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Productivity · head to head

Day One vs iLovePDF

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
iLovePDF logo

iLovePDF

Productivity

Browser toolbox for merging, splitting, compressing and converting PDFs, processed on the vendor's servers

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.; iLovePDF processing happens on the vendor's servers, so every file is uploaded to a third party, which rules the tools out for client documents, personal data and anything under a confidentiality obligation no matter how briefly the file is held.
  • They diverge on capability: Day One covers Multiple journals, iLovePDF covers Single-purpose tools.
  • Prices and features above were last checked on 1 September 2026.

Where they differ

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

Attributes where Day One and iLovePDF differ
AttributeDay OneiLovePDF
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 iLovePDF

  • Single-purpose tools
  • Format conversion
  • Text recognition conversions
  • File size limits
  • Desktop and mobile applications
  • Digital signatures
  • PDF/A output
  • No account needed

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 iLovePDF
  • A person keeping a travel journal that auto-attaches location and weather to each entrynot iLovePDF
  • Someone who wants encrypted entries kept separate from an unencrypted general journalnot iLovePDF
  • A user who wants automated daily writing prompts and On This Day nostalgia reviewnot iLovePDF

iLovePDF

  • Combining scanned pages into a single PDF or splitting a large document occasionally, without buying a desktop PDF editor.not Day One
  • Compressing a PDF that a mail system or an upload form refuses to accept.not Day One
  • Converting a scanned document into an editable Word or Excel file, which needs the paid text recognition tools.not Day One
  • A small office needing simple PDF operations across several machines without a per-seat desktop licence.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.

iLovePDF

  • Processing happens on the vendor's servers, so every file is uploaded to a third party, which rules the tools out for client documents, personal data and anything under a confidentiality obligation no matter how briefly the file is held.
  • The free tier is bounded by file size per tool rather than by feature, with Office conversions capped at 15 MB, so the large scanned documents most likely to need converting are precisely the ones most likely to be refused.
  • The conversions that require text recognition, meaning scanned PDF to Word or Excel, are held for the paid plan, and those are the conversions people genuinely struggle with, while the free ones mostly handle files that were digital already.
  • It is a per-account consumer subscription with no organisational administration, so a company that comes to depend on it ends up with staff holding personal subscriptions and no control over what is uploaded or by whom.
  • The API is a separate product with its own pricing, so a workflow prototyped by hand on the website cannot simply be automated under the same subscription and has to be costed again.

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

iLovePDF

Free
  • BasicFree
    • Access to essential iLovePDF tools
    • Limited document processing
    • 1 account
  • Premium$7/month
    • Full access to all iLovePDF tools
    • Unlimited document processing
    • 1-25 accounts
  • Premium Annual$48/year
    • Same as Premium plan
    • 42% discount compared to monthly billing
  • Business$null/mo
    • Custom pricing (contact vendor for quote)
    • Scalable solutions for businesses
    • 25+ accounts

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 iLovePDF if

  • You need single-purpose tools.
  • You want to start without paying.
  • You also want format conversion.
iLovePDF review

Questions people ask

Is Day One or iLovePDF better?
Neither clearly leads. Day One starts at Free and iLovePDF at Free, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Day One or iLovePDF?
Day One starts at Free and iLovePDF at Free.
Does Day One or iLovePDF run on more platforms?
Day One runs on iOS, Android, macOS, Web. iLovePDF 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 iLovePDF is typically brought in for.
What can Day One do that iLovePDF cannot?
Day One covers Multiple journals, Rich entries, End-to-end encryption, On This Day. iLovePDF covers Single-purpose tools, Format conversion, Text recognition conversions, File size limits.

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.

iLovePDF: Do I need an account?

Not for the basic free tools, though they are subject to per-tool size limits and restrictions on batch processing.

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.

iLovePDF: Is it safe for confidential documents?

Files are uploaded to the vendor's servers for processing. For client material, personal data or regulated documents, use a tool that works locally on the machine instead.

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.

iLovePDF: What does Premium add?

Access to every tool including text-recognition conversions and PDF/A, much larger files, unlimited processing, desktop and mobile applications, digital signatures, workflows and no adverts.

iLovePDF: Can I use it inside my own application?

Only through the separate developer API, which is priced independently, so plan the automation cost separately from the consumer subscription.

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