Dip to Black is not really a Transition. Its a Fade to Black therefore it works on one clip.
If you want black between two clips, place a black clip (Black Video) between them and fade in and out of it.
Likely you are missing handles. Look in the help file or manual for information on handles and how it affects transitions.
If you look at the first image you can clearly see that Dip To Black does affect multiple clips, and that it is listed under the Video Transitions segment of the effects panel for a reason.
My question is why is it working for me on some clip transitions and not others.
I appreciate the response.
I checked all of the areas that I could find with regard to handles. The first clip transition, doesn't seem any
different than the next.
I'm surprised that this is an odd problem, I assumed that it would be common place. I run into it on almost every project. Most clips transition just fine, but occasionally there are ones that for some reason won't allow any transition affect to be applied to them.
Assuming you have sufficient handles on the clips, choose 'Center at cut' in the effect controls panel.
Here is a bit more info on Handles:
Also, as you note, Dip-to-Black WILL affect Clips below.
Another reason for it applying to only one Clip, even with proper Handles, is if the Clips are NOT butted-up to each other. A one Frame gap will give the results that you describe - check for any gaps, if you have the Handles.