Well unlike u all people, I also encountered the winterboard problem and as I am a severe fan of winterboard, I felt iphone is so much boring without it, it looks so much dull…
Many places on net, it was said that winterboard doesn’t work with new iphone 3G 3.0, I encountered same problem after updating from 2.2.1 to 3.0 but I finally made out a solution and it worked fine for me, so I thought to share it with u, but I tell u something, I am a window user, very advanced rather, I have never been to MAC before (I am proud to be window user, it has more flexibility) so all I am going to tell u, is not based on some website tutorial or some knowledge. It was all based on some on and off experiences and hit and trial method techniques. But 1st I tell u what I have, so u get some knowledge:
I got a UK (O2) based phone from a friend, I am in Pakistan now. It was locked and when I got phone, it was 2.2.1 5H11 firmware 2.30.03 which is still not unlockable, as my bootloader version is 6.02 so ultimate solution was just turbo SIM or to wait for 3.0 unlocking, but finally unlocking of 3.0 came n now I am on 3.0.
So if u do as I did, u will have 3.0 without any single problem at all.
1. Update (rather restore) to 3.0 either in normal mode or DFU mode using some custom restored file.
2. If u r not running a legitimate sim card, u gona have a lock screen with emergency warning and itunes and usb logo.
3. Straight away open redsn0w 0.72 and select the same firmware file. It will surely select it OK.
4. Go through this process very carefully, specially when it comes to pressing power buttons n home etc, just when it tell u to turn off phone n connected, put ur one hand on next button with mouse n other on power button of iphone otherwise u gona mess everything. This is the most important step towards jailbreaking.
5. And now comes the real point, in redsn0w it gives u option of installing cydia and icy. Now let le explain something to let u know reasoning.
I am not a MAC user but after so much hit and trial methods I have come to some conclusions that there are some MUSTs in using iphone, there might not be any logic behind but it does work in that way…
DO NOT install icy software, just check only cydia for installation, cuz one time I installed both and I got that both are conflicting with eachother too much, if I add some source to cydia, either cydia don’t recognize it or icy. For example I tried to install winterboard from cydia, it showed me errors and then I installed from icy n it installed.
in SHORT, in my view, both cydia and icy are SAME things, just in icy they have improved some GUI otherwise still cydia has more options than icy. And whatever u need in icy is present in cydia and even much more softwares. And easier to use….
6. So without installing icy, install ONLY cydia. (later I observed on 2nd time restoring my phone, that when there is cydia alone, it runs way faster n smoother n no errors at all)
7. 1st install winterboard from cydia and reboot phone n apply its 3 options, background wallpaper, user lock , and transparent dock and it will apply n then uncheck user lock…
8. Now install openSSH from cydia.
9. The basic purpose of my telling this is, that install everything u need from cydia, I dun use cydia softwares much, just there are some fixed list which I install so install everything n AT LAST add ultrasn0w and install it but before this a reboot is recommended to let everything go smooth.
10. And now u will not feel any problem at all, winterboard is running fine on my iphone without any problem at all. In my opinion this software ICY is buggy and conflicts, so I dun use it, I have only cydia and its enough to me. Even if u dun use icy, it conflicts. So dun even install it.
IF u liked this post and it solved ur problem. Kindly appreciate it.

