How I Checked These Prices

I did not trust one source. I read the live Typeless pricing page and its pricing FAQ, the dictation-limit page in the help center, and the Data Controls and Privacy pages. Then I compared the numbers with independent pricing write-ups and with Wispr Flow’s published rates.

Where Typeless’s own pages said nothing (the exact free word cap, student terms, refund rules), I tell you where the number came from. Many pricing blogs are written by companies that sell a rival dictation app, so I treat those as directional.

This is a pricing and fine-print review, not a stopwatch test of every feature. The checking here is document-level: what each plan says it includes, and where the fine print disagrees with the headline.

Typeless AI Pricing in 2027: Every Plan at a Glance

Prices were verified on October 23, 2026 and hold for 2027 unless Typeless changes them. I will update this post if they move.

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Prices are per member. When you add a teammate, they take an open seat first. If none is free, a new seat is added and you pay a prorated charge for the rest of the billing cycle. Remove someone mid-cycle and the seat stays usable until renewal, with no refund for the unused time.

The pricing page headline promises you will “save 1 day per week” on Pro. I would treat that as marketing. It is not something I could verify from any document.

What Changed in Typeless Pricing Since My Last Update

Several details in the older version of this post no longer match the live page. These are the corrections:

• Three plans, not two. Enterprise now sits on the pricing page with SSO, SCIM, audit logs and a Business Associate Agreement.
• Linux is listed. The desktop line-up is macOS, Windows and Linux, plus iOS and Android on mobile.
• Pro adds more than a word limit. It now lists enhanced accuracy, priority access during high demand and Cloud Sync.
• HIPAA wording is softer. The page says “HIPAA-ready.” Enforced HIPAA controls and a BAA are listed under Enterprise. My earlier line saying every plan was simply “HIPAA compliant” went too far.
• The free word number is gone from the page. It only says “limited words,” so the 8,000 figure now comes from Typeless’s other material.
• Dictation length is capped at six minutes per the help center, which the old post never mentioned.

Typeless Free vs Pro: Feature Comparison

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Look at that list and one thing stands out. The free plan keeps almost every feature. You are paying Pro prices for volume, accuracy, sync and team tools, not for a different product.

Typeless does not explain what “enhanced accuracy” means in practice. It does not publish a word error rate for either tier. That is a fair question to ask before you pay for a year.

How Much Is 8,000 Words a Week, Really?

Here is the arithmetic, since “limited words” means nothing until you convert it:

• About 1,600 words per workday on a five-day week.
• Around 100 emails at 80 words each.
• Roughly six first drafts of 1,300-word blog posts.
• About an hour of continuous speech at a normal speaking pace.

That sounds like plenty until you count everything. Slack replies, notes, prompts to AI tools, captions and drafts all add up. A writer who dictates full drafts will cross the line fast. Someone who only dictates quick replies may never see it.

I could not find a published rule for when the weekly counter resets. Check the usage display in the app before you plan a heavy week around it.

Which plan fits you?

Monthly vs Yearly: Where the Break-Even Sits

Typeless charges two and a half times as much per month on monthly billing. $30 × 12 comes to $360, against $144 for the yearly plan.

Four monthly payments cost $120, so month-to-month wins if you stay four months or fewer. The fifth payment pushes you to $150, past the full-year price. Over three years the gap is $432 on yearly billing against $1,080 on monthly billing, a difference of $648.

One more catch. A third-party read of Typeless’s terms (the August 2026 version) says refunds are limited to cases where the law or your app store requires one. So do not buy the year on day one. Use the free plan on real work for a week first.

Typeless vs Wispr Flow: A Price Check

Wispr Flow is the rival people compare most often. Its rates below come from several independent trackers, so confirm them on Wispr’s pricing page before you buy.

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On yearly billing the two cost exactly the same. The differences sit elsewhere. Typeless’s free allowance is roughly four times Wispr’s desktop cap, but Wispr’s monthly Pro costs half as much.

Two clarifications, because people mix these up. AssemblyAI is a speech-to-text API for developers, not a Typeless alternative. And if you want meeting recordings and summaries rather than dictation, read my guide on what an AI note taker actually does, or my Lindy AI review for inbox and meeting follow-ups.

For the feature side of the story, my full Typeless AI review covers what the app does day to day.

Discounts, Credits and Gift Cards

These details come from Typeless’s student, referral and gift-card pages as summarised by a third-party write-up. Confirm them at checkout.

• Students: reported at 50% off Pro, valid on desktop checkout only. See the Typeless student page.
• Referrals: reported as $5 of Pro credit for the friend, and $5 for you once they dictate 2,000 words. Desktop checkout only. Details on the referral page.
• Gift cards: reported to unlock one year of Pro with no expiry date.
• Trial: the pricing page does not advertise a Pro trial. The free plan is your trial.
• Lifetime plan: none that I could find.

If you are a student who dictates essays, also read my roundup of AI tools for rewriting academic papers so you know where the line sits for your school.

Pricing Quirks and UX Flaws Worth Knowing Before You Pay

The headline price is only half the story. These are the details I found in the fine print and help pages:

1. Each dictation stops at six minutes

The help center says a single dictation is capped at six minutes. At five minutes, a 60-second countdown appears on the Typeless bar. If you hit the limit, Typeless saves what you have said so far to History. One competitor blog claims nine minutes. Trust Typeless’s own help page over that.

