Make sure Inset is not set to Individual and also make sure that you don't have any so-called 'Double Vertices"; Select all (in Edit Mode) with 'A' and then M. Merge > By Distance.
If this doesn't help, could you post one or more Screenshots?
Omar Domenech
replied
Yes, a screenshot would be helpful or give us more context to your problem so we can help out. Even more helpful is a screengrab video so we see exactly what may be going on.
Thank you all for the responses. As I was making the screenshots and video to upload. It started working as it should. I am new to 3D modeling and well... I have no clue what I was doing wrong and or what made it start working correctly.
Martin Bergwerf
replied
Hi Brandon,
My guess is, that it's because of the times you pressed I...the first I is for Insetting, each consecutive I (during the operation), Toggles 'Individual Faces' on and off.