Preview: New from Clipboard greyed out. Unable to annotate PDF documents.

brendafromseattle wrote:

New from Clipboard is greyed out in Preview. Cannot annotate PDF documents. Trying to capture 5 pages out of a larger document. I am using macOS Catalina version 10.15.6.

If new from clip board is greyed out— it means nothing was captured to clip board.

Some PDF will not allow you to capture, annotate, etc. depending on the authoring software, permissions etc.

Try a different PDF editor as a test, for example:

Adobe Acrobate Reader

PDFpen

pdfExpert

I don't have Catalina with me, but on Mojave, one can (with appropriate PDF permissions), copy n-tuple PDF pages to the clipboard, and retrieve them via Preview's New from clipboard menu item. From there, annotations are easy.

However, if there are any restrictions assigned to the original PDF, then these will be accompanied by password protection, and another PDF viewer (e.g. Adobe Acrobat Reader DC), or PDF Editor won't matter without that password to gain change permission and annotation privilege.