Black Boxes and Bad Habits

I had to chuckle when I read this Verge article about Meta’s attorneys botching their document redactions during the FTC antitrust trial. Having spent three decades in the legal racket, it was shocking to me how often lawyers (and their staff) were completely flummoxed by the idea of digital redaction. Way more often than not, someone would just draw a black square on top of a PDF and send it to me, blissfully unaware that all the underlying text was still there, searchable, and easily extracted.

You’d think that by now they’d at least teach how to avoid this potential act of malpractice in law school. But alas, it appears they do not.

The funny part is, this isn’t even hard anymore. There are any number of PDF tools on the market today that will properly redact a document and permanently remove the underlying text. But time and again, we see these same mistakes, often in high-profile, high-stakes cases.

It’s easy to make fun of this stuff (and I do), but someday it might not be Apple’s secrets showing through a bad redaction job. It could just as easily be your Social Security number under one of those black boxes.

The legal profession has a complicated relationship with technology. Some lawyers are very tuned in, using tech to get real leverage in their practices. Others act like technology doesn’t exist at all, hoping to retire before it becomes their problem. Incidents like this show that the problem is already here, and pretending otherwise doesn’t help.

Discover the New PDF Fill-in Feature in macOS Sonoma (MacSparky Labs)

Filling in PDF forms just got a lot easier on the Mac. This new feature reliably and quickly adds fill-in fields to your PDFs in Preview and Apple Notes.…

This is a post for MacSparky Labs Level 3 (Early Access) and Level 2 (Backstage) Members only. Care to join? Or perhaps do you need to sign in?

Save as PDF… (Revisited)

Apple made some more changes with macOS Ventura that broke my “Save as PDF…” workflow.

Here’s a video explaining what changed and how to fix it. If you’ve never tried this trick, you should. It really speeds up the process of making PDFs on your Mac.

Automating PDF Creation from Image Files on the Mac


Recently a client sent me a contract electronically by taking a series of photos of a document. This happens to me once in a while, and usually I open the individual images in Preview, combine them, and save them as PDF. I received another such series of photos this morning and finally decided to automate this process so I don’t have to do it manually anymore. Automator to the rescue.

Why I Love Automator Services

Automator has the ability to create Services. These are little programs that reside in the contextual menu on your Mac. Right-clicking on a file gives you an option to employ Services. The nice thing about Services is that they stay out of the way until you need them, and then they are there, just a right-click away. (All screenshots in this post will get bigger on your screen if you click them.)



So I decided to make my little automation routine for combining PDF files a Service. This happens after you open the Automator App and click New in the File menu. 



In order to get to the Services menu, you’ve already selected a file. This means the Services don’t need the typical file-selection nonsense. To run the Service, you’ll first select the images you want to combine and convert to PDF. Clever, right?

Because the Service we are creating is made specifically to turn images into PDFs, we don’t want our Macs to try and use it against other types of files such as text files or music files. Therefore, we will limit the Service so that it only works when it receives image files.

Now Let’s Get Automating 

If you’ve never used Automator before, don’t sweat it. It’s easy. Automator has a series of tools on the left side that you drag into your workflow on the right side. You stack those together like LEGO bricks and at the end you’ve created a program. This Automator workflow has just two bricks. The first thing we’ll need to do is take the existing images and convert them into a single PDF.



Fortunately, Automator has a tool specifically for this job named, not surprisingly, “New PDF From Images”. Go in the Search bar for Automator and type “new PDF”, and the search gets you there. 



Drag the tool into the workflow area and we’re halfway there.



The Quartz Filter

We could really stop with just the one step and convert the images to PDF, but there is still a problem. Photos converted to PDF still make lousy documents. They have lots of color and are hard to read. 

MacOS has quartz filters built in that can change the way a PDF looks. There’s also an Automator tool to apply a quartz filter right in your workflow. So go ahead and search for “quartz”.



Drag the “Apply Quartz Filter to PDF Documents” tool into the workflow. When you do that, however, you’ll get the following dialog.



This dialogue is Automator being extra careful that you don’t override something you want to keep. For this workflow, I clicked “Don’t Add”.

After that, you’ll see the workflow with both steps.



You’ll note in the above screenshot that the quartz filter isn’t doing anything yet. Time to change that. Click on the arrow next to the filter and select “Black & White”. This converts the color image to a black-and-white image and makes the document much easier to read and edit.



That’s it. Save the script, select some images, right-click on them, and try it out from your Services menu.