AI Assistant (Ask AI)

Ask plain-language questions about your data and your aircraft's manuals — and tell the assistant to handle bookings for you, hands-free.

Overview

The Ask AI tab gives you a chat interface that understands your specific aircraft and group. It does three things:

• Answers questions about your data — who flew when, how many hours you’ve logged this year, what you’ve spent on fuel, what maintenance is due, who has the airplane booked this weekend.
• Answers questions about your aircraft’s manuals — engine hot start, emergency gear extension, GPS setup, autopilot operation, performance settings — drawn from the catalog manuals you’ve bookmarked plus any documents you’ve uploaded.
• Executes requests on your behalf — book a flight, cancel a booking, move a booking. More agentic actions (logging flights, filing squawks, marking maintenance complete) are queued.

Ask AI is available on paid plans (Solo and Club).

What It Can Do

Answer questions about your data

The assistant reads from your group’s flight log, maintenance items, squawks, bookings, currency events, and your member profile. For owners, admins, and treasurers, it can also read the ledger, member balances, and planned expenses.

Try questions like:

• “How many hours did Rob fly last quarter?”
• “How much have we spent on fuel this year?”
• “What maintenance is coming up in the next month?”
• “Who has the airplane booked this weekend?”
• “Show me my night currency status.”

Answer questions about your bookmarked manuals

The assistant searches the catalog manuals you’ve bookmarked into your Documents Library — 130+ POHs, engine manuals, avionics operating manuals, and supplements that we’ve pre-parsed for text search. Bookmark the ones that apply to your aircraft and you can ask about their content immediately.

Documents you’ve uploaded yourself to the Documents Library appear in your library but aren’t yet AI-searchable — auto-indexing of uploads is on the roadmap.

Try questions like:

• “What’s the hot start procedure for my engine?”
• “Walk me through emergency gear extension.”
• “How do I activate a flight plan on the GTN 750?”
• “What are the autopilot’s altitude-hold limits?”
• “What’s the right power setting for 65% power at 9,000 ft at 2300 RPM and standard temperature?”

If a manual hasn’t been processed yet (e.g., scanned PDFs that haven’t been OCR’d), the assistant will tell you and suggest uploading a text-searchable version.

Execute requests on your behalf

The assistant can also create, reschedule, and cancel bookings for you. Ask it to book a flight; it checks availability, summarizes what it’s about to do, and asks you to confirm before writing anything to the calendar.

Try requests like:

• “Book the airplane Saturday afternoon for a trip to Friday Harbor.”
• “Cancel my Saturday booking.”
• “Move my June 14 booking to June 15.”

You can manage only your own bookings; owners and admins can manage any booking. Cancellation and reschedule both require an explicit yes — destructive actions never happen on a single tap.

More agentic actions are queued — logging completed flights, filing squawks, marking maintenance complete, recording payments — each following the same confirm-before-write pattern.

How to Use It

1. Tap the Ask AI tab in the bottom navigation
2. Type a question, or tap one of the suggestion chips
3. The assistant responds, often with the source — manual page, ledger entry, or flight ID — so you can verify

For follow-up questions, you can keep typing — the assistant remembers the conversation context. To start fresh, tap the refresh icon in the top right.

Voice Input

Tap the microphone icon on your phone’s keyboard to dictate the question instead of typing it — both iOS and Android keyboards have one. The assistant works equally well with dictated and typed questions.

Privacy & Data Access

The assistant’s answers are based on your group’s data plus your aircraft’s documents. To make sure you understand what it sees:

• For regular members: the assistant has access to flight logs, bookings, squawks, maintenance items, currency events, and your own profile. It does not have access to the group ledger or member balances (those are admin-only).
• For Owners, Admins, and Treasurers: the assistant additionally has access to the ledger, member balances, planned expenses, and bank-balance summaries.
• For Mechanics: the assistant has access to maintenance items, squawks, and the Documents Library — same as the mechanic’s regular access — not the flight log or ledger.

Conversations are not shared between members. Each member’s chat history is private to them.

How Your Data Is Handled

Your data is sent to Anthropic’s Claude API to generate responses. We use prompt caching to keep costs down and provide context efficiently. Your data is not used to train future models under Anthropic’s standard API terms.

The assistant can make changes only through the confirmation-gated agentic actions described above (currently bookings). For everything else — logging a flight, posting a bill, adding a maintenance item — changes still happen through the regular app screens.

When to Use the Assistant vs. the Regular Screens

The assistant is best when:

• You’re looking up procedural information from a manual — much faster than scrolling through a 200-page PDF
• You want a calculation across many records — “How much fuel have we burned?” beats opening the ledger and adding up entries by hand
• You’re not sure where in the app something lives — ask, and it’ll point you there
• You want to verify your understanding — “What does the POH say about leaning at altitude?”

The regular screens are better when:

• You’re doing data entry the assistant doesn’t yet handle — flight logging, maintenance entry, and squawk filing are all on their dedicated screens for now (queued for the assistant in upcoming releases)
• You want to browse, sort, or filter a list
• You need to see something visual (calendar, charts, Gantt timeline)

Use both together — the assistant is most useful as a quick-question companion to the app, not a replacement for it.

Limitations

The assistant is helpful but not perfect:

• It does not reliably handle multi-variable performance lookups that require interpolating across two or three POH chart axes at once — takeoff distance across pressure altitude + temperature + weight, climb performance at non-standard conditions, density-altitude-adjusted landing distance, and so on. For those, use the POH directly.
• It can also occasionally misread numbers from older scanned manuals. Always verify safety-critical numbers (W&B, takeoff/landing distance, fuel) directly against the original document.
• It’s not a substitute for a CFI or A&P mechanic. Use it as a reference tool, not a final authority on training or maintenance decisions.
• It can’t see information that isn’t in 5-by-5 or in your aircraft’s documents. If you ask about a service bulletin you haven’t uploaded, it can only tell you what’s publicly known.

Quotas and Cost

Ask AI is included in paid Solo and Club subscriptions at no extra cost. To keep costs predictable, each member gets 25 questions per day. In a Club, every member has their own 25 — they don’t share a pool. The quota resets at midnight UTC; if you hit it, the assistant tells you exactly what happened and how long until reset.

If you’re consistently hitting the cap and Ask AI has become central to how you use 5-by-5, drop us a line at support@blueskyapplications.com — we’d love to hear about it and may raise your limit individually.

What’s Coming Next

Active areas of development:

• More agentic actions beyond bookings — logging a flight, adding a maintenance item, or posting a squawk via natural language. Bookings shipped first; the rest follow the same confirm-before-write pattern.
• Group-uploaded document indexing — extending Ask AI search to documents members have uploaded to the group (not just the public manuals catalog)
• Multi-modal POH support — better extraction from scanned and figure-heavy manuals

See Getting Started for an overview of the rest of 5-by-5.