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I have recently tried PuDB, and, I have to say, it is pretty damn nice. Never again will I use pdb/ipdb for debugging, now I can actually debug like a human being!
I have had some success using winpdb. it allows for graphical full screen debugging and it also allows for remotely debugging.

this allows me to set up the debugger in some code on my dev box and run winpdb on my own box.

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Pudb depends on the "termios" module (POSIX style tty control), whose doc says it's only available under Unix.[1] Does anyone know if there's a way to make it run on Windows (native Windows command prompt, not Cygwin)?

[1] http://docs.python.org/2/library/termios.html

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It's unclear why you'd want to do so, since the Windows console environment sucks. Just use Winpdb, pdb, your Python IDE or whatever.
Or ssh (putty or your favorite windows ssh) into a vagrant box and use PuDB or whatever you like.

I'm beginning to see vagrant as cygwin's competition. Not quite a killer, because you can't run windows progs from vagrant/linux like you can from cygwin, but for most cygwin scenarios vagrant with a real *nix is much nicer.

Best of both worlds, ssh into vagrant from cygwin.

Or you can run Linux in a VM for CLI goodness. Better yet, run Windows in a VM for security goodness.
WHY is easy_install still used?
Cant wait to try this out in my workflow, but I really wish this was available through PIP. PDB has served me well, but having some if this information intuitively shown will be incredibly helpful.
I just installed this using pip. Is PIP something other than regular old pip?
It is available though pip.
Just tried this out, and I must say, this is really freakin' cool! Simple controls, intuitive layout. I don't feel like I'm fighting the debugger to get it do to what I want anymore.
I think the "Curses"[1] section in the Unix Hater's Handbook[2] applies well[3] here[3] :)

[1] A reference to ncurses.

[2] The book: http://web.mit.edu/~simsong/www/ugh.pdf

[3] ... as in why make a UI for a constrained primitive interface such as a console....

So I can use it over SSH... which I do often. It's not like curses apps are that hard to make, especially with Python.
I read the UHH many years ago, and learned a lot of useful information from it. It's a wee bit dated, but still a fun read.
It's amazing how so much of it is still so so relevant today!

(The book was published in 1994.)

That's not amazing, that's just sad.
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"Curses" actually refers to "curses". "ncurses" is new curses. From Wikipedia:

“[…] ncurses is a free software emulation (clone) of the System V Release 4.0 (SVr4) curses, which was itself an enhancement over the discontinued classic 4.4 BSD curses.”

How is this better than pdb + emacs?
Do you have any magic sauce in your emacs config for python debugging or just the standard?
If it's a console app... isn't the full-screen bit up to me?
"full-screen" as in "fills your console instead of scrolling" not "makes your console fill your monitor".