Illy is particularly particular about the intrinsic quality of fonts, and that may be (part of) the problem. She may simply refuse to work with certain font(s/styles) that may be used in other applications.
You should be able to see the hopefully different appearances when you just open the (relevant) font folder from Windows, to make sure that you actually have the different styles (weights).
But here's the same text in MS Word (including a spurious cursor):
Word is an exceptionally bad choice to check this with The reason is that Word *will* make your font Bold or Italics, even if it cannot find the correct fonts! It's hard to see, though, if this has happened with your fonts.
If you select your font name in Illustrator, does the fly-out panel show all three variants?
I happen to be deep into fonts at the time; if you can send them to me I can check if the internal Bold/Italics assignments are correct.
Laura sent me the three fonts, and by using ttx to dump her files into a readable/editable format I was able to adjust them -- there were a couple of errors, probably due to the fact that FontForge didn't treat the three fonts as belonging to the same 'family':
1. the usWeightClass was 'medium' for all three, while it should be 'Bold' for just the Bold font.
2. the italicAngle in the 'post' table for Italics was 0, while it should have some negaitive value (I set it to "-12", which seems a common value )
3. a real head-scratcher, as at that point the Bold and Italics keys were working but the font menu order was still not correct (first Italic, then Regular). I finally found that for an Italic font, you should also set the caretSlopeRun and caretSlopeRise to some magic values other than the default "1,0" (indicating a 'straight up' cursor). Changing it to semi-magic (*) values "1000,176" finally solved it.
(*) Semi-magic 'cause apparently these values do something but I'll be darned if I know how to interpret them ...
Reading her original post, I belately realize I don't have Word to test it with. But her fonts pass both Adobe's 'comparefamily' and Microsoft's Font Validator family tests, so I guess that ought to be allright then.
... It was a useful exercise for me as well because figuring out that Italic problem learned me something I didn't realize could be a problem in a font!
Heh, all that time I only tested it with InDesign! Theoretically, both Illustrator and InDesign share the same type engine, but then again I got somehow convinced their respective programmers' teams Do Not Talk to each other (that could be the explanation for the myriads of little annoying differences between the two programs!).
Fortunately, there doesn't seem to be any problem -- here is Laura's handwriting in Illy.
This is wonderful! Thank you so much!
Obviously there is much I have to learn when creating and editing fonts. I think if I get around to making some more I might invest some money in a better editor that FontForge. Don't get me wrong - I'm sure FontForge is quite a capable product, but I guess it's designed for someone who already knows what they're doing!
Glad I could help!
I found the way to manually calculate the caret slope: http://www.microsoft.com/typography/developers/delivery/hinting.htm -- apparently it's the tangent of the italic angle of the font itself. I guess "usually" FontForge calculates that for you.
FontForge is a rather complete font creator package but boy! it is ugly! For that reason alone I'm not using it myself, even though it is free. And indeed you need to know lots of fonts already before you can use it to its full potential, I feel it relies a bit too heavily on your knowledge of what-value-needs-to-go-where.
The most serious font editing software is DTL's comprehensive set of tools, but it comes at a serious price as well Less expensive, and I think used by most font creators, is FontLab; they also make the easy-level starting kit Fontographer.