This issue was introduced in https://reviews.llvm.org/D92187.
The guard I'm changing were is supposed to act when linux is loading the linker for the second time (due to differences in paths like symlinks).
This is done by checking module_sp != m_interpreter_module.lock() however this will be true when m_interpreter_module wasn't initialized, making linux unload the linker module (the most visible result here is that lldb will stop getting notified about new modules loaded by the process, because it can't set the rendezvous breakpoint again after the stepping over it once).
The m_interpreter_module is not getting initialize when it goes through this path: https://github.com/llvm/llvm-project/blob/dbfdb139f75470a9abc78e7c9faf743fdd963c2d/lldb/source/Plugins/DynamicLoader/POSIX-DYLD/DynamicLoaderPOSIXDYLD.cpp#L332, which happens when lldb was able to read the address from the dynamic section of the executable.
What I'm not sure about though, is if when we go through this path if we still load the linker twice on linux. If that's the case then it means we need to somehow set the m_interpreter_module instead of the fix I provide here. I've only tested this on Android.
Delete, and use self.registerSharedLibrariesWithTarget in python code