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Productivity · head to head

BoldSign vs Ulysses

BoldSign logo

BoldSign

Productivity

eSignature API and app for developers and teams

From
Free
Rated
-
Full reviewWebsite
Ulysses logo

Ulysses

Productivity

Distraction-free writing application for creative professionals

From
$5.99/month
Rated
-
Full reviewWebsite

The short version

  • Only BoldSign has a free tier, so it costs nothing to try first.
  • Each has a real cost: BoldSign premium plan: additional envelopes cost $0.50 each after 250/month limit; Ulysses no free tier available
  • Prices and features above were last checked on 30 August 2026.

Where they differ

Only the attributes on which BoldSign and Ulysses actually diverge.

Attributes where BoldSign and Ulysses differ
AttributeBoldSignUlysses
Starting priceFree$5.99/month
Free tierYesNo
PlatformsWebMacOS, IOS, IPadOS
FoundedUnknown2003

Identical on both: pricing model (subscription), 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 Ulysses does not also cover.

Only in Ulysses

  • Distraction-free writing
  • Markdown support
  • Syntax highlighting
  • Organization with sheets and groups
  • iCloud sync
  • Dark and light themes
  • Full-screen mode
  • Search and filter

What people use each for

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

BoldSign

  • eSignature automationnot Ulysses
  • Contract signingnot Ulysses

Ulysses

  • Writing and editing on Apple devicesnot BoldSign
  • Cross-device document synchronizationnot BoldSign
  • Markdown-based writingnot 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

Ulysses

  • No free tier available
  • Only subscription model, no one-time purchase option
  • Family Sharing limited to 5 additional members (6 total users)

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

Ulysses

$5.99/month
  • Annual Subscription$39.99/year
    • Ulysses on all Macs, iPads, and iPhones
    • Full iCloud synchronization
    • Frequent improvements and updates
  • Monthly Subscription$5.99/month
    • Ulysses on all Macs, iPads, and iPhones
    • Full iCloud synchronization
    • Frequent improvements and updates

Which should you pick?

Choose BoldSign if

  • You want to start without paying.
BoldSign review

Choose Ulysses if

  • You need distraction-free writing.
  • You work on MacOS, IOS, IPadOS.
  • You also want markdown support.
Ulysses review

Questions people ask

Is BoldSign or Ulysses better?
Neither clearly leads. BoldSign starts at Free and Ulysses at $5.99/month, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, BoldSign or Ulysses?
BoldSign has a free tier; the other does not. Paid plans start at Free for BoldSign and $5.99/month for Ulysses.
Does BoldSign or Ulysses run on more platforms?
BoldSign runs on Web. Ulysses runs on MacOS, IOS, IPadOS.
Can I use BoldSign for free?
Yes. BoldSign has a free tier, so you can try it without paying. Ulysses starts at $5.99/month.
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 Ulysses is typically brought in for.
What can BoldSign do that Ulysses cannot?
Ulysses covers Distraction-free writing, Markdown support, Syntax highlighting, Organization with sheets and groups.

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
Ulysses: What are Ulysses pricing options?

Ulysses costs $39.99 per year (annual) or $5.99 per month (monthly). Student discounts are available. Volume licensing is available for businesses through their licensing portal.

Source
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
Ulysses: Does Ulysses include Family Sharing?

Yes, both annual and monthly Ulysses subscriptions include Apple Family Sharing, allowing up to five additional family members to use Ulysses on their devices at no extra cost.

Source
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
Ulysses: Can I get Ulysses through a subscription service?

Yes, Ulysses is available through the Setapp subscription service as an alternative to direct subscription. Volume licensing is also available for businesses and organizations through their licensing portal.

Source
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
Ulysses: Does Ulysses pricing vary by location?

Prices listed apply to the U.S., and local pricing may differ in other regions. Check your regional App Store for exact pricing.

Source
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