Sync iCloud and OneDrive/ Sharepoint/Teams (Office 365) folders

Good morning Power Users! I’m part of a new start up and we are currently using iCloud to organize our files. However, we use Office 365 for our communication and productivity needs. I’m wondering and am so far confused about what software would best sync my iCloud folders with the OneDrive/Sharepoint/Teams ecosystem. The reason I’m doing this is as we grow I’m not confident in iCloud’s ability to grow with us. Currently I’m evaluating Hazel (I just purchased the new Filed Guide but it did not answer my questions), AnyDrive, and ChronoSync Express. Thanks in advance for your input.

Are you needing one way sync (iCloud → OneDrive) or two way (iCloud <-> OneDrive) ?

one way from iCloud to OneDrive.

I haven’t used OneDrive a lot but it seems to function the same as any local cloud storage folder (iCloud/Google Drive). I’ve used Chronosync to sync folders, etc. for years but Hazel should do the job also.

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thanks for finding this @WayneG !

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@MacSparky I assume #hazel is your first choice for this workflow challenge, send word.

Why sync them? Why not go all-in Microsoft 365?


Great question and the answer is… the founder of the start up started the organization on her iMac. She is very productive and resists making the change cold turkey. If I was on site all the time I believe I could manage the friction points or SNAFUs but I’m not. My goal is to have the files sync; then start her off using the @teams app for one or two projects. Then migrate the balance of projects after a satisfactory comfort level is achieved. @wweber what are your thoughts on this implementation plan?

First time that I’ve heard of anydrive, how do you like it?

I tried it a couple of years ago but it was buggy. I’ve not implemented it in this instance and am hesitant to try it again mainly because of @MacSparky enthusiasm for #hazel

I believe you could put her iMac’s OneDrive and SharePoint folders on her iCloud Drive.

Are there any features that she is using in iCloud Drive that aren’t available in Microsoft 365? How will you be using Teams in the organization?

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Teams will be the platform on which all work is performed and shared. Specifically, the ability for individuals to create documents share those documents for review have the documents approved and then deliver the documents to their destination will happen in teams.

Additionally there is a hope that the unified platform that teams promises will enable quick flyover and or drop in by other members of the team to the lifecycle of a document.

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I think you’re on the right track getting her to use the Teams app to access and share files with other people.

You can set up OneDrive and SharePoint/Teams to sync to folders in iCloud Drive with the OneDrive app. I just tested it and it works. Though, that doesn’t really matter if she’s accessing stuff through the Teams app instead of Finder.

I wish Apple was more transparent about where Mac OS actually puts the iCloud Drive folder on the hard drive. It would be nice to be able to sync iCloud Drive to another service.

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