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I have no idea why, but sometimes when there is a gap between two clips and I choose Ripple Delete, the option for Gap is gray and is not selectable.
I have no idea if I have accidentally changed modes, or set a preference somewhere, or if it's because of the tool I have selected. It doesn't happen every time, and I'm not sure what I'm doing differently.
I'm using CC build 11.0.0.199 on a Mac using OSX 10.11.6
Reproduction steps:
Add a clip to a multitrack session
Use the razor tool cut the clip twice
Select the clip between the two cuts
Press delete on the keyboard
Right click (control click) the gap
Hover over Ripple Delete from the context menu
Notice that Gap is gray
This is only the case sometimes, but once it starts I basically can't use that feature on the project any more, which is an important part of the workflow since pressing Option Delete to delete a time selected piece of a clip doesn't move the remaining clips to close the gap, only the clip you are removing a section of will snap closed.
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I think that the Ripple Delete option that you require is Ripple Delete Time Selection in Selected Track. This will remove the selected portion of the clip and move all the clips on the right to the left to fill the gap. This doesn't have a keyboard shortcut by default but you can easily set one up in the keyboard Shortcuts menu to be able to do this operation with one click without having to Razor the In and Out points of the bit of clip that you want to remove.