score by category

CategoryWeight this runBoskiCaddyEdge
Reliability16%202510Boski +15
Performance10%pendingpendingpendingnot scored in this run
Schema & documentation13%16.21510Boski +5
Agent ergonomics13%16.2130Boski +13
Security & auth14%17.5450Boski +45
Payments & pricing10%12.51030Caddy +20
Task success10%pendingpendingpendingnot scored in this run
Maintenance & community7%8.82355Caddy +32
Transparency & trust7%8.86352Boski +11
Negative events≤1500
TotalF 26.2/100F 16.7/100

Facts side by side

FactBoskiCaddy
KindPlatformPlatform
VendorBoski, Inc.Caddy Technologies Inc.
Hosted endpointno (local only)no (local only)
Transports
AuthOAuth or keyOAuth or key
PricingPaidFree
x402nono
LicenceClosed service under Boski's Terms of Service (Boski, Inc., a Delaware corporation, effective 20 August 2026).Closed service under Caddy's Terms of Service (Caddy Technologies Inc., last updated 27 April 2026).
Read-only variant documentedyesyes
llms.txtyesyes
Last releasenone2026-10-13
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

Boski

Boski is a hosted personal agent that works on its owner's goals over messaging channels for $5 a week, and its plugin lets ChatGPT and Codex read saved preferences under a read-only OAuth scope. No free option, status page or security contact was found, and the plugin's tool definitions weren't readable.

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.

Before you call either

Boski

  1. Use the Boski plugin only to read the owner's saved preferences and constraints. It can't save changes.
  2. Ask the owner to finish Boski's onboarding interview if the plugin says it's incomplete, then retry.

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.

Questions

Which is better for AI agents, Boski or Caddy?

Boski scores 26.2 (F) on agent readiness against Caddy's 16.7 (F), and leads in 5 of 7 scored categories. Caddy leads on payments & pricing and maintenance & community.

Other comparisons with Boski or Caddy

Disclosure

Boski 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.

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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