Offsets

I am having issues creating an offset for a monogram. I am using the swirl mono font and it seems that when I decrease letter spacing to put letters together like a monogram should be it will not create the offset. If letters stay apart then it will create the offset. Does  anyone know a way around this?

Hello,
Hatch does not have a font called "Swirl mono".  Is this something you have purchased from a 3rd party?

It should not make a difference of the spacing if you are wanting to create a border.  Let's check your settings.
In the Outlines and Offsets dialog.........
uncheck "object outlines"
check Offset Outlines
Offset: how much you want the border to be from the outside edge of the letter.
Offset count: 1
Multiple objects: use the Common offsets (2nd image icon)
Corners: most likely for a swirl type of font you'll want the first one, round corners
Uncheck  Include holes
OK

If this is not working for you, then please send your monogram letters to support and create a ticket and we will look at it there.

Sorry it is a purchased font from The Deer's Embroidery Legacy. I was given credits there when I purchased the software. 
All settings are exactly like you stated. It does not make a difference when creating an outline; it works. Only have a problem when creating an offset.

That's fine.  I just was not finding it and not sure what you were referring to.  Open a support ticket and include the design that has the letters you are using.  Also give me a detailed description of what you are wanting to achieve in the end.