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Question

Automatic Device Enrollment Certificate Upload Error

  • January 13, 2026
  • 9 replies
  • 98 views

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Unable to complete file upload. fiie contents does not match file type in Jamf when uploading an automated device enrollment token from apple business manager

9 replies

ktrojano
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  • Jamf Heroes
  • January 13, 2026

@jakekiser Does the server token file you are trying to upload have a .p7m extension?


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  • Author
  • New Contributor
  • January 13, 2026

Yes it does.


ktrojano
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  • Jamf Heroes
  • January 13, 2026

Have you tried downloading another token file?


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  • Author
  • New Contributor
  • January 13, 2026

I have tried multiple times. I even tried a new PEM file.


ktrojano
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  • Jamf Heroes
  • January 13, 2026

Are you using a Mac and Safari? I believe I encountered  this issue before when I was using a Windows computer and switching to a Mac resolved the issue. 


joboo72
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  • Jamf Heroes
  • January 13, 2026
PI-433 (PI149000) Automated Device Enrollment server tokens cannot be successfully uploaded to Jamf Pro when using the Chrome browser. Workaround: Use the Safari or Firefox browser.

It worked for me yesterday in Safari.


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  • Contributor
  • January 14, 2026
PI-433 (PI149000) Automated Device Enrollment server tokens cannot be successfully uploaded to Jamf Pro when using the Chrome browser. Workaround: Use the Safari or Firefox browser.

It worked for me yesterday in Safari.

Thank you for this. Can confirm I was unable to renew by uploading using Chrome (even Incognito). Had to use Safari to go through the entire process (download new Public Key to upload to ASM and download token to then upload to JAMF Pro).


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  • New Contributor
  • January 14, 2026

I can confirm I had this same issue. I was issued a new key from our college computer store after sending them our public key. I went to upload from Chrome on my Windows machine (like I’ve done every year for the past 5+ years) and it gave the error everyone is describing. I had him issue me a new key, tried again, still didn’t work. Then I happened upon this post, booted up my Mac and tried from Safari and it worked. I have to imagine Jamf broke something in a recent update. Thanks to everyone here though for posting about this (with a fix) so quickly.


scelis13
  • New Contributor
  • January 15, 2026

Has anyone been able to resolve this using a Windows machine?

I have tried to redownload the Public Key and Token multiple times now using: MS Edge, Chrome, and Firefox, and still no luck.