Moving files to OneDrive turns aliases into exe files

Chris 20 Reputation points
2026-08-16T15:57:58.2766667+00:00

I got a new work computer and so I had to move all my necessary files to OneDrive. On my old computer, all the aliases still look like regular aliases, and they take me to the correct document. On my new computer, all the aliases show up as exe files (or whatever those are in the picture). I tried unlinking and re-linking the new computer from the OneDrive account but it didn't fix this problem (caused others). I'm running Tahoe 26.6.1 on a MacBook M5 Pro.

Screenshot 2026-08-16 at 9.53.11 AM

Microsoft 365 and Office | OneDrive | Other | MacOS
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Allan Solomon Mejia 8,000 Reputation points
2026-08-19T19:52:42.24+00:00

Hello @Chris

Thanks, that clarification helps. What you're seeing actually makes sense given how macOS Finder aliases and the newer OneDrive File Provider implementation interact.

The old Mac can still resolve those aliases because macOS aliases aren't simply text paths. Finder can retain additional information that allows it to locate a target even after the target moves. On the new Mac, however, that historical filesystem relationship isn't necessarily preserved when OneDrive synchronizes the alias itself.

There's another important factor here: on macOS 12.1 and later, OneDrive moved its actual sync location into:

~/Library/CloudStorage/...

Microsoft specifically documents that this path change can cause previously pinned/referenced files to stop working.

So unfortunately, I don't know of a supported OneDrive setting that will automatically rebind dozens of existing Finder aliases to their corresponding files on another Mac. OneDrive synchronizes the alias file, but it doesn't reconstruct Finder's target relationship for the destination Mac.

One thing I'd test before recreating everything:

  1. Make the target OneDrive folders Always Keep on This Device on the new Mac so the underlying files are fully materialized locally. Microsoft confirms that Files On-Demand is integrated with macOS File Provider and that online-only files aren't actually downloaded until required.
  2. Let OneDrive finish syncing completely.
  3. Test several existing aliases again.
  4. Create one new alias on the new Mac, sync it through OneDrive, and test that alias on the old Mac.

That last test is particularly useful because it confirms whether you're dealing with Finder alias portability rather than damaged documents or OneDrive synchronization.

If you have dozens of aliases, I wouldn't manually recreate them yet. If the original and new target locations follow a predictable structure, you may be able to script alias recreation on the new Mac using the filenames/target structure. That's probably a much cleaner solution for three course folders than rebuilding every alias manually.

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  1. Allan Solomon Mejia 8,000 Reputation points
    2026-08-16T17:03:45.1766667+00:00

    Hello @Chris

    This looks less like OneDrive converting your documents into Windows .exe files and more like a macOS alias compatibility/synchronization issue.

    A Finder alias is a special macOS reference to another file or folder rather than the actual document. Apple describes aliases as pointers that open the original item. OneDrive, however, doesn't support syncing symbolic links/junctions, and similar reference-type objects can behave differently after being moved through cloud storage.

    The screenshot supports this: the affected items are only about 1 KB and retain names ending in .pdf alias, .docx alias, etc. That strongly suggests you're looking at the alias files themselves, not converted copies of the original documents.

    I would recommend:

    • Confirm that the actual PDF/DOCX files referenced by those aliases were also migrated to the new Mac.
    • Try creating a new Finder alias to one of the synced documents directly on the new Mac. If that works, the old aliases likely didn't survive the migration correctly.
    • Don't rely on Finder aliases as portable OneDrive shortcuts. Re-create them locally after the underlying files have synchronized.
    • Updating OneDrive is also worthwhile, especially since Microsoft recommends keeping the macOS client current for sync-related issues.

    Unlinking/re-linking OneDrive probably won't repair the existing aliases because the issue is likely with the alias metadata/reference itself rather than the OneDrive account.

    Also, macOS 12.1 and later places the OneDrive sync root under ~/Library/CloudStorage/..., which can affect older references to OneDrive file locations.

    Sharing you references:

    Microsoft – Fix OneDrive sync problems on Mac | https://support.microsoft.com/en-us/onedrive/fix-onedrive-sync-problems-on-mac?

    Apple – Create and remove aliases on Mac | https://support.apple.com/en-afri/guide/mac-help/mchlp1046/26/mac/26?

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