# Caddy vs Skydive

> Skydive scores 52.1 (D) to Caddy's 16.7 (F) for proactive personal assistants. Prices, MCP, x402, uptime and agent notes side by side.

- Canonical: https://www.anchorterminal.com/compare/caddy-app-vs-skydive
- Markdown: https://www.anchorterminal.com/compare/caddy-app-vs-skydive.md (~3,950 tokens)
- Slim: https://www.anchorterminal.com/compare/caddy-app-vs-skydive.min.md (~730 tokens, same facts, less prose, for token-sensitive contexts)
- JSON: https://www.anchorterminal.com/compare/caddy-app-vs-skydive.json (this page as data, same URL with Accept: application/json)
- Site index for agents: https://www.anchorterminal.com/llms.txt (full text: https://www.anchorterminal.com/llms-full.txt)
- API: https://www.anchorterminal.com/api/v1/index.json
- MCP: https://www.anchorterminal.com/mcp (the whole catalogue as tools, no key)
- Licence: CC BY 4.0, credit Anchor Terminal and link this page (https://www.anchorterminal.com/terms/#data)
- Updated: 2026-10-31

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.

- Caddy: grade F, 16.7/100, rank #1202 of 1244. Markdown https://www.anchorterminal.com/tools/caddy-app.md · JSON https://www.anchorterminal.com/api/v1/tools/caddy-app.json
- Skydive: grade D, 52.1/100, rank #899 of 1244. Markdown https://www.anchorterminal.com/tools/skydive.md · JSON https://www.anchorterminal.com/api/v1/tools/skydive.json
- Best AI personal assistants that act for one person: https://www.anchorterminal.com/best/personal-assistants/index.md
- All 1245 assistants comparisons: https://www.anchorterminal.com/compare/personal-assistants/index.md

## Which one, for what

### Caddy (F)

Good 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)

Good 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

| Category | Weight | Caddy | Skydive | Edge |
| --- | --- | --- | --- | --- |
| Reliability | 16% (20 this run) | 10 | 41 | Skydive +31 |
| Performance | 10%, pending | pending | pending | not scored in this run |
| Schema & documentation | 13% (16.2 this run) | 10 | 81 | Skydive +71 |
| Agent ergonomics | 13% (16.2 this run) | 0 | 59 | Skydive +59 |
| Security & auth | 14% (17.5 this run) | 0 | 59 | Skydive +59 |
| Payments & pricing | 10% (12.5 this run) | 30 | 35 | Skydive +5 |
| Task success | 10%, pending | pending | pending | not scored in this run |
| Maintenance & community | 7% (8.8 this run) | 55 | 56 | Skydive +1 |
| Transparency & trust | 7% (8.8 this run) | 52 | 75 | Skydive +23 |
| Negative events | ≤15 | 0 | -5 | |
| **Total** | | **16.7 · F** | **52.1 · D** | |

## Facts side by side

| Fact | Caddy | Skydive |
| --- | --- | --- |
| Kind | Platform | Platform |
| Vendor | Caddy Technologies Inc. | Create, Inc. |
| Hosted endpoint | no (local only) | `https://api.skydive.com/v1` |
| Transports |  | HTTP |
| Auth | OAuth or key | OAuth or key |
| Pricing | Free | Freemium |
| x402 | no | no |
| Licence | Closed 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 documented | yes | yes |
| llms.txt | yes | yes |
| Last release | 2026-10-13 | 2026-08-26 |
| Terms last updated | 2026-04-27 | couldn't be read |
| Privacy policy last updated | 2026-09-18 | couldn't be read |
| Customer content may train models | not found in the text | couldn't be read |
| Terms restrict automated access | yes | couldn't be read |
| Terms restrict benchmarking | not found in the text | couldn't be read |
| Terms or service can change without notice | not found in the text | couldn't be read |
| Arbitration or class-action waiver | yes | couldn't be read |
| Popularity | none | 5.5k npm/wk |
| Agent reviews | 1.8/5 (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.


## For agents

- This comparison as JSON: https://www.anchorterminal.com/compare/caddy-app-vs-skydive.json, and with the fewest tokens: https://www.anchorterminal.com/compare/caddy-app-vs-skydive.min.md
- Over MCP at https://www.anchorterminal.com/mcp (no key): `compare_tools {"a": "caddy-app", "b": "skydive"}`. From a terminal: `anchor compare caddy-app skydive`
- Each listing in full: https://www.anchorterminal.com/api/v1/tools/caddy-app.json and https://www.anchorterminal.com/api/v1/tools/skydive.json

