6. Paste in Word -> the image is missing.
The reason behind the missing image is, as I believe, based in the fact that Word remembers its own objects of what it put into the clipboard, and then, when it performs a Paste operation, it doesn't read the actual contents back from the Clipboard, but instead tries to use its own cached objects - which may be discarded at that point (due to another Copy operation, overwriting the previously cached data).
If you only record and restore plain text, then this won't be an issue, though.
Only if you try to record more complex data, such as images with text, or advanced (Word-specific) formatting, this becomes an issue.
I can think of several ways to resolve this:
1. Office could read back the image it put into the clipboard's RTF type, by supporting Apple'd rtfd format.
This would have the advantage that it could solve another issue Mac users currently have: Copied text+images are not transferable from Word to non-MS apps, such as TextEdit and Mail. The reason behind this is that Apple uses their own (rather private) rtfd format to embed images, which Office code doesn't support by default, as their have their own way of embedding images into RTF (but which Apple's RTF reader doesn't support - which, ideally, Apple should fix).
A few years ago, it even didn't work in either direction, but it seems that recently MS added the ability to understand Apple's rtfd format, at least. Now, we need to get MS to also _created_ rtfd bundles on macOS. It's not that difficult, and maybe we can assist them. It would not only help us Clipboard tools makers, but practically every Mac user who wants to copy text+images from Word into other apps outside Office.
2. Office could place more information into the pasteboard so that all the information for restoring the objects later would be present. Currently, it seems that Word only puts a reference to the internal objects into the clipboard, but not the object's contents. This is probably done for performance reasons, but there are ways to resolve this (e.g. with delivering the data on-demand). This might be easier to implement for MS, as it would use private types that Office can read back without much work (as long as they can be serialized), and it would have the advantage of preserving all the intricate formatting that would get lost when converting it all into RTFd and back.
3. Ideally, MS would do both.
What do others think? Can I get your support?
Please no nay-saying in the form of "they won't listen to us", because I've been in contact with some MS devs in the past, and were listening. But there's always priorities getting in the way, and so we need to convince them that this is (a) actually helping enough customers to make this effort worthwhile and (b) we're happy to assist them.
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Thomas Tempelmann
Irradiated Software