I need to cross-compile one of the latest GDB server versions (7.4 or 7.5) for iOS. By default configure script does not support such target (arm-apple-darwin). However, I have an idea to merge Apple's open source version of GDB server (based on pretty old version of GDB) with the latest GDB version. Did anyone try this approach? May be there is a better way?
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Using mainline GDB is going to be tricky; Apple's version has been forked quite a while ago and porting it won't be trivial. Why do you need specifically 7.4?
If you just need a gdbserver for iOS, try Saurik's patches, although I'm not sure how recent they are.

Igor Skochinsky
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In general, any version starting from 7.0 will fit my needs (multithreading support, ARM NEON ISA support, etc.). However, the newer the version the better. – bsa2000 Sep 11 '12 at 16:34