The principal reason is that the form is named frm in the calling code:
Dim frm As New BOSForm
but you have referred to it as BOSForm in the form code, and as that doesn't effectively exist, the code is ignored.

Your userform doesn't display the check box fully, and it has no cancel button. Both are addressed in the attached.

I was puzzled how you were able to use content controls in a DOC format document, until I checked and found that this is a DOCM format document with the extension renamed as DOC. There is no good reason (apart from enabling it to be attached to a message in this forum) to do this and it can cause problems, so use the correct extension (and use zip to attach it).

The attached does create the PDF.

Attached Files

FOR POSTING.zip (34.9 KB, 17 views)

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Graham Mayor - MS MVP (Word) (2002-2019)
Visit my web site for more programming tips and ready made processes www.gmayor.com