Since the Obi device converts the touch-tones to digital, I wouldn't overly worry about people overhearing them, or my conversation.
I *would* worry a lot more about the casual use of wireless handsets to conduct such business, as that *could* be listened in on. But VOIP? Not without an additional DAC and suchlike.
However, you can't simply turn your back on IVR, saying you won't use it. This isn't practical in this era. IVR systems save buckets of money and enable customer service at a much higher level.
At some point in the path from you to the bank, your analog signal is certainly digitized. Odds are very high that the bank has digital service -- a T-1 or at least a partial, however tiny the bank. Staying entirely analog from your phone to the bank is a vanishingly rare phenomenon. Quite likely it's converted to digital at your local hub, in your backyard or your neighbor's. The odds, or the point at which the signal might get intercepted, aren't significantly different either way.
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But what I do find, is that the setting won't "stick". That is, I'll find that tones aren't working anymore, getting erratic results, so I log back into my OBI100 and find that the setting has reverted to "Auto" from "Inband".
I would change the password on the OBI if I could, but this also reverts every time I attempt to change it.