(1) Background: Indwelling pleural catheters (IPCs) with vacuum-based drainage can cause pain, especially in patients with a non-expandable lung (NEL). This evaluation assessed whether the Passio™ digital drainage system offers a viable alternative for patients experiencing pain during IPC drainage. (2) Methods: All IPC patients between November 2023 and April 2024 completed questionnaires assessing pain severity on a 10-point visual analogue scale (VAS) at four points during drainage. Patients reporting drainage-related pain at the 2-week post-IPC appointment had their existing valve replaced with a Passio™ valve (n = 5). (3) Results: Twenty-seven patients (59% male) were included in this analysis. The mean VAS scores for pain with a standard vacuum bottle were not statistically different at mid-drainage and the end of drainage compared with pre-drainage. Patients who experienced pain with the vacuum bottle (n = 5) had higher mean VAS scores at mid-drainage (51.68 mm ± 16.29; p = 0.13), end of drainage (46.68 mm ± 19.45; p = 0.19), and 10 min post-drainage (61.38 mm ± 9.81; p = 0.06) compared with pre-drainage (9.16 mm ± 4.01). Post-Passio™ valve replacement (n = 5), patients had a lower VAS pain score mid-drainage (20.15 mm ± 9.34; p = 0.25), end of drainage (27.28 mm ± 12.69; p = 0.84), and 10 min post-drainage (14.81 mm ± 3.33; p = 0.0079) when compared with vacuum bottle drainage. There were no complications with the Passio™ drainage system. (4) Conclusions: Controlled pleural drainage using a digital drainage device such as Passio™ may have a role in IPC patients who experience pain with vacuum bottle drainage, especially in those with an NEL.