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Question

Automatic Device Enrollment Certificate Upload Error

  • January 13, 2026
  • 24 replies
  • 1557 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

24 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.


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  • New Contributor
  • January 16, 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.

I have not been able to get it to work on a Windows device either. Also tried Edge, Chrome, and FireFox.

 

It did finally work when I did it via an iPad


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  • New Contributor
  • January 16, 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.

I have not been able to get it to work on a Windows device either. Also tried Edge, Chrome, and FireFox.

 

It did finally work when I did it via an iPad

I submitted a ticket to Jamf support and was told they are aware of the issue and are expecting it to be resolved in the next release. In the meantime, it appears the only workaround is to do this from either a Mac or an iPad (except iPad minis, can’t log in to ABM on an iPad mini for some reason).


Jordy-Thery
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  • Valued Contributor
  • January 18, 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.

I have not been able to get it to work on a Windows device either. Also tried Edge, Chrome, and FireFox.

 

It did finally work when I did it via an iPad

I submitted a ticket to Jamf support and was told they are aware of the issue and are expecting it to be resolved in the next release. In the meantime, it appears the only workaround is to do this from either a Mac or an iPad (except iPad minis, can’t log in to ABM on an iPad mini for some reason).

Same here. :-) ‘work-around’ is doing it via Safari. 


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  • Contributor
  • January 20, 2026

I usually use Chrome, but in Chrome, the error reads ‘Unable to complete file upload. The file contents does not match the file type’. Edge also gives this error.


So I signed out of everything, opened Safari and downloaded a fresh .p7m token, but the Safari error is ‘The file received was not valid’. Firefox isn’t compatible with ABM to download a token, but also gives this error in Jamf when trying to upload a token downloaded a few mins ago from a different browser.

 

macOS 26.2


jguo
  • New Contributor
  • January 21, 2026

Wild that the solution is using a Mac product...


Niks_i
  • New Contributor
  • January 21, 2026

I tried with Safari (upload a public key generated from chrome btw), create mdm server, download token but it still is different file type.

/ABM-JAMF_Token_2026-01-21T20-05-01Z_smime.p7m: application/pkcs7-mime; name="smime.p7m"; smime-type=enveloped-data, ASCII text, with CRLF line terminators

it still comes with “mime”


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  • Contributor
  • January 22, 2026

Wild that the solution is using a Mac product...

What is the solution? The only thing I’ve not tried yet is using an iPad, and the clock is ticking for me (6 days)


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  • Contributor
  • January 22, 2026

I have just tried on an iPad, iOS 17.7.6, using Safari to sign in to ABM, download a new token, then into JamfPro to uplaod the token, and still get ‘The file received was not valid’. I updated to the latest OS it can take, 17.7.10, and get the same error.


h1431532403240
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Our company encountered a similar problem when trying to help customers replace ADE Certificate.

 

The client uses a Windows computer, and when we use a Mac and Safari, we successfully upload the ADE Certificate.


hiroki.ito
  • New Contributor
  • January 27, 2026

I re-uploaded the Jamf Pro ADE public key to ABM, token upload succeeded using Safari.
(Chrome still failed...)


sdagley
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  • Jamf Heroes
  • January 28, 2026

PSA for folks coming across this thread and getting the ‘The file received was not valid’ error… If the certificate for your JSS has been updated (either by Jamf or yourself if you manage your own certificate) since the last time you successfully downloaded an ADE token you must upload the updated Public Key to ABM/ASM before it will generate a new ADE token that your JSS will accept.


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  • New Contributor
  • February 2, 2026

I just ran into this problem. Looks like a classic line terminator issue. I opened the p7m file in Notepad++, changed from Windows to Mac style line terminators, saved, and Jamf accepted the modified file without error.


After trying all options multiple times.

Using Safari exclusively to:

  1. download a new public key from Jamf
  2. Upload public key to ABM
  3. Download DEP token from ABM 
  4. Upload to Jamf 

Worked.


DT31
  • New Contributor
  • February 3, 2026

After trying all options multiple times.

Using Safari exclusively to:

  1. download a new public key from Jamf
  2. Upload public key to ABM
  3. Download DEP token from ABM 
  4. Upload to Jamf 

Worked.

I confirmed this is the solution that worked for me as well ! 


azercher
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  • New Contributor
  • February 5, 2026

I do not mean to drag this topic back up, but why has no one fixed this to allow someone on a Windows computer or browser (edge) to upload this?