Why can I no longer insert a document in a file? Macbook pro

Hi cherim4,

Are you specifically trying to insert a file or page into a PDF or is this a different file type?

• Add, delete, or move PDF pages in Preview on Mac - Apple Support

If you're being prompted for a password, it is possible the PDF was already password protected or a password was added to it. For example in Preview you can password protect a document. This is a completely self contained password, it wouldn't necessarily be your login password or Apple ID password.

We'd recommend confirming if you recall taking these steps when working with the document in Preview:

• Password-protect a PDF in Preview on Mac - Apple Support

"Set a password for opening, printing, or changing a PDF

1. In the Preview app  on your Mac, open a PDF.
2. Choose File > Export.
3. If you want to create a password-protected copy and keep the original PDF unencrypted, enter a new name for the PDF.
4. Click the Permissions button, then do any of the following:

• Set a password for opening the PDF: Select Require Password To Open Document. Enter a password, then retype it to verify.
• Set permissions: Select the checkbox next to an action to allow printing or changes without the owner password. Leave the checkbox unselected to require the owner password.

1. Enter a password in the Owner Password section, then retype it to verify. It can be the same as or different from any password you created in step 3.
2. Click Apply, then click Save.

Changes take effect the next time the PDF is opened."

Cheers!

Hi cherim4,

If a password is being asked, this is typically referring to one that was created on the file. If these are personal files as you mentioned with never having put in a password, we would recommend contacting Apple Support so this can be further investigated as this is not expected behavior.

Thanks for using Apple Support Communities.