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Hi!
2. The most likely cause is that the Free version of the media parser is limited to 10MB per file. In this case the parser is bypassed for files over 10MB and the plugin automatically uses the local parsers. For large files like 30MB+ it can take a lot of time and a huge amount of memory to process, and the server may time out – which could lead to the error 500 code.
On the other hand it does not mean the process does not finish (only the response takes so much time, that it reports an error), from the screenshots I am almost 99% sure the indexing finished, as it shows that all files have been indexed and the amount of keywords is very high.
Listing the files is not possible on the back-end, you can check the database if you want to, in the wp_asp_index table if you group or select distinctively by the “doc” column, that will list you the post/attachment IDs indexed:
SELECT doc FROM 'wp_asp_index' GROUP BY 'doc' ORDER BY 'doc' DESC
The stats on the screenshot also say that there are 0 items not indexed, so it should be okay.
3. It is possible to show the context in the live results, but only if the file contents were parsed via the media service feature, as that is the only way to get accure file contents. That is then stored locally and used as the content field. In your case the local parser is used because of the file sizes, so that will not work unfortunately.