I am stumped by this problem, which probably has nothing to do specifically with winpdb. To get winpdb to the current version I wound up installing and uninstalling several times. It now works, but I can't start it using the command "winpdb", even though it is on my path. And I get "No such file or directory" rather than "command not found" even if I'm the directory where it lives. However, when I'm in that directory, I can run it with ./winpdb. This [https://askubuntu.com/questions/133389/no-such-file-or-directory-but-the-file-exists] is the closest I've come to an answer, suggesting that it has to do with a broken symbolic link. But ls -l turns up no such link.
Here's a rundown. I used copy/paste on the cd to the full path name, so it's not just a typo. It runs at the end, and I get the next command prompt when I quit out of it:
localhost:~ nat$ winpdb
-bash: /usr/local/bin/winpdb: No such file or directory
localhost:~ nat$ nonexistentcommand
-bash: nonexistentcommand: command not found
localhost:~ nat$ cd /usr/local/bin/
localhost:bin nat$ ls -l winpdb
ls: winpdb: No such file or directory
localhost:bin nat$ echo $PATH
/usr/local/bin:/Library/Frameworks/Python.framework/Versions/2.7/bin:/usr/bin:/bin:/usr/sbin:/sbin:/usr/local/bin:/opt/X11/bin:/usr/texbin:/Users/nat/Library/android-sdk-mac_x86-1.5_r3/tools
localhost:bin nat$ cd /Library/Frameworks/Python.framework/Versions/2.7/bin
localhost:bin nat$ ls -l winpdb
-rwxr-xr-x 1 root admin 2175 Dec 31 23:54 winpdb
localhost:bin nat$ winpdb
-bash: /usr/local/bin/winpdb: No such file or directory
localhost:bin nat$ ./winpdb
localhost:bin nat$
Any help appreciated!
