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Chronicles

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macOS Sierra's Optimized Storage iCloud syncing for Desktop and Documents folders is buggy and may not suit everyone's workflow

So that's it for the era of the big X. Version 10.12 of the operating system that runs the Mac is here, and with it, a new/old name: macOS.

Six Colors Jason Snell

Context & Ripple Effects

When Apple previewed macOS Sierra in June, Optimized Storage with iCloud was pitched as a headline convenience: the system would manage space by syncing files — including entire Desktop and Documents folders — up to iCloud Drive. Now that Sierra has shipped, hands-on reporting shows the reality is rougher.

Six Colors finds the Desktop and Documents syncing buggy and a poor fit for many workflows, and The Verge's Sierra review reaches a similar verdict on the same day, noting Optimized Storage can frustrate and that bundled iCloud storage is too limited to absorb a typical user's files.

First-order effects

  • Users who enable Desktop and Documents syncing face immediate practical risk: buggy behavior around which files live locally versus in iCloud Drive disrupts workflows built on predictable local paths.
  • Apple's default-on framing puts the burden on users to discover and disable the setting, since the feature changes long-standing folder behavior without an obvious opt-out at setup.

Second-order effects

  • With free iCloud tiers too small to hold most Desktops and Documents, the feature functions as an upsell path into paid iCloud storage plans — its usefulness is gated by subscription spend rather than software quality.
  • Bugs at launch undercut adoption of the exact behavior Apple wants normalized, pushing cautious users back to manual storage management and muting the feature's intended effect on device storage pressure.

Third-order effects

  • Sierra marks a structural turn in macOS design: core file management increasingly routes through Apple's cloud services, with the OS acting as a gateway to recurring revenue — a pattern the same release's Siri reinforces, given its lack of third-party tie-ins keeps assistant value inside Apple's ecosystem.
  • If Apple keeps tying fundamental folder behavior to service quality, trust in the Mac's local-first file model becomes the thing at stake each release, making launch reliability a competitive variable rather than a polish detail.

The trend: macOS releases are progressively wiring everyday file management into paid Apple cloud services, with launch quality deciding whether users accept or switch off the new defaults.