Outlines on text breaking regardless of outlining

As suggested, you will have to change stroke to an offset, or manually deleting the extra "holes"

What is happening is your stroke is bigger than the object it's applied to, and strokes are centered on the path, so while half the stroke is going outward, the other half is going inward. In the case of the "dot" it's going past the edge of the dot in the opposite direction, and this path is being drawn in the opposite direction (due to a thing called winding direction) so it's essentially cutting a hole. There's no "fix" for it per se. That being said, this phenonemon mostly affects curves, especially those in a compound path like a font letterform, but its not limited to that.

It looks like there may be an errant anchor point or a couple of them doubled up at one location on the path. I prefer using the Offset Path effect for letter outlining effects rather than using line stroke. There are fewer paths to clean up when expanding the effect into editable paths (no doubled paths on the insides of letters). With an outline that thick it might be necessary to apply the effect separately to a few letters at a time. That would let you see which letter is causing the odd overshoot problems. If the effect is expanded the glitch can be edited using various tools.

Hi @lidm,

Thanks for reaching out! This seems to be a file-related issue. Could you share the file with us? You can upload it to Creative Cloud or a similar service like Dropbox and share the download link.  

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Regards,

Srishti