How to see which leases are expiring soon by asking Claude or ChatGPT
Ask your AI assistant for every lease that ends in the next 90 days, soonest first, with the tenant, the current rent and any balance owed. Then decide each one: renew, change the rent, send a non-renewal notice or plan a turn. The list is read only, so asking costs nothing and changes nothing.
Why lease end dates slip past you
With one or two rentals you remember when each lease ends. With six or sixty you do not, and the dates sit in separate PDFs. The usual result is that a lease runs out, the tenant goes month to month at the old rent, and the window to raise the rent or plan a turn has already closed.
A running list fixes this. The list only needs four things per lease: the unit, the tenant, the end date and what happens next. Everything else can be looked up when you pick that lease up.
What to ask
Once your assistant is connected to your records (see how to connect Claude or ChatGPT), start with one plain question.
- Which leases end in the next 90 days? Show the unit, tenant, end date, current rent and balance, soonest first.
- Which of those are already month to month or past their end date?
- Which of those units have a balance owed right now?
- Which leases end in the same month, so I can see how many turns I might face at once?
The third question matters most. A tenant who owes rent is a different conversation from a tenant who always pays on time, and you want to know before you write either letter.
Sort each lease into one of four outcomes
| Outcome | When it fits | Next step |
|---|---|---|
| Renew at the same rent | On-time tenant, rent already near the market. | Send a renewal offer. See the renewal offer letter. |
| Renew with a rent change | Rent is clearly below or above the market. | Check the notice period your lease and state require before you send the new number. |
| Let it go month to month | You plan to sell or renovate, or are undecided. | Know that month to month usually ends with a shorter notice period, which cuts both ways. |
| Plan a turn | You are not renewing or the tenant is leaving. | Open a turn and book the work early so the unit is not empty longer than it has to be. |
Notice periods and rent change rules differ by state and sometimes by city, so check your lease and local law before you send anything. See the lease renewal timeline for the usual order of events.
Let the assistant draft, then read it yourself
For the leases you decide to renew, ask for a renewal draft with the new dates and rent. A draft is only a draft: you read it, you change what you want, and sending it for signature stays your tap. See AI renewal drafts for what to check before you send.
Example a made-up owner has 12 leases. Five end in the next 90 days. Two tenants always pay on time, one owes a month of rent, one is already month to month and one is moving out. The owner sends two renewal offers, calls the tenant with the balance first, sends a short note to the month to month tenant and opens a turn for the unit being left. Five leases, four different actions, and nothing is missed because the list was in front of them.
How DoorKeeping handles it
DoorKeeping has a leases tool that lists your leases with the soonest end first and shows who is up for renewal. It only reads, so your assistant can run it any time. A renewal draft is prepared for you to look at, and sending it for signature stays your tap on doorkeeping.com. When a lease ends, a unit turn opens by itself so the vacant unit is tracked from the first day. The full list of what your assistant can do is on the connect page.
Sources
- DoorKeeping: Connect Claude or ChatGPT (steps and tools list), read Oct 30, 2026
- Model Context Protocol: Tools (specification), read Oct 30, 2026
Questions
- How far ahead should a landlord track lease expirations?
- Ninety days is a common window. It leaves time to send a renewal offer, give any notice your state requires and book work if the tenant leaves. Check your lease and local law for the exact notice period.
- Can ChatGPT or Claude tell me which leases are ending?
- Yes, once it is connected to software that holds your leases. On its own, a chat assistant does not know your leases. Connected to DoorKeeping, it can list them with end dates, rent and balances.
- What happens if a lease ends and nothing is signed?
- In many states the tenancy continues month to month on the old terms. The rules differ by state, so read your lease and your state's landlord-tenant law.
- Does the assistant send the renewal on its own?
- No. It prepares a draft. You read it and send it for signature yourself.