_With Spanish-ISO keyboard (accent under ')_.
Case 1:
<h2>Headin[]g 1</h2><h2>Heading'[]g 1</h2>Case 2:
<p>Hea[]ding 2</p>y<p>He<strong>y</strong>´ding 2</p> and Throws TypeError: null is not an object (evaluating 'viewBlock.parent') in _defaultToModelPosition — mapper.js:222With auto correct turned off, everything works fine in the above cases.
I couldn't reproduce it but my Safari behaves a bit differently than @f1ames's. On his macOS the word is underlined with blue dotted border. On my with red. This means that some other system kicks in.
It seems it may be more related to autocorrect than IME itself:

Also confirming that above scenarios are still reproducible:

Ok, I was able to partially reproduce the scenarios shown above (https://github.com/ckeditor/ckeditor5-typing/issues/85#issuecomment-368893835). You have to turn on the autocorrection in Safari:

But it behaves a little different than before so I suspect something changed after Safari/macOS update:
<p>Hea[]ding 2</p>.a.<.Hea is replaced with Hey by autocorrect. This is not an issue as no errors are thrown, this is the way autocorrection works. I was not able to reproduce any of two initial scenarios (looks like autocorrection doesn't kicks in that easily while typing inside a word).

I'm closing this issue as it is not reproducible any longer.
_Not sure how we should label it in this case?_ cc @Reinmar
Not sure how we should label it in this case? cc @Reinmar
As fixed. Someone fixed it :D
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As fixed. Someone fixed it :D