Abstract: In most models of the dark sector, dark matter is charged under some new symmetry to make it stable. We explore the possibility that not just dark matter, but also the force carrier connecting it to the visible sector is charged under this symmetry. This dark mediator then acts as a Double-Dark Portal. We realize this setup in the dark mediator Dark matter model (dmDM), featuring a fermionic DM candidate chi with Yukawa couplings to light scalars phi. The scalars couple to SM quarks via the operator q q phi phi /Lambda. This can lead to large direct detection signals via the 2->3 process chi N -> chi N phi if one of the scalars has mass < 10 keV. We undertake the first systematic survey of constraints on light scalars coupled to the SM via the above operator, including LHC experiments, cosmological considerations and stellar astrophysics, and find the strongest constraints come from neutron star cooling observations. We also explore the direct detection consequences of this scenario and find that a heavy ~ 100 GeV dmDM candidate fakes different ~ 10 GeV WIMPs at different experiments.