Video/Audio Transitions
There are 5 ways to apply transitions.
By default Apply Transition command will be used with default transition duration (could be set in Premiere Pro>Preferences>Timeline
).

Apply Transition
Applies transition to cuts under playhead. If cuts are selected, transition will be applied to them, If clips are selected, transition will be applied to in/out points of selected clips.

Apply Transition To/From Playhead
Applies transition to cuts on the left/right of playhead and stretches transition to playhead position.

In comparison to legacy version, "Apply Transition To/From Playhead" adds proper transition between clips.
"Apply Transition To/From Playhead" command presses Select Clip at Playhead shortcut. Make sure it is assigned in Keyboard Shortcuts menu.
Apply Transition To/From Playhead (legacy)
Applies transition to cuts on the left/right of playhead and stretches transition to playhead position. (Standard Premiere Pro command)

"Apply Transition To/From Playhead (legacy)" doesn't add transition between clips, but adds fade to/from black/silence.
"Apply Transition To/From Playhead" command presses Apply Default Video/Audio Transition to/from Playhead shortcuts. Make sure they are assigned in Keyboard Shortcuts menu.
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