Problem converting .tif files to .pdf files in groups

Hello, 


Recently I scanned an old diary of a family that are friends of ours, using an Epson V600 and Epson Scan 2 (which normally I use SilverFast 6 while I was on my M1 MacBook Air but I had a problem with the software so I used the default Epson Scan software sometime after getting my M3 MacBook. However that issue is my fault alone and neither the software nor Mac), and have all the scans saved in a .tif file format. 


What I normally do is save the files in .tif format, then go to the first .tif file, click the dropdown for Thumbnails, and then drop in the rest of the .tif files, select all, File, Export (because I don't want to Export as PDF to get the scan on a white background), change the settings to export as PDF. Then I combine all the pdf files together to create one pdf for the whole document, diary, etc etc etc. 


However now when I do that, when the selected exported tif files are turned into pdfs, only the first file actually works, and the rest don't work and don't have a thumbnail. Whenever I click on those screwed up ones it says: 


Impossible to open the file « imagefilename.pdf ».

It might be damaged or in a format not known to Preview. 


However whenever I export as pdf those same tif files individually, they all come out just fine. 


Thats why I think that this is an apple software issue and not of the scanning software.


I have a 2024 MacBook Air M3, macOS Sonoma 14.5 (was on 14.3 but updated to see if they fixed it but they didn't so far)

MacBook Air 13″, macOS 14.5

Posted on Jul 27, 2024 5:59 AM

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Posted on Jul 27, 2024 6:42 AM

You could use the command line tiffutil tool to concatenate all .tif files to a single output .tif and then use Apple's command line sips tool to produce a PDF. I haven't tried this with n-tuple .tif images and it may or may not be a solution for you.


In the Terminal application, change the directory to the location of your scanned .tif images.


man tiffutil
/usr/bin/tiffutil -cat 1.tif 2.tif 3.tif ... n.tif -out final.tif
man sips
/usr/bin/sips -s format pdf -o final.pdf final.tif


8 replies
Question marked as Top-ranking reply

Jul 27, 2024 6:42 AM in response to PSidle

You could use the command line tiffutil tool to concatenate all .tif files to a single output .tif and then use Apple's command line sips tool to produce a PDF. I haven't tried this with n-tuple .tif images and it may or may not be a solution for you.


In the Terminal application, change the directory to the location of your scanned .tif images.


man tiffutil
/usr/bin/tiffutil -cat 1.tif 2.tif 3.tif ... n.tif -out final.tif
man sips
/usr/bin/sips -s format pdf -o final.pdf final.tif


Jul 28, 2024 8:18 AM in response to VikingOSX

VikingOSX wrote:

Note that in Sonoma 14.5, exporting a 6-page TIFF to PDF from Preview results in a single, 6-page PDF.

This bug happens with individual images in Sonoma:


...opening several .tif files to Preview.app's thumbnail sidebar > Select all > Export Selected Images > Format PDF:


...exports the 1st as .pdf as desired, but the others have .pdf suffix but are really .tif files.


A similar bug happens when exporting .raw (.cr2, .cr3, .dng) files as .jpg: only the 1st is exported as .jpg, but the others have .jpeg suffix but are really .tif files.

Jul 28, 2024 9:46 AM in response to VikingOSX

VikingOSX wrote:

Concerning the opening of several TIFF images in Preview and using the export selected to PDF, I found that some with a resulting PDF extension are just that, and others bear the Preview icon and remain TIFF images with PDF extensions. Five of the seven TIFF images became real PDFs and two remained TIFF. D'oh.


I guess the reason why some input files behave like this is that APFS file system feeds files in some randomish pattern to be processed.


In my test I tried to bypass that by carefully one-by-one choose each input .tif file in the Finder before opening them all in Preview.app because otherwise they were put in random order in its thumbnail sidebar.


This is why exiftool needs '-fileOrder5 FileName' option to put the input files in order in some commands. MacOS Extended does need this.

Jul 28, 2024 9:26 AM in response to Matti Haveri

I tested this with a multi-page .tif image, not individual .tif images.


Concerning the opening of several TIFF images in Preview and using the export selected to PDF, I found that some with a resulting PDF extension are just that, and others bear the Preview icon and remain TIFF images with PDF extensions. Five of the seven TIFF images became real PDFs and two remained TIFF. D'oh.

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Problem converting .tif files to .pdf files in groups

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