I can confirm this. Also, the space (" ") returns font.MeasureString().X value of 0. In XNA, it would return the actual width of the space (I'm guessing based on whatever the maximum character block would be).

This is not related to the actual topic, but:
@xanather may i ask how you are doing this red outline rendering? do you just offset it 4 (or 8) times when before drawing the black font? or do you have some shader in place?

I first draw the red outline (4 drawstring calls) at offsets (-1, 0), (1, 0), (0, -1), (0, 1) and then draw the black text over it (no offset).

https://github.com/sharpdx/SharpDX/blob/master/Source/Toolkit/SharpDX.Toolkit.Graphics/SpriteFont.cs#L402 Is this the issue? I have a feeling its not the actual imported Glyph measurements since all characters can be drawn/measured fine IF they are not the first character.

Any thoughts as to why this might happen? Its the only bug ive found on SharpDX TK and I rather would not code around it.

I had no time to look into this. This code is inherited from SpriteFont from DirectXTk. If you take the time to dig into this issue and fix it that would be helpful

Well I do owe this project alot, I will give it a shot. This is also a time for me to solve the requirements on compiling on Windows 7.

Edit: I was copying over the Input library instead of the Graphics library, silly me :) Should have fix soon

Issue stems from the change at #86 060f9b7

Thanks, I did some tests but the fix was not working well with fixed fonts and spaces at the beginning of the line.
After checking and using the same rule as DirectXTk, It is working well with fixed font like "Courier New" as well as "Arial". Let me know if there is still an issue

Edit: going to make another issue.