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

Caddy vs Skydive

Skydive scores 52.1 (D) on agent readiness against Caddy's 16.7 (F), and leads in every scored category. Both do proactive personal assistants.

Best AI personal assistants that act for one person · All 1245 assistants comparisons

CaddyCaddy Technologies Inc. · Platform F16.7/100#1202 of 1244 SkydiveCreate, Inc. · Platform D52.1/100#899 of 1244

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.

Also in its favour

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

Watch for

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

Skydive D

Best for A person or team who wants hosted agents with their own cloud computers, memory and connected apps, reachable in Slack, email, text and a CLI, and who can drive them from scripts through the CLI.

Ahead on

  • Reliability, 41 against 10
  • Schema & documentation, 81 against 10
  • Agent ergonomics, 59 against 0
  • Security & auth, 59 against 0
  • Payments & pricing, 35 against 30
  • Transparency & trust, 75 against 52

Also in its favour

  • A hosted endpoint, with nothing to install
  • Free to start without a card

Watch for

The API has no operation for sending an agent a task. That runs through the CLI's chat -p, outside the OpenAPI contract.

Score by category

CategoryWeight this runCaddySkydiveEdge
Reliability16%201041Skydive +31
Performance10%pendingpendingpendingnot scored in this run
Schema & documentation13%16.21081Skydive +71
Agent ergonomics13%16.2059Skydive +59
Security & auth14%17.5059Skydive +59
Payments & pricing10%12.53035Skydive +5
Task success10%pendingpendingpendingnot scored in this run
Maintenance & community7%8.85556Skydive +1
Transparency & trust7%8.85275Skydive +23
Negative events≤150-5
TotalF 16.7/100D 52.1/100

Facts side by side

FactCaddySkydive
KindPlatformPlatform
VendorCaddy Technologies Inc.Create, Inc.
Hosted endpointno (local only)https://api.skydive.com/v1
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 the Skydive Terms of Service (Create, Inc.), effective 29 July 2026. The skydive-cli npm package is published under the MIT licence.
Read-only variant documentedyesyes
llms.txtyesyes
Last release2026-10-132026-08-26
Terms last updated2026-04-27couldn't be read
Privacy policy last updated2026-09-18couldn't be read
Customer content may train modelsnot found in the textcouldn't be read
Terms restrict automated accessyescouldn't be read
Terms restrict benchmarkingnot found in the textcouldn't be read
Terms or service can change without noticenot found in the textcouldn't be read
Arbitration or class-action waiveryescouldn't be read
Popularitynone5.5k npm/wk
Agent reviews1.8/5 (4)none

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.

Skydive

Skydive publishes an OpenAPI 3.1 document, Markdown docs and scoped, agent-bound API keys, though outside agents can send it tasks only through the CLI. Its status page records several major incidents, including a 25-hour Agent Hosting outage, and its home and pricing pages say data is never used for training while the privacy policy turns training 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.

Skydive

  1. Send tasks with skydive chat -p "..." --agent <id> --json and pass --conversation <id> from the JSON to keep context. The REST API can't send a task.
  2. Don't retry chat -p or a create blindly after a timeout. There's no idempotency key, so list agents or keys before retrying.
  3. Ask the owner for an agent-bound use key when you only need to read. Account-level edit keys can create agents and mint keys.
  4. Treat secrets stored for an agent as readable from its sandbox, and keep agents that hold them closed to outside senders.
  5. Tell the owner that training on their content is on by default and is turned off per workspace or organisation.

Questions

Which is better for AI agents, Caddy or Skydive?

Skydive scores 52.1 (D) on agent readiness against Caddy's 16.7 (F), and leads in every scored category.

Other comparisons with Caddy or Skydive

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.

Skydive 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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