Supernova (SN) 2014C is a rare transitional event that exploded as a hydrogen-poor, helium-rich Type Ib SN and subsequently interacted with a hydrogen-rich circumstellar medium (CSM) a few months postexplosion. This unique interacting object provides an opportunity to probe the mass-loss history of a stripped-envelope SN progenitor. Using the James Webb Space Telescope (JWST), we observed SN 2014C with the Mid-Infrared Instrument Medium Resolution Spectrometer at 3477 days postexplosion (rest frame), and the Near-Infrared Spectrograph Integral Field Unit at 3568 days postexplosion, covering 1.7–25 μm. The bolometric luminosity indicates that the SN is still interacting with the same CSM that was observed with the Spitzer Space Telescope 40–1920 days postexplosion. JWST spectra and near-contemporaneous optical and near-infrared spectra show strong [Ne ii] 12.831 μm, He 1.083 μm, Hα, and forbidden oxygen ([O i] λλ6300, 6364, [O ii] λλ7319, 7330, and [O iii] λλ4959, 5007) emission lines with asymmetric profiles, suggesting a highly asymmetric CSM. The mid-IR continuum can be explained by ∼0.036 M_⊙ of carbonaceous dust at ∼300 K and ∼0.043 M_⊙ of silicate dust at ∼200 K. The observed dust mass has increased tenfold since the last Spitzer observation 4 yr ago, with evidence suggesting that new grains have condensed in the cold dense shell between the forward and reverse shocks. This dust mass places SN 2014C among the dustiest SNe in the mid-IR and supports the emerging observational trend that SN explosions produce enough dust to explain the observed dust mass at high redshifts.