@ Meagan
RE: I’m importing the directory listings for each category as a CSV file.
You should use the CSV Import addon to import entries, not the bulk Category Import tool.
The bulk Category import tool only imports categories, nothing else … it can not associated imported categories to entries, for example.
RE: I originally used the CSV import option but each of the categories have hundreds of listings. If I use CSV import I am having to open each entry and manually update the category ID which will take lots of time with hundreds of entries.
If I understand correctly… when the entries were imported, they were not imported with their assigned categories. Is that correct? And now you wish add those category associations to the imported entries?
Probably the easiest solution is to export the entries using the Export All tool found on the Connections : Tools admin page under the Export tab at the bottom.
You would then edit the exported file to include the the categories that each entry should be assigned to. Then import that modified CSV file.
If I recall correctly, the import should update the existing entries with the associations to the categories.
I recommend doing a test import of only a row or two to verify if you get the desired result or not.
Hope this helps!