I've been using Charles Proxy for years now but i stopped working with the iPhone simulator when I upgraded to OSX 10.9 awhile back.
I followed the directions at http://www.charlesproxy.com/documentation/faqs/ssl-connections-from-within-iphone-applications/ and when I go to execute the downloaded shell script I get this:
Error: near line 1: column sha1 is not unique
(I don't know if that is a red herring or not.)
When I connect to my server I get this back from it:
SSL: Received close_notify during handshake
Months later I actually really need to get Charles Proxy working again so I appreciate any help.
This worked for me: open the script and insert the following line
DELETE FROM "tsettings";
below the line
sqlite3 "$SQLITEDBPATH" <<EOF