It has done this since the day the dungeon opened, all the staff needs to do is use the serversigns plugin to add the command of /Eco give 2500 to the sign
Serversigns is a great plugin that let's you add attributes to a sign so it does things when you click it (used in parkour to gain money, heal and set home). At the moment the sign in the dungeon one has 2 attributes attached to it. One is the /mbc command which used to broadcast in shout that you'd won the prize (has been blocked by using a world guard [hence the message Jaruv got]) and the second attribute is the cool down to the sign (I believe its 6 days or so)
To add the pay attribute to it (thus fixing this problem) you would need to execute the command '/svs add /eco give 2500'
Then hit the sign.
The '' part of it means the command (once clicked) will be from the console
The '' part of it means it will replace '' with the player's name whom is hitting it
If you want more info on this easy fix go to
http://dev.bukkit.org/bukkit-plugins/serversigns/