Switching from Dropbox to iCloud


I've been a happy Dropbox subscriber for several years. The service works great, but I've been having some challenges and I want to consolidate my paid cloud services. I'm currently paying for two iCloud accounts and a Dropbox account. I don't see iCloud going anywhere with its seamless iOS backup and photo/video storage, so that's tipping things away from Dropbox. The other advantage is I want to take advantage of macOS's storage optimization.

In recent years, the challenge with Dropbox is syncing to devices with SSD storage. Everything was good when there was hundreds of gigabytes of storage on laptops and terabytes on desktops. It now, however, can be a challenge to sync across all devices when the contents of the cloud accounts could fill up drives. I've managed this by using selective sync, but that's has some frustrating management requirements and usually has me downloading content via the website when needed.

macOS solves this by automatically removing older, larger files as needed from local storage. When local storage gets tight, the local copies of files on iCloud Drive get purged. If you want those purged files, you can download them on-demand. It all works transparently, and with modern reliable broadband, it is usually at most a minor inconvenience waiting a few moments to download.

I've been late to this optimized storage party because this concept is unsettling. The idea that my files are evaporating to the cloud from my computer without my control or even knowledge is unnerving. Still, the sync juggling almost made me switch last year, but Sierra and its updated optimized storage features had just shipped by time my Dropbox subscription was up for renewal. This time around, Apple's solution seems proven and I'm willing to take the leap.

Another problem I'm looking to solve is, at least to my understanding, my Dropbox files must live locally somewhere. My solution has been a desktop with a large storage to house a master of my large files. iCloud Drive doesn't work this way. I could upload 50 GB, it would live in the cloud, and then be offloaded to free up local space when needed.

Apple also recently doubled its $10/mo storage tier. I currently pay for 200 GB to handle basically device backup and my photos/videos. I don't have a need for 2 TB of storage, but I'm liking the idea of not thinking about my storage both in the cloud and locally. The other news out of WWDC this month was that we'll finally be able to share storage plans with Family Sharing. So, I'm expecting I can shut down the second iCloud subscription.

This is a leap of faith, but my safety net is I've got Time Machine backups on various machines. I'll still though will maintain external drives to keep everything safe. My hope is if something goes sideways, everything on my iCloud Drive will have a backup somewhere. Fingers crossed.