Cortana not showing photos in reminders

I am having trouble with the pictures not showing up in Cortana when reminding me of a particular event.
Screenshots are provided below for your reference, but personal info is blurred out for your privacy.

The picture on the left is what is expected.
The picture on the right is what I am getting for reminders.
Is there something wrong with the pictures not displaying in Cortana? It also appears on all my computers.

Yes i did. It is in my hard drive

After multiple tries, I got it working after realizing the drive showing the pictures weren't available.
It now shows below

Notice the picture is now added.