The 2027 filing season starts in your mailbox before it starts at the IRS. Your first wave of volume is the organizer run you send yourself, and its replies land in January. So the question worth asking in September is what has to be settled while settling anything is still cheap.
- Your season and the IRS’s season begin on different days. Yours begins with mail you send.
- This year’s dates fall awkwardly. January 31 is a Sunday, March 15 is a Monday, and April 15 is a Thursday. Each one moves where the pressure lands.
- The engagement letter is the fall’s real deadline. Once it goes out in December, what it says is fixed for the season.
- Anything that has to learn your practice learns it before February, on mail that’s cheap to get wrong.
The season starts before the IRS does
The IRS announces the day it starts accepting returns in early January, and in recent years that day has landed in the last week of the month. It’s a real date and it matters for filing. Your mailbox runs on a different one.
Your own season opens earlier, and it opens because you open it. The organizer goes out. The engagement letter goes out. The portal invitation goes out, and the fee change if there’s one. For a practice with four hundred individual clients, that’s four hundred near identical messages inside a few weeks. What comes back is the first real volume of the year. Questions carrying no date. Single forms arriving months ahead of the rest of a file. Silence from the clients you assumed were coming. What to do about that in the quiet weeks is getting your inbox ready before January, which takes the December version apart properly.
The sequencing is the part that matters here. By the time the IRS opens, your January is already spent. The mail you’re handling in the last week of the month is the reply wave to something you sent in the second week of December. Its size was set in December, whatever Washington announces.
Where the 2027 dates fall
You know the deadlines. The column worth writing down is the weekday. The weekday decides which of your days is the last one that can absorb anything, and this year they fall in an awkward pattern.
Friday, January 15. The fourth 2026 estimate. The reminders go out in the first days of January, which puts them in the same week as the organizer replies. In a flat list, the two look alike. Quarterly estimate reminders is where that job lives.
Monday, February 1. January 31 is a Sunday, so the W-2s, the 1099-NECs and the filings that go with them are due on the Monday. The mail shows it on the two days before. Payroll bureaus and brokerages send over the weekend, from addresses no human reads. Monday opens on a batch that arrived while the office was shut. That’s when the 1099s start arriving from both sides, and it’s the first week of the year that punishes a flat inbox.
Monday, March 15. Partnerships and S corporations. A Monday deadline is worse than it looks. The last useful business day for a client to send you anything moves back to Friday the 12th. The weekend before becomes a working one for whoever is finishing the returns.
Thursday, April 15. Individual returns and calendar-year C corporations. The closing stretch is Monday to Thursday, four working days rather than five. The day after is a Friday rather than a weekend. April 16 is Emancipation Day in the District of Columbia, and this year it falls the day after the deadline rather than on it, so the deadline stays where it is. That week from inside a practice is April, when every client is waiting on you at once.
Then the second season, Wednesday, September 15 and Friday, October 15. That’s its own compression, and October, and the second season nobody planned for treats it as one.
Take the deadlines themselves from the IRS when it publishes the season’s calendar. What’s here is the arithmetic sitting underneath them.
What only the fall can settle
Three decisions have a hard edge in the next few months, and each edge is one your own calendar sets.
The first is whether software reads client mail at all. That’s a firm decision rather than an afternoon’s work. It usually takes at least one conversation nobody enjoys, and it runs at its own pace. A practice that opens it in November gets to a decision. A practice that opens it in February runs out of month. The questions worth asking, and the answers a vendor should be willing to give in writing, are in is it safe to use AI on client data. The version a small firm will actually use is a simple AI policy.
The second is the engagement letter, and it’s the one with a real date attached. The letters go out in December. Whatever they say about how the firm handles client information is fixed from then on, for every engagement and the whole season. Changing it afterwards means writing to everybody a second time, in the month you have least appetite for it. If the letter needs a line about AI, November is when that line gets agreed. What to put in your engagement letter about AI has the wording, and more usefully, what a letter cannot carry.
The third is who’s in the season and on what. Firms take on hands for four months. The seasonal preparer, the returning retiree and the contract reviewer all end up inside the mail somehow. Settled in October, that’s an admin task. Settled on February 3, it’s somebody forwarding a client’s documents from a personal address because it was quicker. Why the practice mailbox ends up being the only record of what each client still owes you is running the firm inbox.
Trying anything new before February
There are about twelve weeks between now and December, and December is the last month with any slack in it.
