Why is it difficult to hit the OB straight when both the CB and OB are frozen to the same cushion or rail?

First of all, to have the OB hug the rail, a very accurate hit is required. Also, the cushion must be true, with no bumps or waves. Also, the faster you hit the shot, the more the CB will bounce due to the cue elevation required for the cue to clear the head rail. When the CB bounces off the table, it will deflect off the nose of the cushion some away from the rail since part of the CB is actually under the nose of the cushion when it is frozen to the rail. For demonstrations, see the following videos (and the videos below):

One option to improve accuracy on a shot like this is to hit it as softly as possible to minimize how much the CB hops. Another option is to use a touch of inside english (with the right cue elevation for the given shot speed) to squirt the CB away from the cushion and have it swerve back toward the rail. And if the CB doesn’t quite swerve back enough, spin-induced throw helps straighten the OB. All options and approaches, along with example game-situation shots are demonstrated in the following videos that include a clip from Vol. V of the Video Encyclopedia of Nine-ball and Ten-ball (VENT):

On table with a worn “rail groove,” the OB will tend to be drawn back to the cushion after it bounces away slightly with slow speed. And a slow-rolling ball is also more likely to bounce away from the cushion due to dirt or cloth irregularities. This can increase the chances for a slow-rolling OB to hit a side pocket point if it happens to be returning to cushion just before the pocket opening.

Here are some interesting shots with two balls frozen to a rail, relying on cushion compression and double kisses:

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