I had the same prob. I Messed around with it for hours trying to fix it. The newest Beta Verson has fixed this glitch, but personaly I’m not ready to make the upgrade. For some reason it worked fine before I switched my buddy icon settings by unchecking the checkbox next to “Remember icon from previous conversation” under the Miscellaneous heading.

But anyways, heres my temporay Solution for Trillian PRO 2: (REMEMBER TO BACK UP ANY ALTRED FILES FIRST)
Stage 1:

– In Trillian load up the Preferances, and click on the Buddy Icon selection.
– Under the “My Buddy Icon” heading uncheck the box next to “Use one icon for all connections”.
– Now using the now accessible dropdown menu set your icon indvidually. (You can set them all to the same icon just make sure it is down this way. And for msn, yahoo, icq you no longer have the size constraint so you can make the image anysize you want since it is only AIM that has that rule)
– Make sure that under the Accept Icon heading the two options are set to “always” (and i hope for your sake you have an decent antivirus)
– And under the Miscellaneous heading box check boxes are cheked.
– Now FIRST click APPLY
– Now Go to the Profile Settings and find out what the name is of the profile you are using. MAKE NO CHANGES!
– Now APPLY again and OK, Then close/Exit/Shutdown, whatever you call it, out of Trillian completely. Make sure you do this!

Stage 2:
– In windows explorer locate the “users” folder that is in the Trillian folder. (Should be “C:Program FilesTrillianusers” )
– Now if you didn’t change any other the default profile settings, you are the only user of trillian and still didn’t change the profile setting then you should see a folder called default otherwise look for a folder that has the name of the profile you use that we checked earlier. If you have more then one profile try to make sure you select the one that is giving problems. In my case i had the default folder. What we are looking for is not in the folder marked “global”
– Within your profile folder the should be another folder called “buddyicons” open it.
– Now delete all files that are “MS-DOS Application” usually look like “MSN-joe@hotmail.com”
– Now return to the previous folder
– Locate the “msn.ini” file and open it. it should run in notepad(If your computer prompts you to open it with… select Notepad and if it doesn’t run notepad then drag and drop)
– Scroll down until it reads [icon hash] close to the bottem of the file and remove everything after the tag [icon hash]
– Save the file and restart. Yes i said restart your computer

FINISHED

Now you should not run into the problem again. I have not but if you do sorry make but you got to redo all this. HAVE FUN! 😀