Big Sur 11.6.6 permissions issues

There are 3 or 4 threads open on this all since 11.6.6, regarding both Mail and Outlook ... now this seems bigger than just mail apps but something inherent with the security fixes in 11.6.6 and in particular with Preview ... please file a bug report with Apple (use Feedback Assistant) ... this is a major inconvenience and it needs fixing, but that won't happen unless everyone with this issue takes 2 minutes and files a bug report so the matter percolates to the top :~)

Not sure about Mail but in Outlook )or with just stand alone PDFs) the only workaround seems to be quitting Preview, Word, Excel or whatever app is insisting on permissions, then it will open, but the next one won't unless you first quit the app ...

You can give the not working apps more permissions.

It might not be the best/secure solution, but if they are apple apps I think the risk is manageable, bc they

get access again to folders that they had access to before.

Go to Settings -> Security, choose the Full Disk Access Tab and add the Apps with problems. (*)

I did that for Preview (for problems with mail attachments) and Books (so it could open PDFs again).

When Apple releases an Update to fix the issue (11.6.7 I guess) the apps can be removed again.

regards, Claus

(*) I use a german Mac OS, so the names could be different

I did file a bug report with Apple. I noted that the problem was with using Preview to open attachments in both Mail and Outook (I use the latter for work). I also noted that you can "quick view" the attachments without any problem. I also noted that, at least with Mail, I have given Preview "Full Disk Access". So that would seem to allow it to read any folder, whether "temporary" or not. Apparently not.

The work around does seem to work but it is an extra step. I always click on every file I've attached to a draft email to make sure that I've attached the correct file. Quite annoying (and gets confusing) when I have to save a file attached to a draft email before I can make sure it's correct.

Another workaround, much simpler, is to "Open with Acrobat Reader." After 2 decades of using Preview, I am having to retrain myself to do that.

I'm also someone with an older computer (early 2014 Air) that can't upgrade to Monterey. I had only recently upgraded to Big Sur and had been very pleased with how my "vintage" (per Apple) computer was running on it. (The upgrade even cured a wake-from-sleep problem I was experiencing when running on my aging batter.) It was definitely 11.6.6 that has introduced this problem.

I had the same issue with PDFs in mails or PDFs in ibooks since the last update to 11.6.6.

There is a solution or better maybe a fix/work-around.

I have added preview and books in the security settings from Mac OS to have full disk access.

Now I can open the files again, but I do not know if this is the best way to handle that.

It issue looks like a permission problem with the sandbox environment.

The logs look like this for mail attachments:

Sandbox: Preview(11237) deny(1) file-read-data /Users/(Username/Library/Containers/com.apple.mail/Data/Library/Mail Downloads/Attachment.pdf

PDFs in books have a similar issue with a different path:

sandbox: Preview(11237) deny(1) file-read-data /Users/(Username)/Library/Mobile Documents/iCloud~com~apple~iBooks/Documents/PDF.pdf

I don't have adobe and have not used it in 10 years.

The issue is in the print dialog (Which I used several hundred times per day. (I used the example of printing a webpage from safari). The same thing happens in Word and Excel. The issue is not with the application sending the print to pdf. The problem is with Preview being able to access the temporary file that is created.

See the open pdf in preview option highlighted in the screenshot below. - The save to pdf option works because the print spool is saved directly to the location you select. The open pdf in preview option doesn't work because the print spool gets saved to a temporary location Preview cannot access. These temporary files are stored in private/var/folders/v4/....

(I think the rest of the file name is specific to my computer) somewhere in v4 there are temporary folders for each running application ex (com.apple.Safari/printing.random number/) The temporary file is saved in one with the application name under a new folder named print.random number. When I go there I can open the file in preview just fine directly from the temp folder but for some reason Preview cannot open it through the "Open pdf option"

Print dialog. I want to print to pdf using the Open in Preview. After I click "Open in Preview" the following permission errors show. You should be able to replicate this if you have 11.6.6. If anyone doesn't have this problem with version 11.6.6 please let me know.

From Microsoft Word trying to print a word document. - Excel does the same thing.

From Safari trying to print www.google.com

From Safari trying to print www.apple.com

I have a late 2013 Macbook Pro, and had the same problem with the Big SUR update with 11.6.6. I update to Big SUR 11.6.7 this morning and seems to have corrected the problem. No issues now with attachments in email or permissions.

Updated to 11.6.7 and the issue has been resolved. Thank you for the quick fix, Apple.

I have this exact issue as well. I believe it started with the 11.6.6 update for me, but I am not positive.

After a safe boot and a reinstallation of macOS (over top of the existing), there was no improvement, so I deleted the volumes and did a clean install. I signed in to iCloud and installed 1Password before I thought to test, but I believe these steps would reproduce the problem on a fresh install as well:

1. Close Preview if it's open.
2. Open TextEdit and create a document with arbitrary text contents.
3. Print the document to PDF using the menu in the print dialog box, saving the file to ~/Desktop.
4. Right-click the file on the desktop and choose "Open With" and then Safari.
5. Use the overlay button in Safari (near the bottom center of the screen) for "Open in Preview".
6. The document will open correctly in Preview. Close the document window, but not Preview.
7. Click the "Open in Preview" button in Safari again.
8. Warning dialog from Preview is presented with the message, "The file $filename couldn't be opened because you don't have permission to view it." with subtext, "To view or change permissions, select the item in the Finder and choose File > Get Info.", and only an "OK" button.

I don't know what the right name for the underlying technology is, but the problem seems to manifest itself whenever another app asks Preview to display a file. I don't believe it's limited to PDFs, but that's what ruined my work day.

Edit: I forgot to mention, I do not experience this issue on Monterey. Issues occurred on a Late 2014 iMac that can't upgrade.

I see this too - cannot double click an attachment in Mail to open it - happened after the 11.6.6 update. It is random, and our workaround is to save the attachment to the Desktop (or a folder on the Desktop), and open it from there.

C'mon Apple - 11.6.7!!!

I just read this, submitted a bug report and I see a BigSur update for 11.6.7!

"macOS Big Sur 11.6.7 — Restart Required

macOS Big Sur 11.6.7 fixes an issue where Mail and apps, such as Microsoft Outlook, cannot open attachments if the app required to open the file is already running.

For more information on the security content of this update, see Apple security updates - Apple Support

"

I get this too on 11.6.6 but find that copying the pdfs to my desktop allows them to work ok.

Issue resolved. Apple just release 11.6.7

Hooray! Just updated to 11.6.7 mine is resolved too! - Too bad there is no way to downgrade when they release a bad apple until they get it figured out. Maybe we should be requesting that feature too.

BigSur 11.6.7 purports to fix this issue:

macOS Big Sur 11.6.7 — Restart Required

macOS Big Sur 11.6.7 fixes an issue where Mail and apps, such as Microsoft Outlook, cannot open attachments if the app required to open the file is already running.

Specifically on Outlook for MAC - I have the exact same issue (thought I was going nuts)

Tried all of the above but still no resolution - this was DEFINITELY introduced after Big Sur 16.6.6 the other day.

• PDF's won't open at all (but you can quick-look them) ... or after force-quitting Preview ... but it only works once .. then you need to force-quit again (even for the same file)
• Excel and Word attachments will open ONLY after you've given them permission once for each file access-request (i.e. after granting access in the Outlook Temp folder)

Just a royal pain in the neck !