PDF woes — PDF Expert and Preview too tolerant?

I’m curious whether anybody else has encountered this issue and if they have any proposed fixes.

The challenge:

Our local courts now require exhibits for hearings to be submitted as a single .pdf with a linked index at the beginning and bookmarks for each exhibit. (This is great—I encourage more sophisticated legal documents!)

The problem:

This afternoon, I used PDF Expert on my Mac to put together just such a submission. Everything looks great in PDF Expert, everything works as expected in Preview. But, as soon as I email it to anybody on Windows or upload it to the court, the whole .pdf fails to work.

After investigation, it turns out the problem is that some of the component .pdfs had e-signatures. Acrobat doesn’t like you to modify those .pdfs and so it was corrupting the whole document. I had to strip out the offending .pdfs. Create versions without the security features (by printing to Preview and then Exporting as PDF using Preview).

I don’t mind having to take extra steps to strip out e-signature information. I’m more concerned that neither PDF Expert nor Preview provided any notice that there was a potential error.

I’m left to wonder what to do going forward. Do I, effectively, have to subscribe t o Acrobat to avoid this? Or would PDFPen Pro have faired better? Or is there some way to set PDF Expert or Preview to “strict” mode so that they are very conservative in what they will open/export?

Any thoughts appreciated.

I don’t know the technical answer, but for my own work I use the tools my clients and business associates use. It’s a reasonable business expense that avoids incompatibility issues, or at least reduces them and makes diagnosis easier.


Could you use the free Acrobat reader to test how/if it opens?

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It’s like working with people who use Microsoft Word. Lots of apps can create .doc or .docx files. Lots of apps can read .doc or .docx files. But the only app that does it exactly the same way Microsoft Word does it, is Microsoft Word.

Theoretically, PDFs should be different (hence the P in PDF).

In practice, Acrobat does what is considered standard and anything that doesn’t meet that standard will be considered “broken”.

Yes, it sucks that Adobe can basically charge whatever it wants, and their prices are nowhere near as friendly as what Microsoft charges for 365. But unfortunately I think your best option is just to pay it as a cost of doing business, like electricity and Internet.

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Are you confident the free Acrobat Reader won’t suffice?

Yes, because the question is about creating PDFs, not just viewing them.

I had been using PDF Pen, PDF Expert and Preview for 14 years.

Last year, I switched to the Adobe Creative cloud. I already was using Adobe’s Photography plan. Being an Adobe Acrobat user at work and given the constant issues with other apps (almost as good as Adobe Acrobat is not the same) I jumped onto Adobe’s Black Friday offer for charity (EDU): I pay 15 Euro per month for all of their apps. If I recall correctly, it will increase to 19 Euros in the fall. Well worth it to me. If I add up all of those app subscriptions or licenses that need to be bought for alternative software I had been using before, I am almost at that price point.

That is not the solution for everyone. My suggestion would be to use Preview. It does a lot more than one might expect seeing it at first glance. If not, PDF Expert and PDF Pen are ok alternatives. Both of them have their individual strengths and weaknesses. If you know Adobe and if you are eligible for EDU pricing, it might be an option to just use it instead of constantly struggling with issues other vendors have…

I also have to work a lot with Windows users and always use Acrobat to create PDFs when I’m know it needs to be cross platform. Luckily my institution provides a license.

I’ve tried using both PDF Expert and PDFpen and both made PDFs that had compatibility issues with Windows. Commenting PDFs (which I do all the time) was particularly problematic. With Acrobat it works 100% of the time.

May I ask how you created the Index at the front of the pdf? I was not aware one could do that with any of PDF Expert, Preview or Acrobat DC.

I have found, however, PDFSAM.org, the free version of which includes a merge function that will combine multiple pdfs into one, with the capacity of both bookmarking and an index.

Unfortunately, one cannot edit the Table of contents page much.

Sorry, I thought the need was to “test” the PDFs re: the end users’ experience after they were created.

Perhaps you should try to fix the problem with signatures first. Create the document without the index and bookmarks by saving the PDF as a flattened version. Then create the index and bookmarks.

In the meantime, at some point, you will likely have to get the Acrobat Pro version and be done with it.


Thank you all.

My issue was with neither Preview nor PDF Expert alerting me to the apparent problem with the .pdf I created in PDF Expert. I’ve now tried creating the same .pdf with PDFPen Pro, and it does a good job of flagging the issue with the signatures during creation.

If I don’t want to subscript to Acrobat Pro (and I don’t), @Jezmund_Berserker probably has the right idea—of at least using Acrobat to test PDFs created with another tool. Based on this experience, I think that tool will be PDFPen Pro.

Nothing fancy. I just created a .docx in Word that included our case caption and an index listing the exhibits with a description of each. I saved this as a .pdf and then (using PDF Expert) combined it with the various exhibits into a single .pdf. I then added the bookmarks, and linked the text in the index to the first page of each exhibit.

The process was fine except that PDF Expert didn’t throw an error when I combined e-signed pdfs into the larger, combined .pdf. Attempting the same thing in Acrobat or PDF Pen results in an error, forcing me to (correctly) flatten the e-signatures first.

The process in Acrobat is virtually identical.

A while back, I submitted an arbitration exhibit packet with a table of contents and bookmarks, but I can’t remember whether I used Preview or PDF Expert to build it. Whichever one I used, I had a similar experience to yours. I remember testing it in Adobe Reader before sending it out, and it wouldn’t open. I also can’t remember how I fixed it, but I didn’t purchase the Adobe subscription so I can rule that one out.


Yes, I have created the table of contents that way in Acrobat DC too. Rather time consuming! But at least you can set up the cover page with the headings etc. as you like.

PDFSam.org does it much quicker. Give the merge module a try.