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Are you searching in Regex mode?
Under regex options, what exact options are checked? Do you have Dot All set? Do you have Minimal matches set?
Your first behaviour is consistent with no Minimal match and no Dot All.
The second find test will always start where the first one ends.
And the text box will always search from the cursor slipping past any tags. That way it only detects text outside of tags. Its results depend on starting point and the tags that exist and where they are located, and of course the Regex Options that you set.
In my testing, it all works as expected given the regex options.
Please provide a sample html, and all your exact find settings indicating what you get versus what you expect to see, so we can recreate what you are seeing.
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