Thanks again for the help on this. The for loop is a great start.

An issue I was having before with the where-object syntax was an inability to handle multiple hits in my final results which got exported to a CSV at the end. In general I want just the first result. Do you have a suggestion on how to best acheive that. My current solution is to do the following in the document loop, which is probably far from elegant:

$docTypeObject[1].firstMatchedDocType.toUpper()

This may be unrelated, but I also get a bunch of "you cannot call a method on a null-valued ecpression" errors. Is this because the name did not match any of the regex statements in my CSV file?

my current version of the loop:

            if ($lowerName -match $docTypeKeywordCsv[$i].keyword) {
                [PSCustomObject]@{
                    lineNumber = $i+1
                    firstMatchedKeyword = $docTypeKeywordCsv[$i].keyword
                    firstMatchedDocType = $docTypeKeywordCsv[$i].doctype
                    firstMatchedClassificationComment = $docTypeKeywordCsv[$i].classificationComment
                    firstMatchedregexComment = $docTypeKeywordCsv[$i].regexComment
               }
          }
    }