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

Caddy vs Lindy

Lindy scores 32.3 (F) on agent readiness against Caddy's 16.7 (F), and leads in 5 of 7 scored categories. Caddy leads on maintenance & community. 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 LindyCrivello Corp (doing business as Lindy) · Platform F32.3/100#974 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

  • Maintenance & community, 55 against 9

Also in its favour

  • No incidents deducted, where Lindy loses 3 points for them

Watch for

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

Lindy F

Best for Lindy suits a person or small team that lives in Slack and Google or Microsoft mail and wants briefs, drafts, scheduling and meeting notes done on a schedule.

Ahead on

  • Reliability, 24 against 10
  • Schema & documentation, 32 against 10
  • Agent ergonomics, 43 against 0
  • Security & auth, 49 against 0
  • Payments & pricing, 35 against 30

Also in its favour

  • Free to start without a card

Watch for

The integrations page says approval settings apply in shared Slack threads only. Web chat, Slack direct messages, iMessage and SMS are not covered, and reads are never covered.

Score by category

CategoryWeight this runCaddyLindyEdge
Reliability16%201024Lindy +14
Performance10%pendingpendingpendingnot scored in this run
Schema & documentation13%16.21032Lindy +22
Agent ergonomics13%16.2043Lindy +43
Security & auth14%17.5049Lindy +49
Payments & pricing10%12.53035Lindy +5
Task success10%pendingpendingpendingnot scored in this run
Maintenance & community7%8.8559Caddy +46
Transparency & trust7%8.85252even
Negative events≤150-3
TotalF 16.7/100F 32.3/100

Facts side by side

FactCaddyLindy
KindPlatformPlatform
VendorCaddy Technologies Inc.Crivello Corp (doing business as Lindy)
Hosted endpointno (local only)no (local only)
Transports
AuthOAuth or keyOAuth
PricingFreePaid
x402nono
LicenceClosed service under Caddy's Terms of Service (Caddy Technologies Inc., last updated 27 April 2026).Proprietary service under Lindy's Terms of Service. No source is published
Read-only variant documentedyesno
llms.txtyesyes
Last release2026-10-132025-10-21
Terms last updated2026-09-24
Privacy policy last updated2026-09-28
Customer content may train modelsnot found in the text
Terms restrict automated accessyes
Terms restrict benchmarkingyes
Terms or service can change without noticeyes
Arbitration or class-action waiveryes

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.

Lindy

Lindy keeps what it remembers in files the owner can read and edit, and publishes credit prices. Its approval setting applies in shared Slack threads only, so writes asked for by direct message, text or web chat run unasked, which its pricing page does not say. It has no status page, and its changelog stops in October 2025.

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.

Lindy

  1. Treat a request sent by direct message, text or web chat as unguarded. Approval prompts appear in shared Slack threads only.
  2. Run a routine as a dry run before turning it on. A dry run reads real data and sends, posts and writes nothing.
  3. Turn off unused tools after adding an MCP server. Every supported tool arrives switched on, and a large server adds more than a hundred.
  4. Expect a billed seat for anyone who mentions Lindy in Slack. A teammate who joins that way has seven free days first.
  5. Connect only hosted MCP servers on public HTTPS with streamable HTTP, the one kind the docs describe.

Questions

Which is better for AI agents, Caddy or Lindy?

Lindy scores 32.3 (F) on agent readiness against Caddy's 16.7 (F), and leads in 5 of 7 scored categories. Caddy leads on maintenance & community.

Other comparisons with Caddy or Lindy

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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