Newly introduced bug in Preview App when converting TIFFs?

I have a multi-part TIFF (4-pages) image that exports to the same number of unique PDF pages using Export… set to PDF, and the Quartz Filter set to Lightness Decrease. The PDF/A and Linear PDF are optional, but will still generate the expected PDF output.

If one has the optional ImageMagick package installed, then the following will convert the multi-part TIFF to a proper PDF from the Terminal command line:

convert multipart.tif -density 300x300 -compress zip -quality 100 mp.pdf

Apple's sips command-line tool does not handle multipart TIFF and will output a single, first-page PDF.

sips -s format pdf -s formatOptions best multipart.tif -o mp.pdf

All tested on macOS 12.1. Send direct feedback to the macOS product team responsible for Preview.

Give this a try: boot into Safe Mode according to How to use safe mode on your Mac and test to see if the problem persists. Reboot normally and test again.

NOTE: Safe Mode boot can take up to 3 - 5 minutes as it's doing the following; 

• Verifies your startup disk and attempts to repair directory issues, if needed

• Loads only required kernel extensions (prevents 3rd party kernel/extensions from loading)

• Prevents Startup Items and Login Items from opening automatically

• Disables user-installed fonts 

• Deletes font caches, kernel cache, and other system cache files

TIFFs aren't generally "paginated." They are bitmapped images which can be layered and have some metadata attributes assigned by the camera that creates them. A paginated TIFF such that it is, is really one that when printed at the resolution desired does not fit the standard page size chosen. A good layout program such as InDesign, and to some degree Adobe Acrobat DC (the paid professional edition) will manage such files better. Photoshop and Photoshop Elements can manage layers on images better than Preview. Apple's own PDF implementation is based on Adobe's open source PDF implementation at the time of the OSes production, and as such is limited by what Adobe includes. You are welcome though if you see bugs like this to report them through http://bugreporter.apple.com/ after signing up for http://developer.apple.com/ account free.

Thus hopefully if it is a feature Apple deems necessary to continue having they will have some data points to go by.

Preview is borrowing a ColorSync profile in its Quartz filter selection. Shouldn't need these with a properly working Preview, but it is a functional kludge to get that multipart TIFF properly exported to PDF. Omit that filter and you get the first page of the TIFF repeated in a PDF.

Apple does have a ColorSync Users Guide for Mac, but there is no clarification on what each Quartz filter does.

The Export… command will create unique PDF pages from that multipart TIFF image only if you use the Quartz filter as I mentioned. As a fellow user, I cannot speculate what Apple may have changed to the Export as PDF process that does not achieve the first sentence results.

I provided that feedback link so you could share that issue with the macOS product team, which might lead to a future fix.