That matters for one reason. Software that ranks or summarizes mail has to work out how one particular practice runs, and the material it has for that is the traffic itself. Which clients get an answer inside the hour. Which threads can sit happily until Thursday. Weeks of it, not days. A start in early December buys six weeks of being wrong about that, on messages with no date attached, and that’s the cheapest kind of wrong available. A start on February 10 buys the same learning laid on top of the season, and it’ll be abandoned by the 14th. What the firm remembers afterwards is that the software failed. What actually went wrong was the month.
The fall is for deciding it, so December is execution rather than evaluation. What to test a product against, and the five kinds of thing sold as AI email to accounting firms, is AI email for accountants. What actually happens to your filters, your signature and your existing address when you connect a mailbox is how to switch to an AI email client. Read that one in October rather than January. Most of the fear of switching turns out to be about things that stay exactly as they are.
What Point does with a season’s mail
Point runs on top of the mailbox the practice already keeps, on Google or on Microsoft. Your mail stays where it is. Your address stays the one four hundred clients already have, in the month you’d least like to announce a new one.
What Point does in a season is narrow, and it’s the same handful of things every day. Point ranks the mail before you sit down, so the first screen of a March morning shows you decisions instead of an arrival order. Every thread carries a plain summary before you open it. That counts for most on the forwarded chains from a client’s bookkeeper, the ones that arrive with nothing written above the attachments. An ask buried in the fourth paragraph of a reply turns into a task with a date on it, and Point does the typing. Whatever you asked a client for is carried as a debt owed to you, and it resurfaces on the day you set for it. The full inventory is on the benefits page, and the version written for a practice is Point for accountants.
How far Point goes is a dial, with a separate setting for each kind of work, and every kind starts on review. The seasonal reading of that is worth stating plainly. Raise the routine settings first: filing, ranking, and an acknowledgment you’ve already worded. Keep anything that puts words in front of a client under your own eye for a first March. At the top of a setting, Point acts without asking, and that’s the reason to put a setting there at all. Everything Point did is listed with a timestamp, and you can reverse most of those entries straight from the list. One limit sits outside that list. Once a message reaches somebody else’s server it counts as sent, and that holds for every piece of software there is. That whole decision is setting how much your inbox does on its own.
Two limits belong in a piece about getting ready. Point holds no job list, and can’t see how much work is already stacked in front of any preparer, so your cut-off date stays your call, and so does which returns get finished. And if what the firm wants is a status board showing which of eleven documents have arrived for each client, an email client is not that, for the reasons in why a document register belongs on one list. Both are reasonable things to want, and it pays to be clear about which of them you’re buying.
Point is in private beta and priced per seat. Firms join from the waitlist on the home page, and the fall is the stretch of the year when a firm can join and still have a December to settle into.
Common questions
Is it too late to change how we handle mail before this season?
No, and the fall is the last point at which it’s comfortably early. The constraint is the learning. Anything reading your mail needs weeks of ordinary traffic to learn your practice, and December is the only stretch of the year that supplies those weeks with nothing depending on them. Decide in the fall, run it in December, be settled by the second week of January.
When does the 2027 filing season open?
The IRS announces the date it starts accepting returns in early January, and in recent years that’s landed in the last week of the month. Your own season opens earlier and on its own schedule, on whichever day in December the organizer run goes out. That second date decides what January feels like, and it’s the one you control.
Does our engagement letter have to say anything about AI?
That depends on your firm and your state, and what to put in your engagement letter about AI sets out what a letter can and cannot carry. What’s seasonal about it is the timing. The letters go out in December, so it’s a November decision. A change made after they’re signed means a second mailing, in the worst possible month for one.
What if we start something and it does not suit us in March?
Then you find out in the two weeks that tell you the most, which is an argument for connecting in December. The address, the archive and the account you already pay for stay as they are while Point is connected, so stopping leaves you where you started. How to switch to an AI email client covers the way out as well as the way in.
Should we just wait for the 2028 season?
That’s a real option, and worth naming plainly. A firm already mid-way through a software change of its own is better off reaching February with one thing changed instead of three. So is a firm with an unfinished partner conversation about client data. The cost of waiting is one more season of the arrangement you have. The cost of going ahead is a January spent learning something, and only one of those two is recoverable.
The short version
Your season starts in December, when the organizer run goes out. The IRS opening date in late January arrives into a mailbox that’s already busy. This year the deadlines land on a Friday, a Monday, a Monday and a Thursday. The weekday is the part worth writing down, because it decides which day is the last one that can absorb anything. Three things have to be settled this fall rather than in the season: whether software reads client mail at all, what the engagement letter says before it goes out in December, and who is inside the mailbox for four months. Anything that has to learn your practice should meet December’s mail rather than March’s. The season stays the same length either way. What changes is that it becomes predictable, which on March 11 is close enough to the same thing.