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Productivity · head to head

BoldSign vs Day One

BoldSign logo

BoldSign

Productivity

eSignature API and app for developers and teams

From
Free
Rated
-
Full reviewWebsite
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

The short version

  • Each has a real cost: BoldSign premium plan: additional envelopes cost $0.50 each after 250/month limit; 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.
  • Prices and features above were last checked on 1 September 2026.

Where they differ

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

Attributes where BoldSign and Day One differ
AttributeBoldSignDay One
Pricing modelsubscriptionFree tier plus subscription
PlatformsWebiOS, Android, macOS, Web

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 BoldSign

Nothing recorded that Day One does not also cover.

Only in Day One

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

What people use each for

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

BoldSign

  • eSignature automationnot Day One
  • Contract signingnot Day One

Day One

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

Where each one falls short

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

BoldSign

  • Premium plan: additional envelopes cost $0.50 each after 250/month limit
  • Monthly billing costs 60-85% more than yearly billing (no 40% discount)
  • Enterprise API requires minimum $30/month

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.

Pricing, plan by plan

BoldSign

Free
  • EssentialFree
    • 25 envelopes/month
    • 2 templates
    • No additional users
  • Growth$5/month yearly
    • 50 envelopes/month
    • 10 templates
  • Business$15/month yearly
    • Unlimited envelopes
    • Unlimited templates
    • SSO
  • Premium$99/month yearly
    • 250 envelopes/month
    • Unlimited users

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

Which should you pick?

Choose BoldSign if

  • You want to start without paying.
BoldSign review

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

Questions people ask

Is BoldSign or Day One better?
Neither clearly leads. BoldSign starts at Free and Day One at Free, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, BoldSign or Day One?
BoldSign starts at Free and Day One at Free.
Does BoldSign or Day One run on more platforms?
BoldSign runs on Web. Day One runs on iOS, Android, macOS, Web.
Can I use BoldSign for free?
Both have a free tier, so you can try either at no cost before committing.
What is BoldSign best used for?
BoldSign is most often used for esignature automation, contract signing. Of those, esignature automation and contract signing are not what Day One is typically brought in for.
What can BoldSign do that Day One cannot?
Day One covers Multiple journals, Rich entries, End-to-end encryption, On This Day.

Answered from the vendors’ own pages

BoldSign: Does BoldSign offer a free plan?

BoldSign's Essential plan is free and includes 25 envelopes per month, 2 templates, and basic features like audit trails and authentication.

Source
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.

BoldSign: How much does the BoldSign Growth plan cost?

The Growth plan costs $5 per month per user with annual billing or $15 per month per user with monthly billing, including 50 envelopes/month per user.

Source
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.

BoldSign: What are the overage fees for BoldSign's Premium plan?

The Premium plan includes 250 envelopes per month for $99-$138/month, with additional envelopes charged at $0.75 per envelope.

Source
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.

BoldSign: How much does BoldSign charge for API access?

BoldSign's Enterprise API costs $0.75 per envelope with a minimum charge of $30/month and includes 40 envelopes and 2 application users.

Source
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