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[jjjasper]

I import .flac files that I purchase online. The cover art is in the same directory as the .flac as a jpg, usually between 1200px and 3000px square. Normally, if I add cover art from a file it works well but about 2% of the time cover art can not be added, I've tried simplifying filenames, reducing the size of the cover art, and nothing seems to work for certain files. This happens to me sporadically. When I import an number of files some of them may work and others not.

[JimH]

Sounds like something odd about the FLAC file.  Try converting one to some other lossless format, just as a test.  If it works, convert it back to FLAC.

[Cinelder]

I import .flac files that I purchase online. The cover art is in the same directory as the .flac as a jpg, usually between 1200px and 3000px square. Normally, if I add cover art from a file it works well but about 2% of the time cover art can not be added, I've tried simplifying filenames, reducing the size of the cover art, and nothing seems to work for certain files. This happens to me sporadically. When I import an number of files some of them may work and others not.

I don’t know if this is relevant to your situation, but I’ve noticed whenever I have had trouble manually adding/embedding cover art,  the number of characters in the file path to the audio file was too long (over 256 characters in Windows 10 by default, I think).

For me, the fix was just moving and/or editing the file or folder name to reduce  number of characters in the path.

[HPBEME]

I ran into an issue a couple years ago where I couldn't replace the low resolution thumbnail with a better, high-resolution version for a number of different albums.  No matter what I tried, it just would not let go of that lo-res thumbnail.

Turns out the problem was when I converted a single large FLAC files into multi-track FLAC files using CUEtools (see pic below), I had the Embed Folder.jpg checkbox enabled. Apparently that setting embeds it to the point where it cannot be overwritten.  So I unchecked it, re-converted the single FLAC to a multitrack FLAC again for a handful of problem albums. After that, I was able to add high-res thumbnails to all of them with no issues. 

It does not really sound like that's what you're encountering, but thought I would throw it out there anyway as something to consider.