By default only 10 documents are returned, which I assume could all be from the most recent index. To get more data you need to specify the size, which can not be larger than 10000.
the size and from parameters to display by default up to 10000 records to your users. If you want to change this limit, you can change index.max_result_window setting but be aware of the consequences (ie memory).
Is that alias the write alias? If so it only points to the latest underlying index. Try searching winlogbeat-7.11.2-* and see if that makes a difference.
It looks like you have several thousand documents per day and are only returning 2000. Elasticsearch natural ordering may mean you do not get a random sample. I would recommend adding a date range filter to limit the serach or sort descending on the @timestamp field.
Do the same search against winlogbeat-* as thst is what you are using in Kibana. Does that return results? Do you have winlogbeat indices for multiple different versions?
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