This is my first attempt at creating an additional glyph for the Ubuntu Font Family. I was checking out this bug report and decided to create the missing glyph.
Any typophiles out there? Which is the best approach to design a German Capital Sharp S (ẞ)? I will tweak it futher as time permits, following your suggestions. I have just started!

would be nice if you could show some more examples of it context,
makes it easier to decide if it fits the rest of the font well
for the letter alone the angle of the “cutoff” at the end, in comparission to the angle of the inner middle part of the “3” seems a bit off
or maybe more likely that the angle of the “3”-bit needs some more tweaking
just a hunch, would need to play with it for a bit to verify which one – if anything
nice work, german gravestonemakers will be delighted
That is Windows sir, not Ubuntu
My advice would be to set it inside normal text with latin characters in several large display sizes as well as small body text sizes, with variations so you can see how it looks in an all-caps situation, etc. I would also recommend to print this specimen out as a printer’s resolution allows you to spot problems much more easily.
Also most font editors have an option to display a type specimen upside down and mirrored which helps a _lot_ when you’re fiddling with kerning amounts.
I looked right now around the ubuntu blogs and planets for a document describing the style of Ubuntu Font glyphs and the principles and decisions behind them, but found nothing but “The four Latin characters, ‘n o H O’ helped to define a guide for around 80-percent of the remaining characters.”
Well, my general approach is to try some words, placing them in appropriate scenes and stare at them
ẞ will only appear in all capital words, often logos. Examples are STRAẞE, GRUẞ, GRÜẞE, ANDERẞEN (saw that as a logo of an expensive garment store, with an non-specialized ß; looked arkward), FUẞBALL, FLEIẞARBEIT. Looking at these examples right now, the Arial ẞ in Fedora Firefox suffers from bad hinting. Bold and fuzzy. An appropriate scene would be as a replacement for the ubuntu logo (at boot, at ubuntu.com) or in other logos.
Also the combination of “fs” could inspire http://de.wikipedia.org/w/index.php?title=Datei:Sz_modern.svg&filetimestamp=20070825090708
Also ẞ is called “sz”, the “z” brings the sharpness, and a straight diagonal connecting the upper right to the bulb below, would also be interessting.
Also I want to use strong words against your use of Times New Roman and Arial, besides using Vollkorn for headlines.
Hehe, I know, but that’s what this WordPress theme uses :/
I think you’ve got the terminology wrong. It’s not a sharp S, and it’s not an sz. It’s the long-s short-s ligature. It’s the ligature of this: ſs.
And just doing one ligature is of course not enough if I want to write with ligatures, I want all of them. st Æ, æ, Œ, œ, IJ, ij, ᵫ, ff, fi, fl, ffi, ffl, ſt. And this one of course: ſ. I mean, having the ligature but not the originating character is kinda pointless.
The sharp S might have originated as a ligature, but now it’s an independent letter.
Interesting work! I think it is hard to say much more without giving the glyph more context.
Personally, I like the ẞ variant which is not rounded in the upper left, but has an 90° angle (like http://upload.wikimedia.org/wikipedia/commons/6/6b/P22underground-bold%C3%9F.png), but I think it has to work with the existing glyphs and often that variant doesn’t fit into existing fonts.
You have chosen a model of ß where the right part looks like the digit “3″. I think that is a not a good decision, given that this is not the model of Ubuntu’s small letter “ß”. A well-designed font should not use different models for small and capital variants of ß.
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> Which is the best approach to design a German Capital Sharp S (ẞ)?
See http://opentype.info/blog/2011/08/03/how-to-draw-a-capital-sharp-s/
Proponents of ẞ rarely like forms such as the one proposed above, for two reasons: (1) it too closely resembles B, and (2) it too closely resembles the lower-case ß. It’s better than nothing, of course.