After the cardinal points connection was added for lp:1840721, rotated pads can be connected by overlapping cardinal bounding box points (but not pads) as in the attached file.
Application: KiCad
Version: (5.99.0-145-gb7128639f-dirty), debug build
Libraries:
wxWidgets 3.0.4
libcurl/7.64.0 OpenSSL/1.1.1c zlib/1.2.11 libidn2/2.0.5 libpsl/0.20.2 (+libidn2/2.0.5) libssh2/1.8.0 nghttp2/1.36.0 librtmp/2.3
Platform: Linux 4.19.0-5-amd64 x86_64, 64 bit, Little endian, wxGTK
Build Info:
wxWidgets: 3.0.4 (wchar_t,wx containers,compatible with 2.8) GTK+ 3.24
Boost: 1.67.0
OpenCASCADE Community Edition: 6.9.1
Curl: 7.64.0
Compiler: GCC 8.3.0 with C++ ABI 1013
Build settings:
KICAD_SCRIPTING=ON
KICAD_SCRIPTING_MODULES=ON
KICAD_SCRIPTING_PYTHON3=ON
KICAD_SCRIPTING_WXPYTHON=ON
KICAD_SCRIPTING_WXPYTHON_PHOENIX=ON
KICAD_SCRIPTING_ACTION_MENU=ON
BUILD_GITHUB_PLUGIN=ON
KICAD_USE_OCE=ON
KICAD_USE_OCC=OFF
KICAD_SPICE=ON
KICAD_STDLIB_DEBUG=OFF
KICAD_STDLIB_LIGHT_DEBUG=OFF
KICAD_SANITIZE=OFF
I've fixed this to handle rotation.
Note however that the algorithm is still sparse; if you move one of the pads in the example so that just the corners touch you won't get a connection. Still, it's better to give a false negative (which DRC will catch) than a false positive.