Re: is this a bug, or am I just confused?
If I guess correctly what's happening, the problem you're having is
that dpkg-shlibdeps doesn't consider the current contents of
debian/shlibs when determining shared library dependencies.
It doesn't matter how many times you build the package in question:
all that matters is the version of the shlibs file that is installed
on the system.
My general solution to this problem is to duplicate the contents of
debian/shlibs in debian/shlibs.local for any package that provides
both binaries and shared libraries in the same package. A number of
other solutions are possible as well --- that's just the one I happen
to use in my own packages.
Other possible solutions are to use the -T option to dpkg-shlibdeps,
to symlink debian/shlibs.local to debian/shlibs, or just to name the
file to be copied into <package>/DEBIAN debian/shlibs.local instead of
debian/shlibs.
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