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I've written my own analogue of OpenSSH's ssh-askpass. At the moment, it's contained inside Pageant proper, though it could easily be compiled into a standalone binary as well or instead. Unlike OpenSSH's version, I don't use a GTK edit box; instead I just process key events myself and append them to a buffer. The big advantage of doing this is that I can arrange for ^W and ^U to function as they do in terminal line editing, i.e. delete a word or delete the whole line. ^W in particular is really valuable when typing a multiple-word passphrase unseen. If you feel yourself making the kind of typo in which you're not sure if you pressed six keys or just five, you can hit ^W and restart just that word, without either having to go right back to the beginning or carry on and see if you feel lucky. A delete-word function would of course be an information leak in even an obscured edit box (displaying a blob per character), so instead I give a visual acknowledgment of keypresses by a more ad-hoc means: I display three lights in the box, and every meaningful keypress turns off the currently active one and instead turns on a randomly selected one of the others. (So the lit light doesn't even indicate _mod 3_ how many keys have been pressed.)