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Cannot open attachments in Outlook after update to 11.6.6.

Did recently update MacOS to 11.6.6. and now I cannot open attachments. Outlook says 'The file “<name of file>[1].pdf” couldn’t be opened because you don’t have permission to view it. ... '


I do open Outlook Temp directory (in private/var/folders/.../com.microsoft.Outlook/Outlook Temp), the attachment is saved there but is Locked. Viewing file info shows me with Read&Write privilege as I have admin rights everywhere.

When I manually untick Locked status, then I can open the attachment from the Outlook. But I have to do it with each attachment which makes it almost unusable. On next start of Outlook after being quit the problem appears again as the Outlook Temp directory is completely deleted on Outlook exit.


Saving the attachment works, then the file is not Locked. I can also Quick look the attachment, but in quick look I don't see extended word formatting, notes in PDF etc.


This problem appeared immediately after update to 11.6.6. - before the update, everything was ok.


MacBook Pro with Touch Bar

Posted on May 18, 2022 2:10 AM

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Posted on May 19, 2022 12:32 AM

Same problem here. But I did some testing:

The problem only occurs when preview is running. If I close preview before clicking onto the attachment it will open. The second one will fail again.

Same for other attachment types than pdf: But: With xlsx Excel ask for permission instead of failing to open.


Renaming the temporary directory so Outlook has to create a new one doesn't solve the problem.

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99 replies

Jun 2, 2022 6:55 AM in response to pcbjr

pcbjr wrote:
What's the link to file a bug report with Apple, and also with Microsoft (though the latter will say it is Apple since it was all fine until the new update)

They can say that all they like, but if it's only affecting Microsoft's products, then it's quite possible they've just never been using Apple's APIs correctly, and some bugfix in the OS is now making that a problem.

Jun 2, 2022 11:23 AM in response to pcbjr

I have exactly the same issue and have spent about 2 hours on the phone to Microsoft support level 2 and their answer was to download the attachments before opening them which is doable but highly impractical. My iMac won't let me upgrade to Monterey. I have a MacBook Pro running Monterey and it doesn't have the problem at all and neither does my crappy old Windows PC that's about a hundred years old. I'm guessing it's also a one way street and there's no going back to 11.6.5.

Jun 2, 2022 11:37 AM in response to Marc JJ

Marc JJ wrote:

I'm guessing it's also a one way street and there's no going back to 11.6.5.

I had the same question. The answer seems to be "only with a clean installation," which sounds simple enough. Heck, I clean-installed 11.6.6 hoping it would help.


Now, you may ask, how exactly does one acquire a 11.6.5 Installer.app? That's a lot trickier. I never found an official download source, but I did find an Apple CDN link to what purports to be the 11.6.5 installer on a random website.

Jun 3, 2022 12:52 AM in response to bercakir

So finally, I upgraded to Monterey and all problems gone. I think mac user who are able to do this upgrade this is the only and (swift) fix than waiting Apple and Microsoft’s solutions. I have Early 2015 MacBook Air. So far I don’t see any performance related problems. So may be this can be encouraging for whom are hesitating older Macs may have suffer due to latest MacOs. Good luck to all !

Jun 3, 2022 4:46 AM in response to atulfromMH

I posted earlier about having the same problem so I rolled up my sleeves and fixed it. I had to download an installer file for Big Sur 11.6.5 and then make a bootable USB stick from it. Then I had to delete my Mac's HD drive using 'disk utility' and use the USB stick to do a fresh install of 11.6.5. There are plenty of YouTube clips of how to do it and this is what I followed.


I am pleased to say that after installing 11.6.5 and the Office 365 suite, everything is back to normal so it definitely IS the Big Sur 11.6.6 update that was causing the issue.


It's taken all morning to sort this and luckily I have nothing stored on my local drive (otherwise I would have needed to back this up first) but the end result is what I wanted.


Thank you Apple for causing a big pain in the arse to a lot of people!

Jun 3, 2022 4:48 AM in response to Marc JJ

Sorry, almost forget to say that I have also unchecked the 'keep my Mac updated' box which I never normally do and also I have stopped Microsoft updates too. I know this isn't the done thing but I am sure once Microsoft and Apple have sorted themselves out, it will okay to keep everything updated automatically again.

Jun 5, 2022 8:02 PM in response to lipo2lipo

I have this problem too. I tried giving Outlook, Word, Excel, PowerPoint full disk access from Privacy Settings. It no longer ask permissions.


As for PDF, when I switch the default app to Adobe Acrobat, no issue. Only with Preview as the default. But today I revert to Preview as default app to open PDF, it didn't ask for permission, strange.

Jun 7, 2022 2:19 AM in response to Qit45_2

apple shame! It's a sneaky way to force you to change your computer even if it's still fully functional! I went back to Catalina and everything works perfectly! Apple You must publish that MacBook Pro (Retina, 15-inch, Mid 2014) is not upgradeable to Big Sur! Now I have the serious problem that my Photo library that was opened with Big Sur no longer opens with the version of Photos that runs on Catalina. I lost several days of work trying to fix this mess not caused by me! Apple have been a customer for over thirty years but I am very disappointed by this unfair behavior!

Jun 7, 2022 2:20 AM in response to Qit45_2

apple shame! It's a sneaky way to force you to change your computer even if it's still fully functional! I went back to Catalina and everything works perfectly! Apple You must publish that MacBook Pro (Retina, 15-inch, Mid 2014) is not upgradeable to Big Sur! Now I have the serious problem that my Photo library that was opened with Big Sur no longer opens with the version of Photos that runs on Catalina. I lost several days of work trying to fix this mess not caused by me! Apple have been a customer for over thirty years but I am very disappointed by this unfair behavior!

Jun 7, 2022 2:37 AM in response to lipo2lipo

Apple shame!

I have updated to the Big sur v. 11.6.6. and suddenly everything was no more working:

Mail, preview, Outlook, Airdrop... a terrible mess!

It's a sneaky way to force you to change your computer even if it's still fully functional!

I have made all the efforts to fix it, spending our with support and re installing Os from scratch! Nothing to do!

I went back to Catalina and everything works perfectly!

Apple You must publish that MacBook Pro (Retina, 15-inch, Mid 2014) is not upgradeable to Big Sur! Now I have the serious problem that my Photo library that was opened with Big Sur no longer opens with the version of Photos that runs on Catalina.

I lost several days of work trying to fix this mess not caused by me! Apple I have been a loyal customer for over thirty years but I am very disappointed by this unfair behavior!

Jun 7, 2022 6:14 AM in response to ItalBale

I contacted Apple about AirDrop’s asking for permissions to transfer from my iPhone to late 2014 intel iMac. The phone rep solved the problem by instructing me to go to internet settings on each device, delete my network Not just change it or turn it off- delete it. Restart the devices. Chose my network, It worked. Airdrop is working. Just be sure that you know your network password before you delete your network.

Jun 8, 2022 4:15 PM in response to MartinFfn

I am having the exact same issue but with Mac Mail. So it's likely not an Outlook issue. The issue appeared after updating to Big Sur 11.6.6. Someone else in the thread said that it only did this when Preview is already open, and I've confirmed the same. If I double click an attachment with Preview closed, it will launch preview and open the attachment. But if Preview is already open, I will get the permissions error. I will file my own report with Apple.

Cannot open attachments in Outlook after update to 11.6.6.

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