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Productivity · head to head

HEY vs iLovePDF

HEY logo

HEY

Productivity

Flat annual subscription email service from 37signals, with its own hey.com domain and a distinctive Screener

From
$99/year
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

  • Only iLovePDF has a free tier, so it costs nothing to try first.
  • Each has a real cost: HEY there is no free tier and no monthly billing option, so trying it beyond the trial means committing to a full year upfront.; 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: HEY covers The Screener, iLovePDF covers Single-purpose tools.
  • Prices and features above were last checked on 1 September 2026.

Where they differ

Only the attributes on which HEY and iLovePDF actually diverge.

Attributes where HEY and iLovePDF differ
AttributeHEYiLovePDF
Starting price$99/yearFree
Pricing modelPer user per monthfreemium
Free tierNoYes
PlatformsMac, Windows, Web, iOS, AndroidWeb

Identical on both: 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 HEY

  • The Screener
  • Imbox, Feed and Paper Trail
  • Reply Later stack
  • Focus and Reply mode
  • Screen sharing style clips
  • No tracking pixels

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.

HEY

  • Someone who wants to replace Gmail or iCloud Mail entirely with an email service built around approving senders before they reach the inboxnot iLovePDF
  • A user overwhelmed by newsletters and receipts who wants them automatically separated from person to person conversationnot iLovePDF
  • A family that wants shared but individually addressed email under one annual plannot iLovePDF
  • A small company wanting HEY for Work on its own domain with the Screener model for the whole teamnot iLovePDF

iLovePDF

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

Where each one falls short

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

HEY

  • There is no free tier and no monthly billing option, so trying it beyond the trial means committing to a full year upfront.
  • Adopting HEY means changing your actual email address, not just installing a new client, which is a bigger migration than switching apps on an existing address.
  • The Screener and categorisation model is a real departure from a standard inbox, and some users take time to adjust or find it gets in the way for high volume mail.
  • Short vanity addresses carry steep additional annual fees, up to 999 US dollars a year for a two character address.
  • It does not connect to or manage existing Gmail, Outlook or iCloud accounts, so it cannot be used as a general client the way Mimestream or Apple Mail can.

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

HEY

$99/year
  • HEY for You$99/year
    • One hey.com email address
    • Screener, Imbox, Feed and Paper Trail
    • Billed annually only, no monthly option
  • HEY for Families$179/year
    • Covers up to five family members
    • Same features as HEY for You per member
  • HEY for Work$12/month
    • Per user, for organisations on a company domain
    • Admin controls for a team

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 HEY if

  • You need the screener.
  • You work on Mac, Windows, Web, iOS, Android.
  • You also want imbox, feed and paper trail.
HEY 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 HEY or iLovePDF better?
Neither clearly leads. HEY starts at $99/year and iLovePDF at Free, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, HEY or iLovePDF?
iLovePDF has a free tier; the other does not. Paid plans start at $99/year for HEY and Free for iLovePDF.
Does HEY or iLovePDF run on more platforms?
HEY runs on Mac, Windows, Web, iOS, Android. iLovePDF runs on Web.
Can I use iLovePDF for free?
Yes. iLovePDF has a free tier, so you can try it without paying. HEY starts at $99/year.
What is HEY best used for?
HEY is most often used for someone who wants to replace gmail or icloud mail entirely with an email service built around approving senders before they reach the inbox, a user overwhelmed by newsletters and receipts who wants them automatically separated from person to person conversation, a family that wants shared but individually addressed email under one annual plan, a small company wanting hey for work on its own domain with the screener model for the whole team. Of those, someone who wants to replace gmail or icloud mail entirely with an email service built around approving senders before they reach the inbox and a user overwhelmed by newsletters and receipts who wants them automatically separated from person to person conversation are not what iLovePDF is typically brought in for.
What can HEY do that iLovePDF cannot?
HEY covers The Screener, Imbox, Feed and Paper Trail, Reply Later stack, Focus and Reply mode. iLovePDF covers Single-purpose tools, Format conversion, Text recognition conversions, File size limits.

Answered from the vendors’ own pages

HEY: Can I use HEY with my existing Gmail address?

No. HEY provides its own hey.com email address; it is not a client layered over an existing Gmail or other account.

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.

HEY: Is there a free plan?

No. HEY offers a trial but bills annually only, with no free tier and no month to month option for individuals.

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.

HEY: What is the Screener?

A feature that holds mail from any new sender until the user explicitly approves them, before it appears in the inbox at all.

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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