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I've got a trigger that invokes a call to a external service, passing along opportunity data, via a queueable apex class. Most of the time this call would pass, but say my external system goes down, and some of these calls fail.

What kind of process should I put in place that would run maybe hourly, find all the failed queue items, and retry sending over that opportunity data? Would this need to be a batch job that runs every hour, and if so, how do I access the queue?

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If your call to the external webservice is simple and straight forward, then use the combination of Workflow & outbound message. This out of the box functionality allows retry mechanism hourly & upto certain number of times.

If above approach doesn't seem to work then, probably once an error response is received you might have to store this response in a custom object and then write a batch apex job which looks in this object and retries the webservice calls.

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