In　terms　of　interlayer　trions,　electronic　excitations　in　van　der　Waals　heterostructures　(vdWHs)　can　be　classified　into　Type　I　(i.e.,　two　identical　charges　in　the　same　layer)　and　Type　II　(i.e.,　two　identical　charges　in　the　different　layers).　Type　I　interlayer　trions　are　investigated　theoretically　and　experimentally.　By　contrast,　Type　II　interlayer　trions　remain　elusive　in　vdWHs,　due　to　inadequate　free　charges,　unsuitable　band　alignment,　reduced　Coulomb　interactions,　poor　interface　quality,　etc.　Here,　the　first　observation　of　Type　II　interlayer　trions　is　reported　by　exploring　band　alignments　and　choosing　an　atomically　thin　organic–inorganic　system—monolayer　WSe2/bilayer　pentacene　heterostructure　(1L + 2L　HS).　Both　positive　and　negative　Type　II　interlayer　trions　are　electrically　tuned　and　observed　via　PL　spectroscopy.　In　particular,　Type　II　interlayer　trions　exhibit　in‐plane　anisotropic　emission,　possibly　caused　by　their　unique　spatial　structure　and　anisotropic　charge　interactions,　which　is　highly　correlated　with　the　transition　dipole　moment　of　pentacene.　The　results　pave　the　way　to　develop　excitonic　devices　and　all‐optical　circuits　using　atomically　thin　organic–inorganic　bilayers.