Typeless vs Wispr Flow: Which AI Dictation App Wins in 2026?
Typeless and Wispr Flow both provide system-wide AI dictation on Mac, Windows, iOS, and Android, but their current plans no longer support the old claim that only Wispr Flow has an enterprise tier. Typeless offers the larger simple free allowance and stronger published zero-retention language; Wispr Flow offers the lower month-to-month Pro price, more granular individual, student, business, and enterprise plan choices, and a separate meeting Notetaker on Mac.
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Best Fit 2026
Best choice depends on use case
Use the verdict below to match each tool to your workflow.
Typeless
FreemiumTypeless combines dictation, rewriting, translation, Ask anything, personal vocabulary, and app-specific tones across desktop and mobile. Free includes 8,000 words per week. Pro adds unlimited words, enhanced accuracy, priority access, team administration, centralized billing, and usage analytics. Enterprise adds SSO, SCIM and JIT provisioning, domain controls, audit logs, enforced HIPAA controls, BAA availability, volume discounts, flexible terms, and priority support.
Best For
Pros
- ✓8,000 free words per week
- ✓Mac, Windows, iOS, and Android support
- ✓100+ languages, translation, app-specific tones, personal dictionary, and Whisper mode
- ✓Published zero cloud retention for dictation content, subject to the documented voluntary-feedback exception
- ✓Pro team management, centralized billing, and usage analytics
- ✓Enterprise SSO, SCIM/JIT, domain controls, audit logs, enforced HIPAA controls, and BAA availability
Cons
- ✗$30/member/month on monthly billing; $12/month equivalent requires annual prepayment
- ✗Free accounts use standard accuracy and standard access during high demand
- ✗Cloud processing is required
- ✗Enterprise pricing is not public
- ✗Diagnostic or pseudonymized content may be collected when a user voluntarily submits feedback or consents
Wispr Flow
FreemiumWispr Flow provides cross-platform dictation with more than 100 languages and plan-specific free limits. Pro adds unlimited dictation and team features; Business and Enterprise extend administration and security controls. Its meeting Notetaker is currently Mac-only, Android remains Beta, and privacy, cloud sync, and model-training settings have separate controls.
Best For
Pros
- ✓$15/user/month Pro option without annual commitment
- ✓Mac, Windows, iPhone, and Android dictation in 100+ languages
- ✓Unlimited Pro dictation and Command Mode
- ✓Student and Business prices are published
- ✓Team billing and shared vocabulary without a minimum Pro seat count
- ✓Enterprise SAML SSO, SCIM, audit logs, MDM, domain controls, and HIPAA-ready BAA support
Cons
- ✗Free limits differ across desktop, iPhone, and Android
- ✗Android remains Beta and does not have full feature parity
- ✗Notetaker is currently Mac-only
- ✗Privacy Mode, model-training opt-out, cloud sync, and local retention are separate controls
- ✗Enterprise price is not public
Feature-by-Feature Comparison
| Feature | Typeless | Wispr Flow |
|---|---|---|
| Free tier | Free: $0 / member / month | Free: $0 / month |
| Pro price (annual) | Free: $0 / member / month · Pro Annual: $144 / member / year · Pro Monthly: $30 / member / month · Enterprise: Custom · Student Discount: 50% off Pro | Free: $0 / month · Pro Monthly: $15 / user / month · Pro Annual: $144 / user / year · Student: $7.50 / month or $72 / year · Business: $30 / seat / month or $288 / year · Enterprise: Custom |
| Pro price (monthly) | Free: $0 / member / month · Pro Annual: $144 / member / year · Pro Monthly: $30 / member / month · Enterprise: Custom · Student Discount: 50% off Pro | Free: $0 / month · Pro Monthly: $15 / user / month · Pro Annual: $144 / user / year · Student: $7.50 / month or $72 / year · Business: $30 / seat / month or $288 / year · Enterprise: Custom |
| Enterprise | Custom; SSO, SCIM/JIT, domain controls, audit logs, enforced HIPAA controls, BAA | Custom; SAML SSO, SCIM, audit logs, MDM, domain controls, HIPAA-ready BAA |
| Platforms | macOS, Windows, iOS, Android | Mac, Windows, iPhone, Android Beta; Notetaker Mac-only |
| Languages | 100+ | 100+ |
| Privacy model | Cloud processed; dictation content discarded, with voluntary-feedback exception | Cloud processed; privacy, training, sync, and local-retention controls are separate |
| Student offer | 50% off Pro for eligible new subscribers; desktop checkout | $7.50/month or $72/year; current guide lists a student trial |
| Team features | Pro team management, billing, invoices, and usage analytics | Pro team billing and shared dictionary; Business and Enterprise options |
Our Verdict
Neither product wins every category. Annual Pro pricing is the same at $144, both now offer enterprise controls, and both cover the four major platforms. Typeless is stronger for a simple high-allocation free tier and its published zero-retention posture; Wispr Flow is stronger for monthly price flexibility, plan variety, shared vocabulary, and Mac meeting notes.
