Thanks for your fast replys ;0) Hopefylly we will find a solutionfor this problem.
Try out my test installation:
I started from scratch with a test installation.
I am using SS version 2.2.2 (just downloaded + a clean install)
Status so far:
1. I have tried to paste the the url from the properties dialog box into my browsers address and i dosen't work.
2. I have tried to change the path to the missing image by right click + insert/edit link and write the url directly to the SilverStripeLogo.png file.
3. I can confirm that GD2 extension is installed on my webserver.
4. I cannot from the filesystem in SS browse the file path shown in properties dialog.
5. The Upload folder has file permission 777. And I have tried file permissions 644, 755 and 777 on the upload folder and the resampled folder aswell.