Can I let AI decide which charges to deduct?

No. Deductions are a decision for you, backed by receipts and your state's rules. Use the assistant for wording and arithmetic.

What if the tenant disputes a charge?

Keep the receipts and the dated letter. Your state sets how a dispute is handled, so read the statute before replying.

Should I paste the lease into the chat?

Only the parts you need, with names removed where you can. See the guide on what to redact before pasting a lease into ChatGPT.

AI Security Deposit Letter: What to Check

Yes, but only from your own receipts. Give the assistant the deposit amount, each deduction with its cost and date, and your state's deadline, and it will write a clear itemized letter. It will also happily invent an unlisted charge or miss a deadline, so check every line against a receipt and every date against the statute.

Why a letter like this suits AI

A deposit letter is a list: the deposit held, each charge with a reason and an amount, and the balance returned. The wording is dull and the layout is the work. An assistant produces a clean table in seconds, writes a neutral cover note and keeps the tone calm, which helps if the tenant disputes it.

The risk is the facts. An assistant that is not told a charge will not know it, but one that is asked for "typical" deductions may add some. A deduction you cannot document is a deduction you may lose.

The deadline is the part to check yourself

States set a short clock for returning a deposit or sending a list of charges. Florida, for example, requires a landlord to return the deposit within 15 days after the tenancy ends if there is no claim. If the landlord intends to claim any of it, the landlord must send written notice by certified mail within 30 days, and the tenant then has 15 days to object. Without that notice, the landlord loses the right to claim the deposit (Florida Statutes 83.49). Other states use other numbers and other delivery rules. For a Florida walk through see Florida's 30 day deposit notice.

Do not ask the assistant what your deadline is and trust the answer. Read the statute, write the deadline in your calendar, and give the date to the assistant as a fact.

What to give the assistant

The deposit amount and where it is held.
The move-out date and the forwarding address.
Each deduction as one line: what was done, the amount and the date, with the invoice or receipt in hand.
A rule for what counts as damage and what counts as normal wear, in your own words. See normal wear and tear versus damage.
The statute's required wording, if your state has one.

A prompt to copy

Example prompt: "Write a letter returning a security deposit. Tenant: [name]. Deposit held: $[amount]. Move-out date: [date]. List each deduction exactly as below, in a table with description, date and amount, and add them up. Use only these items. If an item has no receipt, say so in a note to me, not in the letter. Show the refund as the deposit minus the total. Neutral tone, no accusations. Items: [list]."

Example a made-up deposit of $1,500 with a $240 cleaning invoice, an $85 lock rekey and a $60 repair of a torn screen. The deductions total $385 (240 plus 85 plus 60), so the refund is $1,115 (1,500 minus 385). If the assistant's letter shows $1,175, it dropped the $60 item or added wrongly. Always recompute the total yourself.

A five-line check before it goes out

Every line has a receipt or an invoice behind it.
The total of deductions plus the refund equals the deposit.
The date of sending is inside your state's deadline, and the delivery method is the one the statute names.
Nothing in the letter is described as damage that is ordinary wear.
The letter goes to the address the tenant gave you, and you keep a copy.

If the tenant disputes a charge

Stay with the facts. Send the invoice, the date and the photo if you have one, and say in a sentence why the charge is for damage and not for ordinary wear. Ask the assistant for a short reply that does that and nothing else. Do not argue about the tenant's character, and do not add charges after the letter has gone out. If the disagreement goes to a small claims court, the dated letter, the receipts and the move-out photos are what you will bring, so keep them together in one folder.

How DoorKeeping handles it

DoorKeeping keeps each property's deposits held in that property's own books, so the amount you give the assistant matches the ledger. Through a connected Claude or ChatGPT you can ask for a tenant's ledger and work from it. The letter itself is a message you review: the assistant shows you a draft first and sends a message to one tenant only after you say yes.

Sources

Florida Statutes 83.49: Deposit money or advance rent, read Oct 30, 2026
DoorKeeping: Connect Claude or ChatGPT (steps and tools list), read Oct 30, 2026

Questions

Can I let AI decide which charges to deduct?: No. Deductions are a decision for you, backed by receipts and your state's rules. Use the assistant for wording and arithmetic.
What if the tenant disputes a charge?: Keep the receipts and the dated letter. Your state sets how a dispute is handled, so read the statute before replying.
Should I paste the lease into the chat?: Only the parts you need, with names removed where you can. See the guide on what to redact before pasting a lease into ChatGPT.