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Productivity · head to head

Day One vs SignWell

Day One logo

Day One

Productivity

Journalling app for iOS, Android and Mac now sold as a subscription after years as a one-time purchase

From
Free
Rated
-
Full reviewWebsite
SignWell logo

SignWell

Productivity

Electronic signature service priced per sender, with unlimited documents on paid plans

From
Free
Rated
-
Full reviewWebsite

The short version

  • Each has a real cost: Day One it moved from a one-time purchase to a subscription after the Automattic acquisition, so long-term cost is materially higher than the original pricing implied.; SignWell the free plan stops at three documents a month, which makes it a trial rather than a tier, so any genuine use converts to a paid seat within weeks.
  • They diverge on capability: Day One covers Multiple journals, SignWell covers Per-sender pricing.
  • Prices and features above were last checked on 1 September 2026.

Where they differ

Only the attributes on which Day One and SignWell actually diverge.

Attributes where Day One and SignWell differ
AttributeDay OneSignWell
Pricing modelFree tier plus subscriptionfreemium
PlatformsiOS, Android, macOS, WebWeb

Identical on both: starting price (Free), free tier (Yes), user rating (Not yet rated), category (Productivity).

What each one covers

Drawn from each product's published feature list. An absence here means we hold no record of it - not that the product lacks it.

Only in Day One

  • Multiple journals
  • Rich entries
  • End-to-end encryption
  • On This Day
  • Cross-platform sync
  • PDF and Day One export

Only in SignWell

  • Per-sender pricing
  • Free signers
  • Free plan
  • Templates
  • Audit trail
  • Automatic reminders
  • In-person signing
  • Bulk send and template links

What people use each for

The jobs each tool is most often brought in to do.

Day One

  • Someone wanting a private daily journal with photos that syncs between phone and laptopnot SignWell
  • A person keeping a travel journal that auto-attaches location and weather to each entrynot SignWell
  • Someone who wants encrypted entries kept separate from an unencrypted general journalnot SignWell
  • A user who wants automated daily writing prompts and On This Day nostalgia reviewnot SignWell

SignWell

  • A small business sending a steady flow of contracts from one or two people, where per-envelope pricing elsewhere adds up faster than a seat would.not Day One
  • Replacing print, sign and scan for client agreements, offers of employment and consent forms.not Day One
  • Embedding signing into your own product through the API without committing to enterprise pricing first.not Day One
  • Repeated onboarding paperwork sent from a template with automatic chasing rather than manual reminders.not Day One

Where each one falls short

Documented limitations, not opinions. Every one is a constraint you would hit in normal use.

Day One

  • It moved from a one-time purchase to a subscription after the Automattic acquisition, so long-term cost is materially higher than the original pricing implied.
  • The free tier caps at one journal and 25 photo entries, which is restrictive enough that anyone journalling seriously for more than a few weeks needs to pay.
  • End-to-end encryption is opt-in per journal rather than on by default, so users have to actively choose it and understand which journals are protected.
  • Cancelling Premium after using multiple journals or heavy photo storage can leave content viewable but with sync and some features disabled, so people should export before cancelling.
  • As an Automattic product, its roadmap sits behind a company whose primary focus is WordPress and Tumblr, not journalling specifically.

SignWell

  • The free plan stops at three documents a month, which makes it a trial rather than a tier, so any genuine use converts to a paid seat within weeks.
  • Pricing is per sender, so an organisation where many people occasionally need to send something either buys seats for staff who send a handful of documents a year or funnels everything through one person and creates a bottleneck.
  • Templates are rationed by tier, at one on free and five per sender on the entry plan, and templates are what makes the tool worth using at all, so the practical entry point is a tier above the headline price.
  • It is a smaller vendor in a category where signed agreements must be retrievable years later, so the safe practice is downloading every signed document and its audit certificate into your own storage rather than relying on the account still existing.
  • It provides standard electronic signatures rather than acting as a qualified trust service provider, so any transaction requiring a qualified electronic signature under European rules needs a different supplier alongside it.

Pricing, plan by plan

Day One

Free
  • FreeFree
    • One journal
    • Up to 25 photo entries
    • Basic sync
  • Day One Premium$3.99/month
    • Unlimited journals and photos
    • End-to-end encryption
    • On This Day and audio transcription
  • Day One Premium Annual$34.99/year
    • Same as monthly Premium at a lower effective rate

SignWell

Free
  • FreeFree
    • 1 sender
    • 1 template
    • 3 documents per month
  • Light$10/month
    • Annual pricing: $10/month (monthly: $12/month)
    • 1 sender
    • 5 templates per sender
  • Business$30/month
    • Annual pricing: $30/month (monthly: $36/month)
    • 3 senders
    • Unlimited templates and documents
  • Enterprise$null/custom
    • Custom pricing for teams of 50+
    • High volume support
    • Advanced compliance needs

Which should you pick?

Choose Day One if

  • You need multiple journals.
  • You want to start without paying.
  • You work on iOS, Android, macOS, Web.
  • You also want rich entries.
Day One review

Choose SignWell if

  • You need per-sender pricing.
  • You want to start without paying.
  • You also want free signers.
SignWell review

Questions people ask

Is Day One or SignWell better?
Neither clearly leads. Day One starts at Free and SignWell at Free, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Day One or SignWell?
Day One starts at Free and SignWell at Free.
Does Day One or SignWell run on more platforms?
Day One runs on iOS, Android, macOS, Web. SignWell runs on Web.
Can I use Day One for free?
Both have a free tier, so you can try either at no cost before committing.
What is Day One best used for?
Day One is most often used for someone wanting a private daily journal with photos that syncs between phone and laptop, a person keeping a travel journal that auto-attaches location and weather to each entry, someone who wants encrypted entries kept separate from an unencrypted general journal, a user who wants automated daily writing prompts and on this day nostalgia review. Of those, someone wanting a private daily journal with photos that syncs between phone and laptop and a person keeping a travel journal that auto-attaches location and weather to each entry are not what SignWell is typically brought in for.
What can Day One do that SignWell cannot?
Day One covers Multiple journals, Rich entries, End-to-end encryption, On This Day. SignWell covers Per-sender pricing, Free signers, Free plan, Templates.

Answered from the vendors’ own pages

Day One: Is Day One still a one-time purchase?

No. Since the 2021 Automattic acquisition it is sold as Day One Premium, a subscription. Older lifetime purchasers were grandfathered but new users pay a subscription.

SignWell: Do signers need an account or a licence?

No. Recipients open a link, sign and are done, with no account and no cost. You pay only for the people who send documents.

Day One: Is encryption on by default?

No, end-to-end encryption is an option users turn on per journal, not a default for all entries.

SignWell: What does the free plan actually allow?

Three documents a month, one sender and one template, along with a small monthly allowance of API documents. It does not include custom branding or bulk send.

Day One: Can I export my entries if I cancel?

Yes, PDF and native Day One export formats are available regardless of subscription status, though some sync and premium features stop working.

SignWell: Is an electronic signature legally binding?

Electronic signatures are recognised for most commercial agreements under the relevant American and European frameworks, and SignWell records an audit trail. Certain instruments are excluded by statute, and anything requiring a qualified signature needs a qualified provider.

SignWell: How hard is it to leave?

The signed documents are ordinary PDFs you can download with their certificates, so the records move easily. Your templates and the workflows built around them do not.

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