Ulysses Problems & Issues
Real user-reported problems, complaints, and limitations for Ulysses. Based on analysis of 13 signals.
Overall score: 69/100
Issues by Category
Apple-only: No Windows or Android versions
Ulysses is exclusive to Apple devices (macOS, iOS, iPadOS). There are no Windows, Android, or Linux versions and no plans to create them. Writers with cross-platform needs or who work in mixed environments are completely excluded.
Slow development despite subscription revenue
Long-time users say updates are mostly bug fixes and minor integrations rather than major features. Recent 2026 releases did add project templates, Siri/AI support and longer backup retention, so the complaint has softened, but the perception persists among subscribers.
Flawed print/formatting for traditional publishing
An experienced author who produced nine books found Ulysses 'deeply flawed' for print publication, particularly with paragraph indentation handling. Not ideal for writers targeting traditional print formats.
Ulysses requires macOS 15.4 and iOS 26
The current version requires macOS 15.4+ and iOS/iPadOS 26+. Owners of older Macs or iPads can only get an older compatible build if they previously installed Ulysses on that OS with the same Apple Account; those builds miss new features.
Features poorly explained with hidden menus
Features are poorly explained, if at all, and menus and buttons feel hidden. Users must rely on trial and error to discover functionality. The learning curve is steeper than the clean interface suggests.
Ulysses tables only work in Markdown XL markup
Native tables arrived in version 27 (2022), but the (tbl) tag only works with the Markdown XL markup - not plain Markdown, Minimark or Textile'd - and tables don't export to RTF. Users on other markups think tables are missing; images and links still feel awkward compared with WYSIWYG editors.
Controversial switch to subscription angered existing users
Users who bought Ulysses at full price ($45-70) lost their perpetual license when developers switched to subscription. The backlash was significant - long-time users felt betrayed paying again for software they already owned.
Why is Ulysses so expensive? $40/year subscription for a writing app
Ulysses costs $5.99/month or $39.99/year in the US (official pricing page, App Store). For writers who only need a focused editor, a recurring fee compares badly to one-time purchases such as Scrivener or iA Writer. Family Sharing (up to 5 extra members) softens it for households.
Ulysses perpetual license costs $199.99
In 2026 Ulysses added a one-time Perpetual License ($199.99 in the App Store) with no trial. Users on Mac Power Users (Oct 2026) call it expensive and say they don't trust a 'lifetime' promise after the 2017 switch that moved earlier one-time buyers to subscriptions; the help page itself says new features can't be guaranteed indefinitely.
Ulysses sheets disappeared after sync problems
Forum users report whole groups or book content vanishing from the library, usually tied to iCloud sync conflicts. Built-in backups are local to each device and are not iCloud backups; version 41.2 (Oct 2026) now keeps monthly backups indefinitely and retains more hourly/daily/weekly ones.
Ulysses not syncing between Mac and iPhone (iCloud)
Sync relies entirely on Apple's iCloud Drive background services, so Ulysses can't force a sync. Mac Power Users threads report groups with sheets that never download, duplicated groups after conflicts and scene order breaking; fixes range from toggling iCloud to signing out of iCloud on all devices. Some users switched apps after repeated failures.
Poor iPhone experience with cluttered interface
The iPhone experience is subpar - menus look small and sheets appear cluttered. While iPad with keyboard works well, there's no saving grace for iPhone. Not ideal for mobile-first writers.
Ulysses WordPress 'Failed to connect' error
Publishing to self-hosted WordPress uses XML-RPC, which many hosts and security tools (fail2ban, security plugins, nginx rules) block. Users then get 'Failed to connect. Please verify the URL of your blog' and must enable XML-RPC or use a workaround file.
Regret Patterns
Common reasons users regret choosing Ulysses.
Had perpetual license taken away when subscription launched
Users who paid $45-70 for Ulysses lost their perpetual license in 2017 when the app switched to subscription-only. The sense of betrayal was significant - paying again for software they already owned.
Realized need for Windows after committing to Ulysses
Writers who built workflows around Ulysses later needed Windows access for work or collaboration. With no Windows version and no plans for one, their writing system became fragmented.
Expected more updates given subscription price
Users paying a yearly fee expected major improvements and felt they mostly got bug fixes and small features, so the subscription didn't feel proportional to its value.
Lost trust after a sync failure wiped sheets
Writers who trusted iCloud sync found groups or chapters missing after a conflict and learned that Ulysses backups are local per device. Several moved their manuscripts to plain-text apps afterwards.
Library locked inside Ulysses' format
Sheets in the iCloud library aren't plain files, so leaving Ulysses means exporting everything. Users moving to iA Writer or Obsidian regret not using external Markdown folders from the start.
When Ulysses Breaks Down
Specific scenarios where Ulysses fails or underperforms.
Need cross-platform access
Ulysses is Apple-only with no Windows, Android, or web version. Writers who need to work across ecosystems or collaborate with non-Apple users must use different tools or maintain parallel workflows.
Writing requires tables or complex formatting
Ulysses doesn't support tables and handles links/images poorly. Academic, technical, or business writing requiring these elements necessitates different tools like Scrivener.
Publishing to traditional print
Ulysses has been called 'deeply flawed' for print publication. Writers targeting traditional book publishing with specific formatting requirements often find Scrivener more capable.
iCloud sync stops on one device
Because sync runs on Apple's iCloud Drive services, a corrupted iCloud setup or disabled iCloud Drive leaves sheets stuck; Ulysses can't force a sync and fixes often mean signing out of iCloud.
Self-hosted WordPress with XML-RPC blocked
Hosts and security plugins that block xmlrpc.php stop Ulysses publishing with 'Failed to connect' until XML-RPC is allowed.
Older Mac or iPad
New versions need macOS 15.4 / iOS 26; older devices are stuck on legacy builds without new features.