Silicone elastomers such as polydimethylsiloxane (PDMS) are convenient materials routinely used in laboratories that combine ease of preparation, flexibility, transparency, and gas permeability. However, these elastomers are known to contain a small fraction of uncrosslinked low-molecular-weight oligomers, the effects of which are not completely understood, particularly when used in contact with liquids. Here, we show that triple lines involving air, water, and PDMS elastomers are responsible for the contamination of water–air interfaces by uncrosslinked silicone oligomers through a capillarity-induced extraction mechanism. We investigate both the case of static and moving contact lines and study various geometries ranging from partially immersed PDMS plates to water droplets or air bubbles deposited on PDMS plates, all involving air–water–elastomer triple lines. We demonstrate experimentally that the contamination timescale is strikingly shorter for moving contact lines than in the static case. Eventually, we propose a simple poroelastic model capturing the main features of contamination observed in experiments.