Synchronizing elastic search with relational database

I'm new to elastic search and evaluating a need to synchronize data from relational database to elastic search.

This article provided a solution to achieve it -

This solution seem attractive to me as its low level and avoid writing explicit code to synchronize data in elastic search.

I have few questions though:

Can logstash handle failures like elastic search being down for some reason & guarantee delivery atleast once on such scenarios when its back up ?

Whats the best way to monitor such process to ensure its synchronizing ? Appreciate to any pointers on best practices or documentation.

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