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Here is my 2 cents on this issue.
I am attaching a group of 3 macros which might help a bit.
Let's assume you have one drop cap in your document already. Place your cursor in a subsequent paragraph where you want another. Then run the first macro: Insert DropCap At Current Paragraph
This macro will copy the first drop cap in your document to your current paragraph and replace the letter with the current initial. It will also leave the floating text box selected, so you can adjust the location with the cursor keys.
The other two macros can be used to widen and narrow the selected text box to adjust for wider/narrower letters. They will adjust the box by +/- 2 pts at a time.

I was thinking that another strategy might work. If you use a standard font and size for the drop caps then the insert macro could be made to adjust the width of the box immediately to accommodate the letter. One would have to create a rough list of widths for different letters first. If you have such a list let me know and I can adjust the macro accordingly.

NOTE: I am using a text box anchored to the paragraph of course. Copying this worked for me, and placed the drop cap in roughly the correct location.

These worked for me as advertised! Thank you a lot. I did have some peculiar results, however.

I inserted Drop Caps in 11 paragraphs in a document, one every two pages or so. the last one, I started getting spinning rainbows that lasted 30 seconds or so. Then, with the document sitting idle (at least I wasn't doing further editing), the drop cap for paragraph 11 suddenly jumped into the middle of paragraph 10 a couple pages earlier. I wasn't able to get the doc to scroll to see what happened in other instances. Eventually, I resorted to recovering an earlier version of the document and deleted the one with drop caps.

I may do some further experiments with the macros, ideally with only Nisus Writer Pro active, if I have time. (I had a dozen other apps open but idle.) If I do, I'll post an update.

I'm sorry that you had such trouble. If you can save a document with problems like that you might want to share it (Perhaps with Nisus using the feedback button. Tell them I sent you )

I just tried a very simple test: 10 Pages of copied text. I randomly inserted 17 Drop Caps without a hitch.

My suspicion would be: Other open apps are not likely to be having any effect. Probably your document is a more realistic test than mine, with more complex formatting and more complex pagination, by which I mean formatting which forces Nisus to calculate layout, etc. Since these drop caps are floating content, they require Nisus to do complex calculations when such an item is near a potential page break. You may be able to improve the situation by strategically inserting hard page breaks at certain places in your document.

If you do get around to giving another test, save after every couple of drop caps and/or try saving, closing and reopening the document as you go along.

G'day, all

It's important to be aware that text within a Text Box is not considered as a substring of any "adjacent" string when it comes to Find & Replace. This means that a whole word with one or more initial characters displayed as drop caps by means of a graphic device will not be found in a search.

For this and other reasons, it would really be nice for drop caps to be implemented more deeply within the application, with due regard to font metrics.

After Brad's mention of Pages (which I hardly ever use), I had a quick look at it. It appears to have quite a nice implementation of drop caps which does admit of conventional text searching.

Cheers,
Adrian