Hiro development journal

Real-world assistant capability boundary audited

2026.07.23 at 15:49:11 America/Los_Angeles Published Machine-readable JSON

Executive summary

Audited Hiro's current calendar, mailbox, task, reading-list, reminder, memory, and web-update capabilities to distinguish simulated evidence from production readiness.

The stateful simulator has substantial safety and recovery coverage, including three consecutive six-of-six canonical workflow passes and a thirty-of-thirty adversarial run. Those results used fictional state and do not prove live account operation.

Privacy-preserving connector probes found that the currently configured Google and iCloud read-only integrations are not operational, while Outlook is not configured. Hiro therefore cannot currently be treated as a reliable real-calendar or mailbox assistant.

Work completed

Live connector audit

Diagnosed

Confirmed that Google Calendar and Gmail have read-only tool implementations and local credential artifacts, but both current provider probes failed at token refresh.
Confirmed that iCloud Calendar has a read-only CalDAV implementation and configured settings, but the provider rejected the current authorization.
Confirmed that Outlook Calendar remains unconfigured.
No connector permission, credential, account data, event, message, or provider configuration was changed.

Calendar and email action boundary

Simulation complete; production absent

Production tools can only read calendar and Gmail summary data when credentials are healthy. There is no registered production tool for creating, changing, or deleting calendar events, inviting attendees, drafting live email, or sending email.
The simulated harness supports conflict discovery, proposal and draft creation, exact-scope approvals, calendar creation, email sending, stale-state recovery, idempotency, rejected and expired approvals, and adversarial failures.
All simulated external writes operate on fictional in-memory state and never reach a provider.

Tasks and reading lists

Storage foundation only

Typed local storage functions and schemas exist for tasks, reading items, provenance, and approval records.
The user-facing production tool registry does not expose task or reading-list create, update, list, or review operations.
Task and reading-list mutations are exercised in the simulated harness, not through Hiro's live conversational tool surface.

Proactive assistance and current-information updates

Partial

A reminder scheduler and an on-demand web-search tool exist, and the web-search provider is configured.
There is no production topic subscription, source-quality policy, briefing compiler, delivery schedule, or user review surface for proactive wider-internet updates.
Curiosity and improvement records mention morning briefings as a possible experiment, but this is not a deployed user capability.

Step 3 campaign gate

Incomplete

The valid Step 3 session completed only P1 calibration: thirty-seven of forty fresh cases passed, with no infrastructure or invariant failures.
Phases P2 through P7 were not completed. The persisted summary still says running even though its deadline passed, so this is an incomplete campaign rather than evidence for Step 4.
The campaign remains hermetic and did not authorize or test live provider writes.

Decisions and reasoning

Do not infer production capability from synthetic perfect scores; validate each real connector and action boundary separately.
Restore reliable read-only access before implementing any provider write path.
Expose persistent local task and reading-list operations before attempting cross-provider autonomous workflows.
Introduce live writes progressively: read-only shadowing, draft/proposal artifacts, exact user approval, then one bounded provider action with reconciliation and audit.
Do not enable proactive internet briefings until topics, sources, cadence, delivery, and opt-out controls are explicit.

Validation and evidence

Check	Status	Result
Google Calendar read-only connectivity	failed	A privacy-preserving historical-range probe reached the configured integration but the provider rejected credential refresh. No calendar data was retained or published.
Gmail read-only connectivity	failed	A privacy-preserving empty historical query reached the configured integration but the provider rejected credential refresh. No message data was retained or published.
iCloud Calendar read-only connectivity	failed	A zero-day CalDAV probe reached the configured integration but authorization was rejected. No event data was retained or published.
Outlook Calendar configuration	not configured	No Microsoft client configuration or token artifact is currently present.
Synthetic stateful assistant evidence	passed previously	The retained evidence includes three consecutive six-of-six Qwen canonical workflow runs and a thirty-of-thirty structurally novel adversarial report with no unauthorized write.
Step 3 diversity campaign	incomplete	P1 completed at thirty-seven of forty; P2 through P7 and campaign closeout are absent, while the expired session summary remains marked running.

Current state

Hiro has a strong simulated agent harness but does not currently have reliable live calendar or mailbox access.
Production calendar and Gmail tools are read-only by design and presently blocked by authentication failures.
Tasks and reading lists have typed local persistence foundations but no registered conversational tools.
Reminders and on-demand web search exist; proactive source-backed briefings do not.
No production calendar write, attendee invitation, live email draft/send, or cross-tool approval execution path is deployed.

Next steps

Reauthorize Google read-only access and repair iCloud authorization, then run privacy-preserving live read smoke tests and a multi-day shadow period.
Add production task and reading-list list/create/update tools backed by typed local storage, with provenance, idempotency, and user-visible audit history.
Add provider-neutral calendar proposals and email drafts that do not perform external writes.
Complete or explicitly close and replace the incomplete Step 3 campaign before using its results as a Step 4 gate.
After stable shadow evidence, request separate approval for the smallest live calendar write pilot; keep invitations and email sending disabled initially.
Design proactive briefings as an opt-in product with controlled topics, trusted-source rules, cadence, quiet hours, delivery channel, and per-item provenance.