Is it possible to save an image that was annotated in Preview as a PDF file so I can edit it again later, even after restarting Preview?
MacOS – Save an image (PNG) with annotations as a PDF
macospdfpreview
Related Solutions
This works for me on Mountain Lion:
Open all the JPG's in Preview so that the files are selectable within the one window, i.e. thumbnails of the JPG's are viewable in the selection pane located the window's left side.
Click in the selection pane and select all the thumbnails with Cmd-A.
Select File > Print... from the menu bar.
Select PDF > (from the drop down) Save as PDF... from within the Print Dialog.
Take it from there...
I've run into this with some forms, it's not always clear why (although in your case the DRM seems the likely culprit). The workaround for me has always been filling it out as normal, then using the print to PDF functionality (File → Print → PDF → Save as PDF). Certainly not the easiest, and it means you can't re-edit in some situations. But it's still better than dealing with Acrobat.
Alternatively, you could buy PDFPen, which is a pretty fool-proof way of dealing with any PDF form you can find.
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Best Answer
You can always use File > "Export as PDF…" or even File > Print… > click PDF options in lower-left corner as a way to convert anything open in Preview to PDF. However, any annotations made to an image format such as PNG without converting will be flattened/rasterized when saved or converted to PDF and can't be edited. You will need to first convert the image to PDF then annotate in order to be able to edit annotations later.