In the context of civilian and military communications, anti-jamming techniques are essential to ensure information integrity in the presence of malicious interference. A conventional time-domain approach relies on computing the Wiener interpolation filter to estimate and suppress the jamming waveform from the received samples. It is widely acknowledged that this method is effective for protecting wideband systems against narrowband interference. In this work, this paradigm is questioned through the design of a $K$-tone jamming waveform that is intrinsically difficult to estimate assuming a $L$-tap Wiener interpolation filter. This design relies on an optimization procedure that maximizes the analytical Bayesian mean squared error associated with the jamming waveform estimate. Additionally, an analytical proof is provided showing that a multi-tone jamming waveform composed of $L/2+1$ tones is sufficient to render the Wiener-filter-based anti-jamming module completely ineffective. The analytical results are validated through Monte Carlo simulations assuming both perfect knowledge and practical estimates of the correlation functions of the received signal.