The negative impact of Upper Greater Horn of Africa’s (UGHA) complex topography on drought characterization exacerbated by gauge density and model forcing parameters has not been investigated. In order to fill this gap, this study employs a combination of remotely sensed, in-situ, and model products (1982-2013); precipitation (CHIRPS, GPCC, and CHIRP), soil moisture (ERA-Interim, MERRA-2, CPC, GLDAS, and FLDAS), vegetation condition index (VCI), and total water storage products (GRACE and MERRA-2) to (i) characterize drought, (ii) explore the inconsistencies in areas under drought due to topographical variations, gauge density, and model forcing parameters, and (iii), assess the effectiveness of various drought indicators over Ethiopia (a selected UGHA region with unique topographical variation). A 3-month time scale that sufficiently captures agricultural drought is employed to provide an indirect link to food security situation in this rain-dependent region. The spatio-temporal drought patterns across all the products are found to be dependent on topography of the region, at the same time, the inconsistencies in characterizing drought is found to be mainly driven by topographical variability (directly) and gauge density (inversely) for precipitation products while for soil moisture products, precipitation forcing parameters plays a major role. In addition, the inconsistencies are found to be higher under extreme and moderate droughts than severe droughts. The mean differences in the percentage of areas under drought and different drought intensities over the region are on average 15.87% and 6.16% (from precipitation products) and 12.65% and 5.20% (from soil moisture products), respectively. On the effectiveness of various indicators, for the duration under study, the following were found to be most suitable over Ethiopia; VCI, GPCC, ERA, CPC, and FLDAS. These results are critical in putting into perspective drought analysis outcomes from various products.