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I debugged a project using gcc/g++ 4.8.1 and gdb 7.10 on Ubuntu. When debugging session was active, I set a breakpoint and set its condition. Everything worked perfectly. But when session ended, breakpoint icon changed from conditional breakpoint icon to just line breakpoint icon, and I also do not see my condition any more. However as soon as I start debugging again, condition works.
Though it is confusing, such behaviour is not a bug. When we set up condition for a breakpoint during debugging, we creating a sub breakpoint, which will be displayed in the breakpoints pane after debugging session ends.