Redstone wire not updating as it should!

This is a very annoying glitch where redstone isn't getting updated like it should.

What I expected to happen was...:
I expected the redstone to update 😛

What actually happened was...:
It didn't.

Steps to Reproduce:
The simplest example of it is in the attached pictures.

1. Build whats in the first picture.
2. Power the second repeater like in the second picture and notice how the redstone isn't updating properly.