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On macOS Monterey, v. 12.5, MacBook Air M1, 2020, and the latest version of Word for Mac (v. 16.64 (22081401), you have two options.

If your .pdf is text based, and the God's pity you, you'll have no issue converting the document into text. But what half decent lawyer wants to do that when having to assert to the authenticity of an exhibit, right?

So you're going to need the actual pages of the document. You can easily insert (secondary click > insert picture > boom!) a .pdf no matter how many pages it has, in fact, when the file choosing window comes up, you even get to use the left-right arrows to have a glimpse of the page of the .pdf. But for what end!? Because even when you turn the pages to one you wanted, but the first page, it will still enter, but the very first page.

In that very window, there is a button labeled "Option", and there is something alluding to some "range[s]", but even there you cannot define which one or more pages you needed let alone ranges or pages and ranges you needed from a file. Íf you choose the file, it defaults to inserting page one.

The work around is 1. separating the .pdf into (at times hundreds) of individual files, and pumping them into Word one by one. This is laborious and wasting ridiculous amounts of times in bigger litigations of costly billable hours even if you had the privilege to have paralegals do it for you as a fresh out the bar sole practitioner.

So, yeah, someone please help.

If nothing else, how can you batch insert all the pages of a .pdf even if you can't pre-specify which ones you needed (you can still then quickly select them with the mouse, and delete what you don't need)?

Bonus, how would it be possible, if at all, to select different non-continuous ranges of pages of a single file to squeeze in. (If you answered the first, that will probably green mark the answer with full satisfaction.)

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I don't think Word has the ability to insert or import multi-page PDFs.

However, you can automate the process of splitting the PDF into single files; and a quick test shows that selecting several single-page files (with sequential filenames) and dropping them all on a Word document will place each one consecutively into the document.

There are utilities that will automatically split pages of PDFs into separate files, each indexed by page number. These include apps like Adobe Acrobat, PDFPen Pro, PDFMaster (all paid-for); and PDFSam (free).

There is even a Split PDF action in Automator and Shortcuts.app that you could use to create a Quick Action in the Finder.

There are other scripting methods of splitting PDFs, but these involve installing additional command-line software, like GhostScript or python.

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  • We're talking about ~150, a good 6-7 pages avg., the reason why the individual files are, other than with some automation, are out of question
    – Kortelly Zamatosh
    Commented Aug 30, 2022 at 9:39
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    @KortellyZamatosh I don't understand your first sentence about questions. Are you saying you want some help constructing a workflow with Shortcuts?
    – benwiggy
    Commented Aug 30, 2022 at 9:47
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    @KortellyZamatosh Also, would it be easier to combine PDFs (including of the Word document elements) together, instead of combining things in Word, which is not suited for the job?
    – benwiggy
    Commented Aug 30, 2022 at 9:48
  • the issue with combining the documents is that in Word you can dynamically (to some very limited and fail-prone manner) automatically update exhibits signall, like "Exhibit F" can turn into "Exhibit G" should another exhibit be entered in the document prior to the location of F later. That's why it's import to do it there. Although, it's limitations are clear. Once you enter many, Word can substantially slow down on portable machines.
    – Kortelly Zamatosh
    Commented Aug 31, 2022 at 17:41
  • Would it be possible to write a Word script so that the multi-page .pdf issue itself could be addressed? Like, pull in all .pdf's from a folder where you previously put each page of a document in page-order.
    – Kortelly Zamatosh
    Commented Aug 31, 2022 at 17:43

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