Is it possible to get commercial skipping to work with Chromecast?
Chromecast is unfortunately the black sheep in the Tablo family. Hardly anything works well with it, and I would not recommend it for any Tablo user.
Now when commercial skip works with web apps, it should also work with Chromecast by default. Chromecast is just a pass through device, so all the functionality really depends on what main device you are using.
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