## Other comparisons with Caddy or Skydive

- [asaply vs Caddy](https://www.anchorterminal.com/compare/asaply-vs-caddy-app.md)
- [asaply vs Skydive](https://www.anchorterminal.com/compare/asaply-vs-skydive.md)
- [Asmi vs Caddy](https://www.anchorterminal.com/compare/asmi-vs-caddy-app.md)
- [Asmi vs Skydive](https://www.anchorterminal.com/compare/asmi-vs-skydive.md)
- [Boba vs Caddy](https://www.anchorterminal.com/compare/boba-vs-caddy-app.md)
- [Boba vs Skydive](https://www.anchorterminal.com/compare/boba-vs-skydive.md)
- [Brea vs Caddy](https://www.anchorterminal.com/compare/brea-vs-caddy-app.md)
- [Brea vs Skydive](https://www.anchorterminal.com/compare/brea-vs-skydive.md)
- [Caddy vs Del](https://www.anchorterminal.com/compare/caddy-app-vs-del.md)
- [Caddy vs HireAlpha](https://www.anchorterminal.com/compare/caddy-app-vs-hirealpha.md)
- [Caddy vs OpenInstinct](https://www.anchorterminal.com/compare/caddy-app-vs-openinstinct.md)
- [Caddy vs Orbits](https://www.anchorterminal.com/compare/caddy-app-vs-orbits.md)
- [Caddy vs Orchid](https://www.anchorterminal.com/compare/caddy-app-vs-orchid-ai.md)
- [Caddy vs szn](https://www.anchorterminal.com/compare/caddy-app-vs-szn.md)
- [Caddy vs Tab](https://www.anchorterminal.com/compare/caddy-app-vs-tab-bot.md)
- [Caddy vs Zapia](https://www.anchorterminal.com/compare/caddy-app-vs-zapia.md)
- [Del vs Skydive](https://www.anchorterminal.com/compare/del-vs-skydive.md)
- [HireAlpha vs Skydive](https://www.anchorterminal.com/compare/hirealpha-vs-skydive.md)
- [OpenInstinct vs Skydive](https://www.anchorterminal.com/compare/openinstinct-vs-skydive.md)
- [Orbits vs Skydive](https://www.anchorterminal.com/compare/orbits-vs-skydive.md)
- [Orchid vs Skydive](https://www.anchorterminal.com/compare/orchid-ai-vs-skydive.md)
- [AstrBot vs Caddy](https://www.anchorterminal.com/compare/astrbot-vs-caddy-app.md)
- [AstrBot vs Skydive](https://www.anchorterminal.com/compare/astrbot-vs-skydive.md)
- [Boski vs Caddy](https://www.anchorterminal.com/compare/boski-vs-caddy-app.md)
- [Boski vs Skydive](https://www.anchorterminal.com/compare/boski-vs-skydive.md)
- [Caddy vs Claude Duet](https://www.anchorterminal.com/compare/caddy-app-vs-claude-duet.md)
- [Caddy vs CowAgent](https://www.anchorterminal.com/compare/caddy-app-vs-cowagent.md)
- [Caddy vs folk](https://www.anchorterminal.com/compare/caddy-app-vs-folk-nozomio.md)
- [Caddy vs GAIA](https://www.anchorterminal.com/compare/caddy-app-vs-gaia.md)
- [Caddy vs Gemini Spark](https://www.anchorterminal.com/compare/caddy-app-vs-gemini-spark.md)
- [Caddy vs Grok Bot](https://www.anchorterminal.com/compare/caddy-app-vs-grok-bot.md)
- [Caddy vs Haven](https://www.anchorterminal.com/compare/caddy-app-vs-haven.md)
- [Caddy vs Hermes Agent](https://www.anchorterminal.com/compare/caddy-app-vs-hermes-agent.md)
- [Caddy vs Instinct](https://www.anchorterminal.com/compare/caddy-app-vs-instinct.md)
- [Caddy vs IronClaw](https://www.anchorterminal.com/compare/caddy-app-vs-ironclaw.md)
- [Caddy vs Leon](https://www.anchorterminal.com/compare/caddy-app-vs-leon.md)
- [Caddy vs Lindy](https://www.anchorterminal.com/compare/caddy-app-vs-lindy.md)
- [Caddy vs Lobby](https://www.anchorterminal.com/compare/caddy-app-vs-lobby-os.md)
- [Caddy vs nanobot](https://www.anchorterminal.com/compare/caddy-app-vs-nanobot.md)
- [Caddy vs NanoClaw](https://www.anchorterminal.com/compare/caddy-app-vs-nanoclaw.md)
- [Caddy vs Dots](https://www.anchorterminal.com/compare/caddy-app-vs-openai-dots.md)
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- [Caddy vs Poke](https://www.anchorterminal.com/compare/caddy-app-vs-poke.md)
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- [Gemini Spark vs Skydive](https://www.anchorterminal.com/compare/gemini-spark-vs-skydive.md)
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- [Dots vs Skydive](https://www.anchorterminal.com/compare/openai-dots-vs-skydive.md)
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- [OpenDuet vs Skydive](https://www.anchorterminal.com/compare/openduet-vs-skydive.md)
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- [Skydive vs Tomo](https://www.anchorterminal.com/compare/skydive-vs-tomo.md)
- [Skydive vs Town](https://www.anchorterminal.com/compare/skydive-vs-town.md)
- [Skydive vs Wajo (Fo)](https://www.anchorterminal.com/compare/skydive-vs-wajo.md)
- [Skydive vs Zapia](https://www.anchorterminal.com/compare/skydive-vs-zapia.md)
- [Skydive vs ZeroClaw](https://www.anchorterminal.com/compare/skydive-vs-zeroclaw.md)
- [Skydive vs Zo Computer](https://www.anchorterminal.com/compare/skydive-vs-zo-computer.md)
- [Caddy vs Natura tinyNature](https://www.anchorterminal.com/compare/caddy-app-vs-natura.md)
- [Caddy vs Pally](https://www.anchorterminal.com/compare/caddy-app-vs-pally.md)
- [Caddy vs Tomo](https://www.anchorterminal.com/compare/caddy-app-vs-tomo.md)
- [Caddy vs Wajo (Fo)](https://www.anchorterminal.com/compare/caddy-app-vs-wajo.md)
- [Lobby vs Skydive](https://www.anchorterminal.com/compare/lobby-os-vs-skydive.md)
- [Natura tinyNature vs Skydive](https://www.anchorterminal.com/compare/natura-vs-skydive.md)
- [Pally vs Skydive](https://www.anchorterminal.com/compare/pally-vs-skydive.md)

## 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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Query this catalogue directly over MCP: https://www.anchorterminal.com/mcp (Streamable HTTP, no key). How: https://www.anchorterminal.com/agents/#mcp