We present SN 2019tsf (ZTF19ackjszs) and SN 2019oys (ZTF19abucwzt). These two stripped envelope Type Ib supernovae suddenly showed a (re-)brightening in their late light curves. We investigate this in the context of circumstellar material (CSM) interaction with previously ejected material, a phenomenon that is unusual among SE SNe. We analyse observational data, consisting of optical light curves and spectra. For SN 2019oys we also have detections in radio as well as limits from UV and X-rays. Both light curves show spectacular re-brightening after about 100 days. In the case of SN 2019tsf, the re-brightening is followed by a new period of decline, and the spectra never show signs of narrow emission lines that would indicate CSM interaction. On the contrary, SN 2019oys made a spectral makeover from a Type Ib to a spectrum clearly dominated by CSM interaction at the light curve brightening phase. Deep spectra reveal a plethora of narrow high ionization lines, including coronal lines, and the radio observations show strong emission. The rather similar light curve behaviour indicate CSM interaction as the powering source. For SN 2019oys the evidence for a phase where the ejecta hit H-rich material, likely ejected from the progenitor star, is conspicuous. We observe strong narrow lines of H and He, but also a plethora of high ionization lines, including coronal lines, revealing shock interaction. Spectral simulations of SN 2019oys show two distinct density components, one with density > 1e9/cm3, dominated by somewhat broader, low ionization lines of H I, He I, Na I and Ca II, and one with narrow, high ionization lines at a density about 1e6 /cm3. The former is strongly affected by electron scattering. The evidence for CSM interaction in SN 2019oys is corroborated by detections in radio. On the contrary, for SN 2019tsf, we find little evidence in the spectra for any CSM interaction.