2. The free word cap is not on the pricing page

The page says “limited words” and never gives a number. I found 8,000 in Typeless’s other material and in several reviews, so I use it here with that note.

3. App Store prices are hard to read

One pricing write-up reports that the iPhone listing shows Typeless Pro purchases at $30.00, $60.00 and $143.99 without saying what each covers. It also notes that a referral FAQ mentions a quarterly plan that the pricing page omits. Check what an option renews at before you tap Buy.

4. Discounts do not follow you to your phone

Student codes and referral credits are reported as desktop-checkout only. Subscribing inside the iOS or Android app may cost you more.

5. There is no offline mode

Audio is processed on Typeless’s cloud servers. No connection, no dictation. Plan for that if you write on planes or in patchy signal areas.

6. Payment methods are narrow on the FAQ

The pricing FAQ lists four card brands: Visa, Mastercard, American Express and Discover. Enterprise accounts can use invoicing. If you rely on another payment method, test the checkout before you commit.

Privacy and Compliance: What Each Claim Means

Typeless’s Data Controls page (updated August 25, 2026) says voice audio is not stored and that dictation data is not used for model training by Typeless or any third party.

Read the next sentence on that page too. Audio and contextual data are processed in real time on cloud servers and then discarded. So “zero data retention” does not mean “on-device.” It means cloud processing followed by deletion. Your dictation history is what stays on your device.

The pricing page lists GDPR compliance, ISO 27001 compliance and “HIPAA-ready.” Enforced HIPAA controls and a Business Associate Agreement sit under Enterprise. If you handle protected health information, ask for the BAA in writing before you dictate anything. “HIPAA-ready” is not a signed agreement.

Typeless also publishes a subprocessor list on its trust center. Read it if your employer cares which vendors touch audio. If privacy is your main filter across AI tools generally, my Duck AI review looks at a chat tool built around that idea.

Typeless AI Pros and Cons

Who Should Pick Which Plan

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If you are building a writing income, my guide to freelance writing jobs for beginners shows how quickly word volume adds up. And dictation will not fix weak structure, so the essentials in writing are worth a re-read.

Is Typeless Pro Worth It? My Take

I like the yearly price. I do not like the monthly one.

At $12 a month, Pro is easy to justify if you write every day. At $30, it feels like a nudge toward the annual plan, and I suspect that is the point. The month-to-month price is double Wispr Flow’s.

If I were buying today, I would start on Free and track one week of real dictation. If I stayed under the cap, I would stay free. If I hit it twice, I would go yearly and stop thinking about it.

Two things would worry me. The six-minute cap would interrupt long brain-dumps, and the cloud-only design would rule it out when I am offline. If you already pay for an AI assistant, check my Claude AI pricing guide to see what your whole stack costs before adding another subscription.

FAQ

How much does Typeless cost in 2027?

Typeless Pro costs $12 per member per month billed yearly ($144 a year), or $30 per member per month billed monthly. Free is $0 and Enterprise is custom. These prices were checked on October 23, 2026.

Is Typeless free?

Yes. Every new account starts on the Free plan, which includes Translate, Ask anything, a personal dictionary, tones for each app, Whisper mode and 100+ languages, with a weekly word limit.

What is the Typeless free word limit?

About 8,000 words a week, according to Typeless’s own published material. The pricing page only says “limited words,” so check the usage counter in the app.

Does Typeless have a student discount?

Typeless is reported to offer 50% off Pro for students at desktop checkout. Verify the terms on its student page before you pay.

Does Typeless have a lifetime plan?

No. I found only Free, Pro (monthly or yearly) and Enterprise. A gift card for one year of Pro is the closest thing to paying once.

Does Typeless work offline?

No. Typeless processes audio on its cloud servers and discards it after returning the text, so you need an internet connection.

Is Typeless HIPAA compliant?

The pricing page says “HIPAA-ready,” and lists enforced HIPAA controls and a Business Associate Agreement under Enterprise. Get the BAA in writing before you dictate patient information.

How long can I dictate at once?

Six minutes per dictation, according to the Typeless help center. A 60-second countdown starts at five minutes, and the text so far is saved to History.

Which devices does Typeless support?

macOS, Windows, Linux, iOS and Android.

Can I get a refund on Typeless Pro?

Only in limited cases. A third-party summary of the terms says refunds are issued when the law or the app store requires them. You can cancel under Subscription on the Account page in the app.

Conclusion

Typeless Pro is good value on yearly billing and poor value on monthly billing. That is the whole pricing story.

The free plan does most of the work for light users. Pro makes sense when you hit the weekly cap, when you want Cloud Sync, or when you manage a team. Enterprise is only for companies that need SSO, audit logs and a signed BAA.

Start free, count your words for a week, then pick yearly or walk away. Do not pay $30 a month unless the project really is short.

This post contains affiliate links. If you buy through them, I may earn a commission at no extra cost to you. Plan details were checked on October 23, 2026 against Typeless’s own pages and can change, so confirm the price at checkout.