Choose Typeless if…
Choose Typeless if the 8,000-word free allowance, its published dictation-data retention policy, translation tools, or Typeless-specific team and Enterprise controls best match your workflow. It is no longer accurate to describe Typeless as lacking an enterprise plan.
Choose Wispr Flow if…
Choose Wispr Flow if you want the lower $15 month-to-month Pro option, published Student and Business prices, shared team vocabulary, or its Mac meeting Notetaker. Confirm device-specific limits and feature parity before rollout.
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Current pricing
Tool-page data verified 2026-08-24Typeless: Free: $0 / member / month · Pro Annual: $144 / member / year · Pro Monthly: $30 / member / month · Enterprise: Custom · Student Discount: 50% off Pro
Current USD pricing: Free $0/member/month with 8,000 words per week; Pro $12/member/month billed yearly ($144/member/year) or $30/member/month billed monthly; Enterprise is custom-priced. Verified students who have not yet subscribed can receive 50% off Pro through desktop checkout. The current public pricing and billing pages do not promise a standard Pro trial.
Wispr Flow: Free: $0 / month · Pro Monthly: $15 / user / month · Pro Annual: $144 / user / year · Student: $7.50 / month or $72 / year · Business: $30 / seat / month or $288 / year · Enterprise: Custom
Current USD pricing: Free $0 with platform-specific weekly limits; Pro $15/user/month or $144/user/year ($12/month equivalent); Student $7.50/month or $72/year; Business $30/seat/month or $288/seat/year; Enterprise is custom. Annual pricing is about 20% lower than monthly. Checkout currency and price can vary by country. Trial length depends on signup path, referral, student status, team enrollment, or promotion.
This block follows the current pricing data shown on each tool page. Editorial ratings and verdicts are reviewed separately.
Frequently Asked Questions
Is Typeless or Wispr Flow cheaper?
Their annual Pro price is the same at $144. Wispr Flow is cheaper month-to-month at $15 versus Typeless at $30. Typeless provides 8,000 free words per week, while Wispr Flow applies different free limits by platform.
Which has the better free plan?
Typeless is simpler and more generous for desktop users at 8,000 words per week. Wispr Flow documents a 2,000-word soft and 5,000-word hard desktop cap, separate iPhone limits, and currently unlimited Android use; those platform rules should be rechecked before choosing.
Do both offer enterprise plans?
Yes. Typeless now publishes an Enterprise plan with SSO, SCIM/JIT, domain controls, audit logs, enforced HIPAA controls, and BAA availability. Wispr Flow also offers Enterprise with SAML SSO, SCIM, audit logs, MDM, domain controls, and HIPAA-ready BAA support.
Do both work on Android?
Yes, but the maturity differs. Typeless publishes Android as a supported platform. Wispr Flow supports Android but currently labels it Beta and documents feature differences from desktop and iPhone.
How do their privacy approaches differ?
Both use cloud processing. Typeless states that dictation audio, transcripts, and edits are discarded after processing, except content voluntarily submitted through feedback or consent. Wispr Flow documents separate controls for privacy mode, model-training opt-out, cloud sync, and local retention.