Create PDF Portfolio from Outlook email

To add more clarity on the problem, I created some screenshots to illustrate my relatively simple process. Please forgive the redactions and on-line blurriness.

Create PDF Portfolio from Outlook email

I've done this task successfully dozens of times before (maybe in the hundreds), but it's not working anymore. I've sometimes had issues in the past I've been able to fix. Not anymore.

I want/need to create a PDF Portfolio from a specific batch of Outlook emails.

Here is a redacted example of what a PDF Portfolio looks like:

My steps:

Starting within Outlook, I choose "Search" to generate a list of emails I want in the Portfolio.

I then highlight/select all the emails in that batch.  I right click within that list, then choose “Convert to PDF” to convert this batch of emails to an Acrobat PDF Portfolio.

A pop-up window "Save Adobe PDF As" appears (see below).  Here is where the process seems to break down: it seems like Microsoft Outlook and Acrobat Pro are not communicating with each other.  I can tell at this point the task has failed based on the suggested “File name.”  If it suggests a name for the Portfolio from the subject line of an email, it failed. Rather than creating a PDF of all the emails I selected, it will PDF only that one email, even if its not one that I selected.

Below on the right, you’ll see my search criteria and search results—the email batch I want in the PDF Portfolio. On the left is the Outlook inbox. Rather than focusing on (or calling) the list I created, the Convert to PDF “function” has reverted back to the top email in the email box which is not one that is in my selected list.

Ultimately, only 1 email end up in this PDF portfolio, and it’s not one that was in the selected batch:

I'm using Acrobat Pro 2020 and Microsoft 365 Outlook. I've tried the trick of unchecking/rechecking the box for the Acrobat PDFMaker add-in (as suggested by another post here).

I tried uninstalling & reinstalling Acrobat Pro (which was a mess that I will never do again). I chatted with Adobe Tech Support who tried to help me (including running repairs to both Acrobat and Office), but ultimately blamed it on Office and said I needed to contact Microsoft.

 I chatted with Microsoft, but they said that Acrobat created the Add-In and Microsoft doesn't provide support for 3rd party apps.

I again tried to get help from Adobe, but after I showed then tech in chat the issue, he just disconnected without helping me.  That happened twice--they can get away with that??

Please help!

I'm considering looking at another software package that claims to be able to successfully create these. If so, maybe we switch abandon Acrobat Pro altogether.