We have a pretty major application suite for a client with a couple application targets utilizing several static libraries that we made in house. All targets are contained in on
This appears to be fixed in a later version of XCode, currently using 4.6 and the problem went away.
If you are stuck using an older version then do the following: Product > Build For > Archiving Product > Archive Open the built product from derived data, you can do this by right clicking on the Youapp.app file in Products group and selecting show in finder. Ensure you are in the Release-xxx folder. Copy the dSYM file generated there and replace the one produced by the archive process. To find where archived files are go to Organizer, Archives tab, right click on an item and show in finder.
Hope this helps.